Author’s Note: As usual, a long slow backstory begins this opus. If that’s not your thing, just stop reading now. I put this story in the BDSM category, but there is definitely more submission and less bondage than most of my stories.
My name is Alexis and I am a trophy wife. No, that wasn’t my life’s ambition and honestly, I didn’t want to admit it at first, but in truth, my marriage was more of a business arrangement than love. You see, I am 34 years old and my husband is 56 and wealthy. People would say I married for money whether I admit it or not, but when you hear my story, maybe you will understand.
First off, I am a nymphomaniac. I first admitted that in college. From the moment I lost my virginity, I knew I loved sex. Not only the physical act and the endorphin rush from orgasm, but also the attention men gave me, especially since I learned from the first time I gave a blowjob that having a hard cock in my mouth was a huge turn-on. Not that I didn’t like it when a guy went down on me, but just having him in my mouth for a couple of minutes made my pussy get wet enough to fuck. When I left home for college, it is safe to say I was more excited about being out from under my parent’s watchful eyes than about the education aspects. That’s not to say I was a bad student. It’s just fucking was my real major and I juggled multiple boyfriends while I pursued my physical education degree.
Being a Southern California girl (San Diego) growing up meant I spent a lot of time at the beach and in the gym, so doing physical fitness as a career seemed like a good choice. I’m about 5′ 5″ tall and very lean. I am toned, muscular (although not like a bodybuilder) and cardiovascularly strong. I could easily outlast any of my partners in bed. The only thing I lacked was large boobs. Growing up I didn’t have the reserve fat levels to really have them develop. But my nipples were exceptionally sensitive and I gladly would exchange the pleasure of nipple play for some guy mauling larger breasts. But I digress.
In college it was easy to find men to fuck 4 or 5 nights a week. After graduation… It was still pretty easy. But I needed this thing called money and I quickly learned my degree was not exactly a big cash cow. I worked at a gym and did personal training on the side. The pay was bad as lowly gym staff, but at least the side gig doing personal training made up for it and I didn’t have to worry about being homeless. The gym closed at midnight, although we locked the door at 11pm. By then, people were just finishing up their workouts and hitting the showers. The manager was always gone and I or one of the guys that worked there had the late shift to lock up. That also meant I had time to workout at night. The manager didn’t mind if I worked out after about 10 as long as the customers were taken care of and I clocked out on time.
I was still maintaining a stable of friends with benefits to take care of my other physical needs. I always made it clear that I had no desire to be in an exclusive relationship. I was perfectly happy to be their side piece provided he demonstrated skills in the bedroom. But some nights, especially when I worked the late shift, none of my guys were available. I guess that is the downside to being non-exclusive. If I was at the gym, after it had cleared out, I would finish my shift by riding one of the exercise bicycles. Specifically I would choose one of the upright style bikes with a small seat that I could tip the front upright. Thirty minutes riding the bike rubbing my pussy on the front of the seat always left me as a dripping mess. I would then head to the employee locker room where I kept a dildo and bullet vibe in my bag for just such an occasion. If I was especially horny, I mean, I was always horny, but if I didn’t get laid the day before, I sometimes started my bike routine before the other patrons had left. Leaning over the handlebar and grinding myself on the seat, I knew the guys would be watching, but I found that exciting. I never fucked a guy at the gym. I think management would frown on that. But it was exciting to think about it. I imagined some strong guy watching me masturbate on the bike and then after the gym cleared out, lifting me down to the floor and fucking me.
For a decade, that was my life. Work, sex, food, sex, sleep, sex and occasionally cleaning my apartment and doing laundry. I knew marriage wasn’t my thing as I had yet to find someone willing to accept my need for sex meant one guy likely couldn’t satisfy me. Maybe I just had not found the right guy yet. While my friends with benefits were happy to stay casual, none of them were marriage material. Then I met Charles. No it wasn’t love at first sight. In fact, he was just another personal training client. Most of them started with me just to be able to look at me when I helped them work out. Charles was 22 years older than me. Although he was in pretty good shape for his age, I really didn’t do the whole “daddy” thing and immediately dismissed him as a potential partner. But it turns out, he really was just hiring me to help him get in shape.
Charles owned a very large and very successful commercial building company. He explained that when he worked more in the field as he built his company, he got a solid workout as a by-product. But now, as an executive, finding time to get to the gym was tough, especially since he frequently traveled around the country for meetings and to monitor build sites. I asked him if he used the gyms in his hotels and he admitted that he tried, but didn’t necessarily know what he was doing and needed help understanding what he should be doing when he was on the road.
“You should be fucking more, It builds muscle tone.” I quipped before I realized I said that.
That was entirely inappropriate to say, especially since we had just met. But he didn’t seem upset and even replied, “Is that how you stay so toned?”
I laughed that off as a joke instead of him hitting on me. “Yes, but also working in a gym helps.” I replied.
“You’re a lot like my wife,” was his next reply. I let the conversation drop and got focused back on our session.
I can always tell when someone is serious about their fitness and Charles definitely was genuinely trying to get in better shape. His travel schedule meant our sessions together didn’t have a consistent schedule, but I always looked forward to his call arranging our next appointment. We talked about all sorts of things during our workouts. He had traveled the world, was a father to twins (fraternal twins, a boy and a girl) and definitely could hold a conversation better than my boy toys. I still didn’t want to fuck him, but I felt like we became friends. I even confessed my horizontal workout routine to him. He snickered at that and reminded me that I had recommended he have more sex when we first met. He also reiterated that his wife, Sheila, was a lot like me. I wondered if he was hitting on me trying to get me into bed with them, but that subject never came up.
Over the next couple of months, our flirtations got more flirtatious, but still he never made an explicit offer to fuck me or get me in bed with his wife. I enjoyed the attention, although in a way, it was like he was teasing me. I know I had said he was too old for me, but that position was softening a bit. After one session, he showed me a picture of Sheila and she was stunning, although I thought her augmented breasts were a mistake because they took attention away from her beautiful face. But whatever. He claimed showing me the picture was because he was trying to get her to go to the gym more often and suggested that I work with her. From the look at her picture I could tell she did a lot of cardio and she didn’t look like she needed help figuring out a workout routine. But I was always one to earn more money so I told him I would be happy to meet with her.
Alas, that never happened. She was killed by a drunk driver who was coming home from a Christmas party. Fortunately nobody else was in her car. I was heartbroken when Charles told me the news. He had come into the gym in street clothes instead of changing to tell me he would be canceling our sessions for a while. I understood and immediately hugged him. I couldn’t imagine the pain his family was going through. I told him if there was anything I could do to help, to please let me know. I didn’t mean sexually. I was thinking more like food shopping or giving him or the kids someone to talk to, but upon further reflection, if he took it as a sexual offer, I might have consider accepting.
I did go to the wake. That was when I met his kids, Jimmy and Christine. They seemed to be handling their grief very well. So was Charles, at least publicly. Charles introduced me as his personal trainer. Jimmy looked me up and down. That made me feel uncomfortable, but I said nothing. We didn’t really talk as the wake was well attended and the three of them had to greet everyone.
I thought that might be the last time I saw Charles. Indeed it was for a couple of months. After New Years is always a busy time at the gym as people always show up trying to make good on their promise to get into shape. As a result, I’m work lots of overtime and sign up a lot of personal trainer clients until they give up. While the money is good, my need for sex goes largely unfulfilled except for my fingers and toys. I always volunteer to close the gym because I need time for my workout and my “special” bike rides. It was during one of those rides that Charles made his return.
It was a Wednesday night and I had not been laid since Sunday. That was not good. My boy toys were all busy and I was seriously thinking about just going to a bar after work to let myself get picked up. It was hump day after all. That wasn’t my preferred method of sexual release (I preferred my FWBs) but I was getting desperate. The gym had emptied out by 9:30 with the exception of Billy, one of the other trainers. You would think I would just offer myself to him, but I had a strict rule about not fucking other employees (I liked my job and didn’t want to risk getting fired) and Billy had a girlfriend and he didn’t seem like the kind of guy who would cheat. It’s too bad though, because he was very handsome. He left at 10 telling me he would lock the door behind him. That meant I was free to hump the bike seat for a while until I decided where in the gym I wanted to get off.
I thought of Billy while I ground my pussy on the bike seat and imagined him bending me over the reception desk. Or maybe he would take me to the desk in the office. I was quickly getting aroused. Usually I get off the bike and finish with my fingers on a weight bench or sitting on a chair, but I could tell my orgasm was building and I knew I would soon climax on the bike. I even let go of one handlebar to rub my nipples through the thin tank top I was wearing. I was moaning loudly as there was nobody there to hear me. I’m sure I made quite a sight as I humped the seat, faster and faster. Then I heard the cough of someone clearing his throat. My body instantly froze, except for my head, as I turned to look at who could me in this incriminating position. As I said before, Charles was the person who caught me. At first, I couldn’t process how he got in through the locked door. Strangely that was my concern more than the fact that he was watching me. My nipples and pussy also didn’t seem to understand that getting caught should have killed my arousal.
“Don’t stop on my account,” Charles said.
“What are you doing here?” I asked breathlessly, trying not to accept his invitation to continue masturbating in front of him.
“I wanted to talk to you about starting up our training sessions again,” he replied. “I arrived as Billy was leaving and he was nice enough to let me in since we know each other. But as I see you humping that bike, I might have a business proposition for you as well.”
Business proposition? That sounded weird and I definitely didn’t want either option at that moment. I needed to get him out of the building so I could get myself off.
“I’ll have to check my calendar and see what time slots I have open,” I said as I climbed off the bike. My legs felt like rubber, both from the workout and the um, workout. But I managed to stand and pretend I wasn’t doing what he caught me doing. I tried not to draw attention to the wet spot in the front of my shorts or the glossy shine on the front of the bicycle seat.
“The gym is closed,” I continued. “You’ll have to leave. Insurance reasons. Call me tomorrow and we’ll figure out when you can start your sessions again.”
I walked past him and continued to the front door. When I got there, I had to reach up to flip the security latch on the top of the door so I could open it. That meant both my hands were above my head because I had to stretch to do it. That’s when Charles put his arms around me and took my breasts in his hands trapping my still hard nipples between his thumbs and forefingers. Before you jump to the conclusion this was non-consensual, ok technically it was, but in my aroused state, his attention to my nipples sent a shock wave through my body and I quickly pulled my raised hands down over his head and around his neck. This let me lean back into his chest and certainly acted as my consent to his touch. He started teasing my nipples and I moaned. My orgasm, delayed by his presence a couple of minutes ago, began building once again. And building quickly.
“You are so sexy,” he whispered in my ear. My pussy creamed and the sound of his voice so intimately near me. “Your pussy smells wonderful. Have you been getting enough sex?”
He then slid his right hand down my stomach and began rubbing my pussy through my workout shorts. I moaned again and pressed my butt back against him. I felt his hard cock and another wave of pleasure coursed through my body. He responded by snaking his fingers under the waistband of my shorts then under my panties. My mind was totally lost in the moment and after just a couple flicks of his finger across my clit, I started spasming in orgasm. It was a good thing he was holding me, because my arms and legs became limp, although I did manage to keep humping my ass against his groin. I think that was my way of saying he should just bend me over and have his way with me.
But he didn’t. He just held me and kept rubbing my clit and left nipple until my orgasm subsided and I got my legs back. When he finally released me from his strong arms, I spun around and wrapped my arms around his neck. I then gave him the most passionate kiss I ever remember giving. “My God, that was amazing!” I proclaimed after I broke the kiss. “I really needed that.”
He just smiled as if to say, “I know.”
I followed up with, “Take me to the office and fuck me.”
He snickered with a smile and said, “You mean you don’t want to fuck in the window?”
Spinning back around I realized he had made me cum standing in front of the glass door of the gym. I had forgotten where we were when he grabbed me. It was dark outside so I couldn’t see if anybody was in the parking lot that might have watched, but the thought that we might have had an audience was a new thrill. But that didn’t mean I wanted him to fuck me there.
Turning back around, I replied, “No, let’s go in back somewhere.”
“I don’t want you to fuck me just because you’re horny,” he replied. I’d never had a guy reject me, especially since he had just gotten me off.
“What about the proposal you wanted to discuss?” I asked.
“It would be inappropriate to discuss that now,” he answered. “How’s Friday night for a training session?” he asked. I had to try to clear the arousal from my head long enough to process what he just asked. Normally I don’t schedule anything on Friday nights, so I knew my calendar was free. Actually I had this Friday off and was looking forward to spending time with one of my FWB. So of course, I replied, “7 o’clock?”
“Fine,” he replied. He leaned forward and kissed my cheek. “You’re amazing,” he said. “Until Friday.” And with that, he walked out of the door leaving me briefly satisfied, but also still horny and needing to cum again.
This time I made sure the door was locked and I was alone in the gym. I then stripped my clothes off and got back on the bike naked. It didn’t take long for me to orgasm for the second time. And then the third.
I rode the bike for about half an hour until I was completely spent. I didn’t bother showering. I just put my shorts and shirt back on and went home to my empty apartment. By the time I got there, my head had cleared and my body finally had calmed down. I went to sleep wondering exactly what proposal he had for me. I was still a bit upset he didn’t fuck me. But thankfully I was tired enough and temporarily sexually satisfied enough not to worry about it so much that it prevented me from falling asleep.
Thursday found me back in the gym, but I admit I wasn’t focused and my thoughts were on Charles and what would happen the next night. By Friday afternoon I was becoming frazzled from sitting alone at home thinking about it. I wished I had been on the schedule so I could be working and focus on that. Yes, I could have gone to the gym and just worked out. But somehow that didn’t seem like the right choice either. I settled on going for a run. That kept me focused on exercise for about 45 minutes. Then another 30 minutes in the shower and getting dressed to go in for our training session. Absent-mindedly, I started putting on make-up as if I was preparing for a date instead of work.
Driving to the gym, I realized I put on better looking clothes than I normally would for work. I was still casual and I wouldn’t look out of place, but I definitely was trying to look sexier for him than my regular workout clothes would allow. It bothered me that I had not made a conscious decision to do that. I just did it subconsciously. I had convinced myself that I no longer wanted him to fuck me. I wanted to believe Wednesday night was an aberration because I was weak and needy. But I had to admit to myself, maybe that wasn’t true. I sat in my car outside of the gym going back and forth on whether I should just leave or wait for him to arrive. I made the decision to leave, but I didn’t. I watched the clock tick off the minutes until I saw a limo pull up right at 7. I knew he would be inside. He was always punctual. I got out of my car and started walking toward the door. He saw me and waved. He stood next to the limo and greeted me when I approached.
“Let’s skip the workout and get dinner,” he said, holding the door of the limo open. I didn’t even think about it. I gave him a kiss on the cheek and slid across the leather seat leaving him room to sit next to me. What was I doing?
It turns out Charles was a perfect gentleman at dinner, although I definitely felt underdressed wearing a tank top and shorts. It wasn’t that the restaurant was too fancy, but he was dressed far better than me. Conversation was light and low key, although he did make it known that he always understood what kind of woman I was and when he got the opportunity to finger me the other night he did not hesitate to take me. That was pretty bold. I admit, I had naughty thoughts wondering what he was capable of and whether he expected sex tonight. We didn’t fuck and he didn’t expect me to blow him. He did finger me to orgasm in the back of the limo. When we sat down he put his arm around me and I found myself snuggling against him. As we began moving, he put his free hand over my left breast and squeezed. He then used a finger to draw circles over my instantly hardening nipple. Then he repeated the move on my right breast. Then he simply pushed his fingers down under the waistband of my shorts. He rubbed his fingers over my panties for a few seconds. I did not react, beyond scooching my butt forward a bit to give him a better angle. I assumed he was looking for my consent to continue. I suppose sliding forward gave him that because his fingers slipped below my panties. I know I said I thought he was too old for me, but dang, he was masterful at using his fingers to tease me as we drove to the gym and then to make me climax as we were arriving. Much like the last time he got me off, he left me wanting more after our “date.” In truth, I wanted to fuck him, but he didn’t offer and as we said our goodnights, I was already thinking about which of my friends with benefits to call. I needed cock.
We still worked out together and he still took me on an occasional date. I did make it clear on our third date that I at least wanted to suck his cock before he fingered me. I was starting to think of him as a boyfriend instead of just another casual guy and I wanted to be sure he could still fuck. What was the point of having an older boyfriend if his cock didn’t work? We would still meet at the gym and he would pick me up. That night in the limo (I was also seeing the benefit of having disposable income) not only did I kneel in front of him and suck him off, I also climbed on top of him and rode him. That was definitely out of character for me as I knew the driver could see me in the mirror. I may fuck a lot, but I didn’t consider myself kinky or an exhibitionist. But I also wasn’t going to miss that opportunity. Charles lay back and let me enjoy myself. He also didn’t cum quickly. I appreciated that. I came twice before he told me to get back on the floor so he could cum in my mouth. It was only after he finished that I realized the car had stopped and we were back in the parking lot of the gym. While I savored the taste of cum in my mouth, I was also beet red with embarrassment that the driver would have seen what happened. Charles didn’t seem to mind.
During our next workout I asked him about the driver. He said he has been using the same limo service for years and whenever possible, he requests Tommy as his driver. He also told me his wife loved to fuck in the limo and that Tommy had always been discreet. That didn’t make me feel completely at ease, but it wasn’t like I was going to stop seeing him because of it. He had learned the most important lesson of turning me on. Be confident and tease my nipples. That would get my juices flowing and I would do most anything for you.
We continued to see each other for about three months. He now picked me up at my apartment and was even staying the night. That meant he could fuck me properly and I was definitely down for that. It also meant he didn’t hire the limo. At first I was surprised that I missed having Tommy watching us. But then I realized it was so he could stay over and that was much better. He never asked me to be exclusive, although I did cut back the number of visits to my boytoys. Not eliminated, mind you. I still had needs. But I was getting quality with Charles that let me cut back the quantity. Then something happened that I did not expect. He proposed.
You would think I would immediately reject that offer. But it turned out it was more of a business arrangement and the practical side of me, listened to what he had in mind. Then I accepted. The basic outline of the arrangement was he needed a beautiful woman by his side for business meetings and to maintain his social standing in town. I didn’t really understand beyond knowing he lived in a monetary world different from mine. I had also seen pictures of his first wife and she was definitely beautiful. Charles explained that part of her “role” was to distract people he met with to help him close deals often worth eight figures or more.
“Did she fuck them?” I asked kind of incredulously. Mind you, I wasn’t ruling it out, but I wanted to know exactly what he expected.
“No, no no,” he replied. “Be elegant and distract them with your beauty. Sheila had a way to keep them sneaking peeks at her and that would lead them to make deals more advantageous to me and my company.
“What about us?” I asked back. “Do you love me?”
Mind you I had not said I loved him and I didn’t. He explained that no he didn’t love me, but he likes spending time with me and of course, I was a great fuck. At least he was honest. That response would have been a terrible lie. I would be given a generous allowance for personal expenses and would move in with him at his mansion, although I could keep my apartment in case things didn’t work out. He also explained he understood my sex drive was more than he could satisfy and that as long as I was discreet, he didn’t mind my maintaining my friends with benefits. I did question that, but he said he travels a lot and when he wasn’t there I could have them over or visit their place like I did now. He didn’t say it, but I assumed when he was in town, we would continue our satisfying physical relationship. It was a weird proposal, but it had a certain appeal. That appeal was a prenup that included a payoff to me of $250,000 if I stuck it out the first year and additional funds if we stayed married longer. The allure of not having to worry about money at the end of the month was strong.
I looked at the financial schedule he provided, showing he planned to retire in 8 years. That coincided with his son graduating college and then having 4 years of experience before taking over the company. If I stuck it out the entire 8 years, beyond the accumulating $250,000 a year ($2 million total) if I ended the marriage I would get a bonus million. He reiterated it wasn’t his plan to end the marriage at that time, but he understood that if I was accepting his offer simply for financial reasons, he would understand if I ended it early. He also said he really loved Sheila. I didn’t know if that was to convince me that he might love me one day. Honestly, you probably know me well enough by now to know that being loved wasn’t high on my priority list, but it’s a nice thought that a sham marriage might end up well.
I looked at it as I was an employee and my job was to help him close business. If that was worth $250,000 a year to him, it was a damn sight easier than working as a personal trainer for $40-50k. I also knew I could do that job. I’d been manipulating men since puberty. I did wonder how his kids would react to me being the new wife. As Freshmen in college, I wasn’t quite old enough to be their mother. Would they understand I wasn’t a gold digger after their dad’s money? Well not after all his money and hopefully generating more revenue than I cost. I told him I had to think about it. It certainly wasn’t where I pictured my life heading.
I spent the next week making a list of objections why this wouldn’t work. Charles skillfully handled them all as the skilled salesman he was, although he added a new requirement as well. I had to augment my breasts. Having seen pictures of his first wife, I kind of expected that requirement would be added. In truth, I had thought of it before, but lacked the funds to get the surgery. I was also concerned I would lose nipple sensitivity. That was actually the bigger issue. I wasn’t going to give up that erogenous zone. Charles reassured me that Sheila had a similar concern and suggested we make a consultation appointment with the surgeon who did Sheila’s implants. I saw no harm in that.
So jumping ahead six months with planning completed for a Spring wedding. My new boobs have healed and I must admit, they look great and gave me a lot more confidence in seeing myself as a beautiful woman. That may sound shallow, but I could now wear clothes I previously had felt self conscious in because I didn’t fill out the top like the dress deserved. I also met Charles’ kids, Jimmy and Christine when they came home from college. They were both freshmen and are fraternal twins who turned 18 last fall. Christine was understandably cool to my presence. I expected that. Jimmy was more open, but it could have been because he was enjoying looking at me. In truth, I liked looking at him as well. He was young, but a hunk.
The wedding went fine. Neither kid made a scene and the small guest list was about half business associates. I was learning that everything was business with Charles. He did let me play the role of blushing bride however. Everything for the wedding of my dreams came true and we even spent a week in Hawaii for our honeymoon. Although he was on the phone more than I would have liked, Charles didn’t treat me as an employee. While I wasn’t exactly in a whirlwind romance, we did have our moments and we certainly consummated the marriage. Frequently and with vigor.
The kids had returned to school before we arrived home. I settled into the life of a trophy wife. I worked out almost every day to keep my body in shape. We had a pool at the mansion as well as an endless pool/spa and an elliptical for cardio. But I still liked going to a real gym to strength train, have various machines so I didn’t get bored and because I liked the attention guys gave me. I was always ready to play my part during a business meeting or dinner, but I was also always on the lookout for the next friend with benefits to add to my stable. Charles was pleased that I took to my role so quickly. As he prepared for his first business trip since the wedding, he reminded me that he didn’t mind me stepping out as long as I was discreet. I had not visited my friends with benefits since the wedding, but I assured Charles they had no interest in causing a business problem. He said he trusted me not to cause any issues. Charles had been attentive to my needs, but he knew I needed a frequency he could not provide. In my mind I was thinking about which of my play partners to call and which would best enjoy my new breasts.
The next morning Charles suggested I ride with him to the airport. I was looking forward to sprinting over to my first FWB encounter of his trip, but I decided it was the least I could do. When Charles suggested I wear a flimsy button down sundress without panties or a bra, I figured he wanted a sexual sendoff for his trip. Either that or he knew I’d be finding some cock as soon as he was gone. Either or both sounded good to me. As usual, Tommy arrived with the limo. I don’t think he had seen me since my surgery. He obviously approved of my new look, especially since I had the top three buttons undone so I could proudly display my new cleavage. He loaded the luggage into the trunk while Charles and I took up residence in the backseat. Even before we pulled away, Charles was teasing my nipples. I was pleased that the surgery had not changed their sensitivity in any way. As always my pussy began to gush. I did wish I had panties on to keep a wet spot from forming on my dress. On the plus side, there was nothing to get in the way of Charles’ fingers when he decided to probe my depths instead of teasing my nipples.
The ride to the airport is about half an hour. By the time we were halfway there, my dress was completely unbuttoned and I’d begged Charles to make me cum. It turns out Charles was skilled at keeping me on edge when he wanted. He had not done that during our dating times, but since getting married, it became a frequent part of our play. Although it was frustrating at first, I’d learned to enjoy his peculiar skills because in the end, I always had a great orgasm. This time he told me to get on the limo floor and blow him. That wouldn’t do anything to relieve my arousal, but as I told you, I love the feeling of cock in my mouth so I was happy to oblige him. The other thing I learned since getting married is that Charles seems able to hold back his own orgasm longer than my previous partners. That meant I got to slurp him for the remaining 15 minutes of our airport trip.
Honestly, I’d lost track of time. I figured he would let me suck him to full hardness then fuck me. But whenever I give a blowjob, that is what I concentrate on to the exclusion of all else. He kind of surprised me when I felt his cock swell and then felt the first spurt of a very large load hit the back of my mouth. Don’t get me wrong. I loved the taste of his cum. Well most guy’s cum as a matter of fact. But that meant he wasn’t going to fuck me. Still he could finger me to get me off, but when I got up on the seat I realized we were at the airport. That’s just like a man, I thought, to leave me wet and horny. But no worries. I could get myself off on the way home. It wasn’t like Tommy hadn’t seen that before.
Charles gave me a goodbye kiss, apparently not concerned that I had the remnants of his explosion in my mouth, and whispered that if I wanted to fuck Tommy, Shiela had told him that he was pretty good. I was stunned into silence and watched him exit the limo. Tommy was helping with the luggage in the trunk. Charles knew the state in which he left me. Did he want to leave me extra horny so I’d fuck Tommy? That seemed wrong, but at the same time, I probably couldn’t meet one of my FWB for a couple of hours. That seemed worse. I did the only thing I would think to do. I sat up, kept my dress unbuttoned (I did cover my breasts though in case someone looked in the window) and spread my legs. That was the view Tommy had when he looked in the rear view mirror so see if it was safe to pull into traffic. Oh, he also saw me smiling ear to ear.
He didn’t say anything at first. He was concentrating on navigating the airport traffic. I must say I was glad of that. On the rare occasions I had to drive to the airport, I hated it. I figured Charles had told him he could fuck me if he wanted. Charles knew I wouldn’t say no. Tommy also knew the mansion was empty so we could just go home. I was good with that, although as soon as we were on the highway, I anticipated getting myself off. But before that could happen, Tommy asked if I wanted to play a game. Sure. Why not?
“This game is called “The Lady and the Limo Driver,” he explained. I wondered how many women he had played this game with.
“Rule number one,” he continued. “You may stop at any time. Whether we complete the game or not, my discretion is guaranteed.”
He said the magic word, discretion. That led me to believe Charles was in on this plan. Either that, or Tommy understood that Sheila had similar restrictions as I did.
“Rule number two,” he added. “I will make a series of suggestions. You will follow them.” OK, that sounded a bit kinky.
“Rule number three,” he said. “The game will be played only within the inside of the limo.” So much for him taking me home to fuck. But I must admit I was curious about what he had in mind.
“Rule number four,” were the final words spoken before he expected me to make my decision. “We will not speak of the game again and nobody else will know we played. Do you wish to play?”
He may have been expecting an answer, but I wasn’t going to give in that easily. “Why shouldn’t I just masturbate and get myself off?” After all, I could do that in a couple of minutes even though the few minutes we had been driving had allowed my arousal to ebb a bit.
“You certainly may do that,” he responded. “I always enjoy watching you cum in the backseat. However, if you play the game, I believe your orgasm will be much better.”
That answer left me in a quandary. Charles had left me vulnerable with his teasing and then letting me suck his cock. I felt safe with Tommy, but there was something about the confidence with which he spoke that also put me a bit on edge. I liked confident men who knew what they wanted to do in bed, but I never specifically agreed to follow what they commanded. This game did sound potentially fun and Charles said Tommy was a good fuck. Oh what the hell.
“I can stop any time?” I asked, making sure we both understood rule number one.
“That is correct,” he replied. I was out of excuses and couldn’t think of a reason to say no. So I didn’t. I agreed to play.
“Very good, my lady,” Tommy began. While still confident, his voice took on a hint of lust. Or maybe that was just my pussy starting to moisten again.
“You shall begin by pulling open your dress,” he said. “I know how much you love showing off your new tits.”
He wasn’t wrong. Since my surgery, I always wore clothes that showed my new cleavage. At our business events, I always wore elegant clothes so I wouldn’t make me look like a slut, but also ones that allowed me to show I was a sexual creature. I also wore a bra so my nipples wouldn’t be as prominently displayed and a thong to catch any natural moisture as I fantasized about fucking Charles’ clients. His first suggestion certainly wasn’t something that caused me to end the game. He’d seen me naked before, although never at his command. I didn’t strip off my dress as that was not what he suggested, but I did pull it back so my breasts were exposed. Of course so were my hard nipples. I felt a flutter in my pussy as the thin fabric of the dress brushed against my sensitive tips.
“I have seen how excited you get when Charles teases your nipples,” Tommy said next. I almost began rubbing them until I realized he had not said to do so. I had cupped my breasts in my palms with my index fingers extended, but I held them still.
“Yes, they are very sensitive,” I replied. Tommy referenced Charles teasing me. I had the distinct feeling he was going to do the same.
“Do you prefer the word breasts, boobs, bosom, knockers, melons, hooters, udders, eye catchers, tits or titties when referring to your woman mounds?” he asked. I had to chuckle a bit at some of his slang terms. But his question also made me think for a moment.
“It depends on if I am having sex at the moment,” I replied. Then after a brief pause, “If not, then breasts. If yes, tits, I guess.”
“Squeeze your tits and slowly rub circles around your nips,” he suggested, although I thought of it more as a command. It was not lost on me that he chose the word nips instead of asking me what term I preferred.
He let me rub my nipples for about a minute before asking me what name I preferred for my vagina. The regular answer would be pussy, but at that moment I felt like a dirty whore (very unusual for me) as it was leaking its happy juice and the smell of my arousal hung in the air. I blurted out “Cunt!” without thinking.
“Very good, my lady,” he said calmly. “Take your left hand and run your fingers up and down your cunt.”
It felt so weird masturbating for Tommy as he described how he wanted me to touch myself. It was definitely more exciting than when Charles played with me in the limo and just let Tommy watch in the mirror. I knew I enjoyed being told what to do, but I had always done that within the confines of having my partner directly involved. Tommy, while looking at my reflection as traffic allowed, was focused on driving and I think his primary enjoyment was hearing me moan. He knew which ways I liked to touch myself (did Charles tip him off?) but kept telling me to stop whenever I got close to climaxing. I wondered what his endgame was for teasing me. For some reason, not getting myself off without his approval was exciting.
We played Tommy’s game for about 15 minutes until I was whimpering in need and repeatedly begging him to let me cum. He told me I would soon be allowed the orgasm I craved, but only if I agreed to participate in the next part of the game. Without knowing what that meant, I readily agreed. Tommy responded by passing me a small vibrating egg. He told me to turn it on and to put it in my cunt. As you can imagine, it wasn’t very powerful. Even though I was aroused to the point that any firm manipulation of my clit would have brought me off in seconds, this egg wasn’t going to do it. I slid it in my pussy and tried to position it near my g-spot in hopes that would take me over the edge. The egg wasn’t Tommy’s only escalation, however. He also passed me a blindfold and two velcro cuffs with carabiners attached to them. I had a questioning look on my face that he saw in the mirror.
“I don’t want you to cum until my cock is inside of you,” he told me matter-of-factly. He obviously assumed I wanted to fuck him, and while that is a reasonable assumption at that point, not being asked did have me questioning the game.
“I’m not sure about this,” I told him. He told me not to worry and that nothing bad would happen to me. He then added, “As I stated in the rules, you can quit at any time and I will take you home. You can then masturbate in private and get yourself off.”
He knew me well enough that I would prefer a live cock to my fingers. His repeating that I could quit the game at any time did reassure me. I questioned whether that meant he would stop after I put on the cuffs, but I knew him well enough not to be too worried. What was the worst that could happen? He fucks me, I cum, repeat a few times. I agreed to his new demands.
I first put on the cuffs. Tommy then had me reach under the seat back and find the child seat safety hooks. I’d never considered that a limo would have them, but I suppose all cars do, so why not. He then told me to put on the blindfold and then clip the carabiners to the hooks. It wasn’t lost on me that my ability to get myself off ended the moment the second cuff clicked onto the safety latch.
“I am going to drive a bit more to a place I know is safe,” he told me. So much for him pulling over to fuck me, at least for a bit. “Just imagine how sexy you look right now and how good it will feel when you finally cum.”
My sense was that he drove for about 15 minutes while the egg kept me on simmer and my lust fueled brain kept imagining different scenarios. Everytime the car stopped for a light, my heart leaped thinking this was it. We are at our destination. But then as I felt the car move forward pushing me back against the leather seat, my desire sank, if only for a moment. Tommy had said I could cum as soon as he entered me. I was so aroused I wondered how long it would take. Would I just cum, basically on his command, or would he at least have to pump me for a couple of minutes? And how long would he last? Was he as excited as I was to take me in the backseat? Strange questions run through your mind when you’re bound and horny. Was this a one time thing or would he expect it every time he drove me somewhere? Did I want it to become a regular thing? How many times had Sheila been in this situation? I tugged my wrists against the carabiners just to feel more helpless. I knew I could unclip them and get myself off at any time, but I didn’t want to. I wanted to see the game through to its natural conclusion.
Finally the car stopped and I heard the driver’s door open. About 10 seconds later I heard the rear passenger door open. A breeze filled the backseat. I shivered slightly, but it was more in anticipation than being cold. I could tell Tommy was climbing into the backseat. I suppose maybe it wasn’t Tommy. He could have driven to a friend’s house to pick someone else up to fuck me. But honestly, I didn’t care. I didn’t believe Tommy would skip a chance to fuck me, but if he did, as long as this new person had a functioning cock, I was able to be very happy.
I heard the telltale sound of a zipper going down. Then I heard the sound of a man stroking his cock. Positioned as I was, a blowjob wasn’t out of the question, but it would have been difficult and as my wrists were cuffed, a handjob wasn’t much easier. It didn’t matter. I only had to wait maybe 30 seconds longer before I felt two hands reach under my thighs and pull me toward the edge of the seat and spread my legs. The next thing I felt was the head of his cock touching my labia. Then he left go of my left leg. I’d almost forgotten he needed to fish out the vibrating egg. But before he did that, he slapped my clit with his cock. The unexpected stimulation almost took me over the edge. “Please don’t do that sir!” I exclaimed. Looking back, I am not sure why I said sir, but I followed up by confessing I could cum just from any clit play and I wanted to feel him inside of me. Two fingers slid inside of me. It was a bit of a challenge for him to retrieve the egg. It would have been easier if I had been standing. The last 10 seconds of wearing the teasing device was also the best 10 seconds. Now penetrated by his fingers, it was a challenge not to climax.
My breath was coming in short, rapid, pants as his fingers slid the egg out of me. Clearly he knew what I was feeling and he took his time pulling it out. Charles enjoyed teasing me and it was clear that Tommy did too.
“Please don’t make me wait. Fuck me. Let me cum!” I bellowed out. He didn’t respond. At least not verbally. I did feel him slap his cockhead against my clit again. Then again and again.
“No more sir,” I begged. “You’ll make me cum. I can’t help it. If you want my cunt wrapped around you when I do, give me your cock, now!”
I want to believe that my pussy was irresistible to him but whether it was or wasn’t, I needed him inside me now and prayed he would not bring me off by just hitting is cock against my clit. He paused, because of course he did, but then pressed his cockhead against the opening of my leaking love tunnel. I was operating beyond rational thought.
“Enough teasing! Fuck me you bastard!” I howled. And with one firm thrust he buried his cock into my pussy.
Did that single thrust take me over the edge? Technically no, but it was close. I squeezed my Kegels hard against his cock and I thrust my hips forward as much as my bound wrists would allow. Tommy seemed inspired and began to pound me. I couldn’t tell you which thrust triggered my orgasm. My first orgasm. But I know it was no more than five as he slid his cock in and out of me with great vigor. He fucked me right through my orgasm and has hard as I tried to grip his cock, his strength and my overflowing juices limited my ability to do so.
Usually I need a bit of time to recover from an orgasm before I can build up to a second one. That didn’t happen here. Maybe a minute after my first climax, a second wracked my body. I wasn’t ready for it. Normally I feel an orgasm building, but this time, it just hit. Then a third flowed as easily as the second. That one was accompanied by a big squirt erupting from my pussy. That also triggered Tommy. Honestly I was too consumed by my own orgasm(s) to realize he had pulled out and shot a big rope of cum up my belly and onto my tits. I wasn’t until I started to come down from my high that I noticed he had pulled out.
“What happened?” I asked.
“Your cunt is amazing,” he replied. That was a first time compliment for me.
“I usually last much longer,” he continued. I took that as a compliment as well. Then he pulled off the blindfold and unhooked my wrists. Looking around I noticed we were parked in my driveway.
“I told you I knew a safe space for you,” he said proudly. He started pulling up his pants, but I stopped him.
“Can I suck your cock?” I asked. I have yet to find a man that didn’t accept that offer. I told him I wanted to taste the mixture of our cum, but honestly I was trying to keep him hard so he could fuck me again. Alas, while tasty, his recovery time wasn’t as quick as I hoped and soon he dismissed me saying he had another client to pick up. Strangely I felt a pang of jealousy that he was leaving so quickly and wondered if his next client also played his game. Not that I expected we would have a relationship, but it would have been nice if he could have stayed just a little while.
I was glad Jimmy and Christine were not home as I did my walk of shame into the house. By the time they got home, I had showered and being the good step-mother that I am, had dinner made and ready for them. While outwardly friendly and asking about their days, my mind was really thinking back to Tommy and which of my NSA friends I could call on short notice to party tonight.
After dinner, I told the kids I was going out tonight and asked them to do the dishes. They groaned at the suggestion, but agreed to take care of cleaning up since I had cooked. I went upstairs to get dressed. Or rather undressed as instead of my casual step-mom cooking dinner not a well fucked slut clothes, I needed an easy to remove dress for quick access. Sometimes I expect my FWB to go out on a pseudo-date, but tonight was just about quick sex.
I picked a white dress similar to the one I wore to the airport because Brian, tonight’s choice to be a casual partner, would appreciate the humor of me pretending to be pure and innocent. Not that I looked innocent in it, especially without a bra. It buttoned down the front. While I left only the top two buttons loose, as soon as I got out of the house, two more buttons undone would show a nice cleavage and once I rubbed my nipples to hardness, they would be on prominent display through the thin fabric. Length wise it came down to mid-thigh. That was a little longer than I usually wore when going out, but I wasn’t wearing panties either so a little extra length was a good idea. I didn’t expect the dress would be on my body much past the time I walked through Brian’s door.
Coming down the stairs I hoped I wouldn’t run into Jimmy or Christine. They knew I had an open arrangement with their father. But I wanted to avoid any embarrassing encounter as I was clearly dressed for sex. Looking off the left side of the stairway toward the kitchen, I didn’t see either of the kids. I had a spring in my step down the final few steps and when I turned right at the bottom of the stairs to head to the garage, I ran square into Jimmy’s chest and bounced backward and startled.
“Hi Alexis,” he said. “Going out to get fucked again, I see.”
I was surprised he addressed me so bluntly and I defiantly replied, “Just going to meet up with a friend for drinks.”
While I was surprised that he had spoken to me so crudely, that was nothing compared to how surprised I was that he reached forward and cupped both my breasts with his hand and started rubbing my nipples with his thumbs.
“What the fuck?” I exclaimed while I brought my hands up to grab his hands and pull him off of me. I think he was planning for me to do that because he flipped his hands around and grabbed my wrists. Then he spun me around and lifted my hands above my head while pressing me against the wall. I squirmed back against him trying to break free, but he was stronger than me. As my ass rubbed against his crotch I started to feel is cock growing and my resolve against him draining away.
“Let go of me,” I hissed, but it was more of a request than a command. In fact, Jimmy soon took my right wrist and placed it on top of my left wrist so he could hold them both with his left hand. I could have broken away at this point, but I didn’t. I stood there submissively while his right hand possessively grabbed my right breast. As I am sure you know by now, the swelling of my nipple and lubrication of my pussy was immediate.
“Dad told me this is how he first touched you and how he couldn’t believe how wet you got just from having your nipples teased,” he said. He also switched from groping my breast to running his fingers over my prominent nipple. I knew he was right and my soft moan confirmed it. I was shocked Charles had shared that information with his son. Shocked, but not necessarily mad that he had as his hands felt wonderful.
His response was immediate. “Keep your arms up,” he commanded as he released the grip of his left hand to begin playing with my left nipple. This was spiraling out of control. Chuck didn’t mind me playing discretely with my FWBs, but I was pretty confident he wouldn’t feel the same way about what his son was doing. But I also felt powerless to stop him. He knew the secret to getting into my panties, if I had been wearing any, and I didn’t doubt he was going to discover in short order that I was going commando.
I breathlessly attempted to tell him to stop, but I was still grinding my ass against him. I was pretty sure he didn’t think I was making an honest attempt to get him to stop. Even if I was, I could feel is cock growing and given that Tommy had definitely left me wanting more in that department, I knew I was powerless to stop him. When his right hand slid down my body and began lifting up the hem of the dress, I moaned. This time it wasn’t soft and within seconds the tip of her fingers found my naughty secret.
“Do you always go out to meet your friends without panties?” he asked with a chucking tone.
I threw my head back against his chest. “This friend, yes” I replied. Jimmy responded by pushing two fingers inside my pussy.
“Dad told me he fingered you to orgasm in the front door of the gym. Is that true?”
I was pushing back against him with more force trying to convince him to whip out his cock.
“Yes,” I managed to reply. “I have a big clit and my nipples are very sensitive.” Why did I just tell him that?
His response was to pull his fingers out of my pussy and bring them back up to my breast. He then pinched both my nipples very firmly.
“These nipples?” he questioned with a condescending tone. The pain shot down my body, but swelled my clit. I started to lower my arms involuntarily, but he grabbed them and stretched them out above my head again.
“I said keep your arms above your head,” he reminded me. My mind flashed back to Tommy giving me orders in the limo. Jimmy pinched my nipples several additional times before reminding me he had asked a question. I had to think back to what he asked. It wasn’t easy as my mind was definitely not on conversation, but finally I remembered.
“Yes, these nipples, sir,” I replied. Damn, that was the second time today I called a guy sir without knowing why.
Jimmy responded by once again sliding his right hand under my dress. This time instead of sliding a finger or two inside of me, he found my clit. He rubbed me gently at first while he continued to tease my nipples. Then he increased the speed of both his fingers. I was worried he was going to bring me off while he had me pressed against the wall. Obviously I craved another orgasm, but I hated to think he was going to be the guy to give it to me. Just then my phone rang. Jimmy was gracious enough to stop playing with me while I answered. I assume he was concerned it might be his father. Instead it was Brian calling to see when I would arrive. I made up an excuse that I had been distracted, but would be leaving soon. He seemed to buy that excuse.
Jimmy said, “Hand me your phone and get on your knees.”
I knew I shouldn’t do it, but my mind and pussy flashed back to Tommy in the limo. I spun around to face Jimmy and knelt in front of him. I then handed him my phone.
“Hands behind your back,” was his next command, easily achieved while he unzipped his pants. To say his cock was a beautiful specimen would be an understatement. It’s fair to say it might have been the longest cock I’d ever seen. Maybe it was the longest I’d ever had, but it was definitely the widest. I couldn’t resist licking my lips in anticipation. There was no doubt this encounter was wrong on every level. Every level except one, I told myself. And that level was how amazing his cock was going to feel in my pussy. Or my cunt. Thinking back to Tommy had me thinking perhaps I should use that term as whatever this was, it certainly wasn’t a relationship.
Jimmy was already fairly erect from having me grind on him while he felt me up. But that didn’t stop me from taking him in my mouth to help him get all the way there. He felt wonderful in my mouth and any concerns I had about this being wrong vanished the moment the crown on his cock passed my lips. My only real question was whether he intended to have me blow him until he came or whether it intended to fuck me. Obviously that was my preference, but having him in charge even if it meant only sucking his cock was also exciting. When he pulled out of my mouth a couple minutes later, I thought for sure he was ready to fuck me. Instead he held my phone in front of my face.
“Amazing,” he said. “Even with a look of pure lust on your face, your phone still unlocks. You must look this way often.” That was followed by an evil chuckle. “Get back to work.”
I wouldn’t call it work, but I gladly took him back into my mouth. At that same time, I heard the chirp of a Facetime call attempting to connect. Then I heard Brian’s voice. “What’s up babe?” he asked.
“Hi Brian,” was Jimmy’s cheerful response. “I just wanted you to see why Alexis is delayed. She’ll be on her way over to you in a little while.”
I was focused on the cock in front of me, but I was sure Jimmy was holding my phone above my head so Brian could watch. In fact, I assume Jimmy was going to give me a facial. I’m pretty sure Brian wouldn’t mind, but you never know. In fact, maybe it would excite him. Jimmy left the call open for about a minute. Then I heard him say, “I’ll have her call you back.” That surprised me, but I was in no position to argue. Then he pulled his cock back out of my mouth, stepped back about 8 inches and then began wagging it back and forth in front of me.
“I know how much you love cock, trophy slut,” he said as if pronouncing sentence on me. Then he started stroking it. I had the distinct thought I was about to get blasted. Instead he said, “I’ll give you a choice. You can have my cum on your face and then head over to Brian’s or you can bend over the couch and I’ll fuck you.”
“What kind of choice is that?” I responded. “Do you think I’ll turn down getting fucked?”
“Unless Brian is hung like a horse, when I am done with you, he’s not going to satisfy you,” was the cocky reply.
Brian didn’t have a huge cock. He was decidedly average. But he had a good tongue and always made me cum before he fucked me. I did pause as if I was actually thinking about my options. But my mind was made up.
“After you fuck me, will you still cum on my face?” I asked. I was on the pill, but I didn’t want him to creampie me. Actually I loved getting facials was the real reason I asked.
“I’ll cum in your face for the first spurt. After that, I’m cumming in your hair and you’re going to let it dry there for Brian to see.” was his counter offer.
I wasn’t thrilled about that, but at that moment, I would have agreed to almost anything.
“Fine,” I acquiesced and then started to get up. Jimmy replied by slapping his cock in my face. “Pets stay on the floor and crawl,” he said pointing toward the living room.
Every time he pushed me further I should have said enough is enough and stood up for myself. But every time I felt my pussy gush a bit. Jimmy was clearly better at the game than Tommy. And Tommy was pretty good. Jimmy walked behind me looking at my ass as I crawled to the living room, and then, at his instruction, stood briefly to bend over the arm of the couch. This time he let me have my arms in front of me for stability. As he pushed his cock into my needy pussy and quickly started pounding me, I realized this was to help me push back against him, something I gladly did. I also quickly discovered that being bent over the arm of the couch meant my clit would rub against it. That was a very happy surprise. And it wasn’t long before I was on the edge of a major league climax. Then he stopped. I turned my head to look at him and he was smiling. He then handed me my phone.
“Facetime with Brian again,” he said. “I want him to see you cum.”
I didn’t delay hitting the buttons. Jimmy cock was buried deep inside of me, but it wasn’t moving. We needed that to happen again and quickly.
“Hi Brian,” I said when he answered. Jimmy started fucking me again, although it was a bit slower this time. I held the phone in front of me and the image looked like a POV porn movie.
“I think we’ll be done soon and then I’ll head over,” I said cheerfully. Jimmy started fucking me with more force. That translated to more stimulation on my clit. I was about to lose it. Jimmy didn’t say anything and all I could do was moan. Maybe a minute later I crashed over the edge into a delirious orgasm. I clamped down as hard as I could on Jimmy’s cock, but he kept pounding me and driving my clit against the cushion. My mind was spinning and my body was convulsing. I think I dropped the phone. I honestly don’t remember exactly what happened next, but at some point I felt my hair being grabbed and then a splash of hot cum on my face. No, I didn’t feel him cum in my hair like he promised, but as I tried to make myself presentable to leave for Brian’s place, I could see it drying my hair in clumps in the mirror. I’d made the walk of shame before, but never quite like this. I wanted to change my dress as it was disheveled from my being fucked in it, but Jimmy insisted that I go to Brian without changing for cleaning up. For some reason, I listened.
As I drove over to Brian’s I felt like the world’s biggest whore. Jimmy was right that when Brian fucked me, I got very little satisfaction. He didn’t seem upset when I walked in reeking of sex or having my hair stuck together with cum. Apparently someone who is a friend with benefits doesn’t worry that his side piece had already been used. Our encounter was disappointing compared to my last two. As I said already, Brian was fine as a lover. That’s why I kept him around. But with my eyes opened to new possibilities, I could see he wasn’t going to be enough to keep me satisfied. I managed a small orgasm while fingering myself while I blew him after he had fucked me for a while. I did enjoy him cumming in my mouth. I always did. But I was pretending it was Jimmy as I frigged my clit.
Brian offered me his shower, but I said I had to get home. I didn’t look any better than when I had arrived at Brian’s place, but I wanted to ride the wave of remembering Jimmy and Tommy so I hoped I wouldn’t get pulled over and have to explain myself to a police officer. I also didn’t want to have to explain why my car smelled like pussy and my fingers were soaked from masturbating while I was driving. I hoped arriving much like Jimmy had dismissed me would inspire him to fuck me again. I needed his cock. I got close to cumming a couple of times on the way home, but I couldn’t quite get over the edge. Something was missing and unfortunately I knew what it was.
The house was dark when I got home, but I hoped Jimmy had not gone out. When I got upstairs and saw a dim light from under his bedroom door I hoped he was watching TV and had not fallen asleep. I knocked softly on the door and thankfully heard him say, “Come in, slut.” Apparently he had been expecting him. I walked in, shutting the door behind me. He was watching TV. Actually he was watching porn and stroking his magnificent cock. He was laying on his bed with his dick standing at attention. My mouth watered in anticipation of blowing him again. He told me to walk over to the bed and then take my dress off. “I see you look even worse than when you left,” he said with a knowing chuckle as if he had expected me to arrive sans taking a shower. It was humiliating, but also exhilarating.
When I got next to the bed, he pointed to the floor and I dropped to my knees. His cock was at eye level and I began to reach for it. He slapped my hand. “You don’t have permission to touch my cock,” he informed me. He then asked, “How was Brian?”
I answered truthfully. “I was thinking of you while he fucked me. I didn’t cum.”
“Why are you here?” he asked.
“I need your cock,” I confessed. “I need to cum again. I masturbated on the way home, but I couldn’t climax.”
“I warned you that would happen,” he said triumphantly. “Hands behind your head.”
I quickly did as he asked, assuming he was going to face fuck me. I was 100% good with that. But that wasn’t his plan. Instead he swung around so he was sitting on the edge of his bed. His cock was mere inches from my mouth. I opened it signaling my willingness, but I didn’t lean forward to take his cock. I’d already learned not to assume anything with him. He began to lean forward, but instead of feeding me his cock, he used his fingers to grab my nipples. He pinched them firmly. I squirmed backward at the sudden pain, but he pulled me forward and I worked to regain my balance kneeling in front of him. Then he started teasing them.
“So you masturbated in the car but couldn’t cum?” he asked rhetorically. “I guess you needed my touch.”
“I wanted your cock,” I replied. “I need your cock.”
“I’m not sure you’ve earned my cock,” he said. That confused me. Nobody had ever turned down a chance to fuck me.
“I don’t understand?” I told him, although I finished the sentence with a moan as his nipple manipulation was having the intended effect.
“Don’t think you can just walk in here with your fake tits, tight ass and wet pussy and expect me to fuck you,” he told me. “You have to earn my cock.”
His nipple play was starting to make me dizzy with arousal and I wasn’t comprehending exactly what he was saying. Clearly he knew exactly what he was doing to me as he had done it before just a few hours ago and his dad had told him about the first time he did it to me as well. Besides my nipples becoming hard as rocks, my clit was swollen with need. I didn’t respond beyond another moan.
“Rub your clit,” he commanded. I didn’t have to be told twice. But when I started to touch my most pleasurable spot, he told me not to cum until he said I could. WTF? How was I supposed to keep from cumming? Then he started telling me his plans for me.
“Listen up whore,” he began. As I said before, I didn’t like derogatory names like that, but I couldn’t argue that I wasn’t one at that point. Honestly, kneeling with cum spattered hair and eyes pleading for permission to cum (I had not learned to beg for that yet) was a turn on.
“I don’t like you going around to your FWBs trying to satisfy your cunt. From now on, when I’m home from school, I will make sure you’re getting all the cock you need. When dad is home, we’ll be discreet, but when he is gone, you’re going to be my sex toy.”
Sarcastically I replied, “Is there anything else?”
His tone took a less playful air. “Yes,” he said. “I know you’re a nympho, but you are only allowed to cum when you get permission. I can tell when you break that rule. If you’re a good girl (I didn’t like that he didn’t say woman since I was older than him) you’ll be rewarded. You’ll get my cock and you’ll get to cum. If you’re bad, you’ll be punished.”
My mind was spinning with arousal. I didn’t think I could hold back my orgasm and I wasn’t too excited about finding out how he defined punishment. I tried to slow down how fast I was rubbing my clit without him noticing. But of course he did.
“Ah, my pet is trying to be good and not make herself cum,” he said condescendingly. “OK, let’s play a little game.” He gave both my nipples a firm squeeze as he said that shooting a lightning bolt of both pain and pleasure to my clit. “I’ll give you permission to cum, but the cost is you agree to the rules I have laid out and become my sex pet. Deal?”
I knew I could cum with just a few firm strokes of my clit, but I didn’t want to give him the satisfaction of thinking he had broken me. Yes I wanted his cock again. Craved it even. But did I want to become his pet in order to get it? “No deal,” I said defiantly. “I can live without your cock.”
“Fine,” he replied, calling my bluff. I started rubbing my clit harder preparing myself to cum. He responded by standing up, grabbing both my wrists and pinning them behind my head again. As a result, his cock pressed against my face and I took the opportunity to capture it in my mouth. Clearly he wasn’t happy with me as he removed one of his hands (I held my hands in place behind my head although I could have fought back) and pulled his cock out of my mouth. I could see a long string of saliva on it as he took his hand and slapped his cock against my nose and forehead. I kept my mouth open, but after three or four slaps of my face, he said, “I said you had to earn my cock.” He didn’t seem mad, but clearly he was looking for me to obey his rules.
I pulled my head back a few inches assuming as soon as I showed I understood what he was saying he would give me his cock. Instead he sat back down on his bed and moved his foot between my legs. He then began to play with my nipples again while he raised his foot against my pussy. Immediately I forgot about my desire to disobey him. In fact, I spread my legs a bit wider to increase the pressure his foot was putting on my foot and to get some friction on my clit. He really had released my inner slut in two encounters. My defiance once again became moans.
“You know the agreement,” he said confidently. “If you cum, you’re agreeing to being my pet and following my rules.”
I wanted to fight back. I really did. But with everything that had happened today and the arousal I felt right then, It was a losing effort. As I humped his foot, he began to lift his toes to give my clit more stimulation. It wasn’t a question of if I was going to cum. It was only a question of when. Worse, Jimmy knew I couldn’t hold back much longer and seemed pleased with himself. “I know you want to cum, slut,” he taunted me. “You’re a cum whore. You’ll do anything for an orgasm and to get my cock. Just think how good it feels in your mouth and stuffing your cunt.”
He wasn’t asking me a question about how much I craved his cock and his cum. He was telling me. He knew. His dad knew I was a nymphomaniac, but Jimmy had broken through my tough exterior to discover just what a wanton slut I could be if treated in the right way. I wasn’t thinking about how Charles would react if he found out I was his son’s pet. I wasn’t thinking at all. I was riding his foot and reveling in his fingertips on my nipples. My moans of pleasure were loud and I knew his foot was saturated with my juices. As hard as I had cum with Tommy, and indeed with Jimmy earlier in the day, I knew this orgasm was going to be bigger. Although I wasn’t capable of rational thought at the moment, I think my subconscious mind knew I was committing to the 18 year old stud if I came. But I couldn’t stop myself. With a flood of juices and my entire body beginning to convulse, I orgasmed. I wasn’t worried about what that meant, just that I was consumed with pleasure at a level I had not experienced before.
Jimmy was kind enough to let me ride out my climax for several minutes until my body began to come back to reality. He had released my nipples, but kept his foot between my legs. I appreciated that as I continued to slide my cunt back and forth on it, keeping the waves of post orgasm bliss going for longer than usual. When my breathing finally slowed and my conscious mind returned to reality, I looked up at him unsure of what would happen next. He smiled and told me to stroke his cock. Happily I moved my hands from behind my head and did exactly that.
His own breathing told me I wasn’t going to get fucked that night. But I couldn’t exactly complain. He reiterated that I had not earned his cock yet. I still didn’t understand what that meant, but I wasn’t about to argue. He told me if I was a good girl, maybe tomorrow he would fuck me again. Again I didn’t stop to ask questions. I was focused on making him cum. I still anticipated him face fucking me to get himself off, but alas, he seemed happy with a handjob. I thought back to him watching porn when I first entered the room, so maybe he had been about to cum before he started playing with me. Whatever the reason, this time instead of cumming in my hair, he mostly came on my tits. There was a bit of dribble on my hands and the end of his cock, so I scooped it up and licked it. I’d never had a man complain about that. In fact, every man I’d ever been with expected me to clean his cock after he shoots a load. But Jimmy didn’t. Apparently I had not earned that either. He did have final instructions for the night. Hopefully following them meant I was a good girl.
The basic gist of his dismissal of me for the night was to let his cum dry on my tits. It would be uncomfortable, but it would remind me of him so I was fine with that. Second, he told me he had to leave for work by 8:30 in the morning. I was to wake him at 7am with a blowjob. I was to shower and come into his room wearing just a robe. He didn’t promise to fuck me, but in my mind, I heard that pleasing him in this way made me a good girl. He did say by 7:30 he would be in the shower and that I would be making breakfast. His final instruction was that I needed to work on my orgasm control. I didn’t like the sound of that.
“Tonight, set your alarm every two hours. Starting now, I want you to masturbate until you are about to cum, and then stop. It shouldn’t take too long given your last climax. You may use any method you choose. If you orgasm, I will be able to tell and then instead of your reward in the morning, I will punish you. When the alarm goes off, do it again. You should get four rounds in tonight. If you wake up more often or can’t sleep, feel free to do it more often. Now go to your room.”
He didn’t give any other details as to how he would know or what the punishment might entail. I kind of liked that it was up to me to choose how to pleasure myself and to wonder how he would know if I came. I did wonder if I would sleep at all. I didn’t have anything on my schedule tomorrow so I figured I could take a nap after Jimmy went to work. Hopefully he would fuck me to sleep before he left. I smiled, stood up and turned toward the door.
Jimmy didn’t say anything as I walked out the door. Apparently he had said all he had to say. I shut his door and began walking down the hallway toward the master bedroom when I was startled by a noise as Chrstine came out of the hallway bathroom. She was dressed in sweatpants and a tank top. She probably had been out with friends. It was pretty obvious what I had been doing. I didn’t know what to say. Fortunately she did.
“You’re more like my mom than I realized,” she said. I searched for a response that wouldn’t put down her mom.
“We can talk about that tomorrow,” Christine continued. “Sleep well.”
My assumption was she had been home long enough to hear me orgasming with her brother. His cum on my chest, although she had not commented, probably meant she figured I fucked him. I mean, tonight. She wouldn’t have a way to know it was his cum in my hair. Christine worried me. She had to be upset by my playing with her brother. Even if she didn’t mind me seeing my FWB cause her dad had sanctioned it, fucking her brother was probably a bridge too far. I thought about following her into her bedroom so we could talk it through, but she had said we would talk tomorrow. She also said, “Sleep well,” which really wasn’t in the cards. Maybe she had not heard her brother commanding me to masturbate but not climax. Needless to say, tomorrow was going to be very interesting.