This is a story of how things started between Dolly and me. The series has a few stories, of which many are true while some are partially true. For context, I am a thin and a fairly tall person at 6 feet with a 6 inch pecker. I am not much of an alpha but at a few stages in my life, I did get lucky with a few women. Dolly was the one to whom I lost my virginity and this series has a lot of my experiences with her.
A virgin, I had only received blowjobs from my ex at the most. The closest I had gotten to sex before Dolly was a blowjob from my ex. Dolly is 5 feet 3 inch tall. She is a dancer and has the right curves at the right places. As an admirer of curves, it is one of these curves that attracted me – her ass. As a person I loved tall curvy women. For reference, someone like the porn star Alison Tyler. I use this reference as most people reading this would be watching porn. But Dolly was slightly different. She was shorter. She looked a little like Valerie Kay and had a body similar to her. But maybe slightly thicker. I can clearly remember that she was a 34B-26-38 as I had bought a pair of hot shorts for her that fitted her perfectly.
On the last of the first year at college, all of us decided to have one last blast before heading for a break. We had been fairly close leading up to the break. Drinks were on, the night was long and the party had started winding down. Dolly and I hadn’t spoken much during the party but towards the end, when the number of people had dwindled, I decided to reach out to her regarding an existing political issue that was going on between the girls. We decided to take a walk. And walk we did. The party was taking place in one of the buildings of the college campus and we walked a fair distance while talking about the issues that were going on. The topic moved over to more personal ones and as we spoke the attachment between us became evident. For more context, as classmates, we had been talking quite frequently but there was this unspoken tension between us – a force that wanted to pull us together but an unknown that kept us far.
We sat at an open clubhouse as she rested her shoulders on mine. We continued to talk about our relationships – of how her current long distance boyfriend had been avoiding her after he decided to move abroad for studies and of how I decided to end my previous relationship because I didn’t want to get married so young. At the time of this incident, I was 26 years old and so was she. We sat in the darkness of midnight and spoke softly. Unbeknownst to me, our fingers were intertwined.
Then there was silence. I turned to her and she raised her head and looked into my eyes. There was the most natural kiss I had had till then. It just happened, like the two of us had been wanting this intimacy. The kiss was soft and moist and we breathed harder and our hearts beat faster. Then it changed. The intimacy turned to lust as we lost all inhibitions of being outdoors and kissed wildly. My hands roamed her body and hers roamed mine. As we sat, my hands went under her t-shirt and cupped her breasts. My erection was at its hardest. My cock wanted to tear through my jeans and come out in the open. As I squeezed her breasts in my wild state, she moaned. I didn’t realize then that this would be a first of many moans that she would do for me. Our mouths ravaging at each other and our tongues licked whatever it could touch on. My hands never stopped squeezing her breasts. They were firm and just right in my hands. As I explored her body in the open darkness, her hands touched my jeans crotch. To say that I had been yearning for it would be an understatement. The material wasn’t the softest so however much she tried, I was only getting teased. Nevertheless, she continued to rub through my jeans and I ravished her lips and neck. After a while of this, we broke our kiss and looked into each other’s eyes.
“Shall we take a walk?” she asked
“With this?” I pointed at my erection
We laughed and started walking around the campus talking about things under the sun. The problem with me, and I don’t know if that’s the case with other men, is that this felt like a tease. There was no conclusion to what just happened. My head didn’t want to ruin what had started while my balls wanted an ending. We reached a garden and I could see the sun was about to come up. I held her hand and turned her towards me. We began kissing again.
Wet
Sloppy
As we kept kissing I gently pushed her down and to my surprise I faced no resistance. This was another wonderful thing about her. She was open to giving it a shot whatever it was without resistance. Here we were at the break of dawn, lying on top of each other in an open garden of our college. As I lay on top of her, I felt this comfort with her body, an ease that made me think “she is perfect”. As we kept making out wildly, her legs wrapped around my waist and I kept rubbing my jeans covered crotch against hers. As we dry humped, we still couldn’t stop kissing. I didn’t know what this animalistic lust was but then sense hit us. I opened my eyes and told her “I think we need to make a move”. We laughed as we got up, holding hands as we walked towards her apartment. As we walked, we kept looking at each other with a longing to involve in the lust we were in a few minutes ago. She unlocked the doors and put a finger on her lips indicating me to be silent. She went inside and realized that all the bedrooms had her housemates. Her room was also occupied by her roommate Deepti. She came back and whispered “Everyone is sleeping”.
My brain had stopped working by now. I was sleepless, was coming out of a drunken slumber and I was being controlled by my balls. The only thing I could think of was to continue what I was doing. I began kissing her and noticed the sofa next to us. I slowly pushed her to the sofa. She had taken off her jeans partially and I saw her light blue panties. Did I notice any wetness? I don’t remember. But for some reason my cock had gone down. I slowly pulled her t-shirt up and squeezed her breasts from the bra. She had a beautiful body, round boobs, just that hint of fat on her stomach that I like and wide hips. She was dusky and it was so sexy to see this beautiful dusky woman open herself to me. I saw her panties and I wanted to see what they were hiding. As I knelt next to her, kneaded her breasts and kissed her neck, my hands extended the waistband of her panties and entered. A sense of elation covered me. I felt her skip a breath and my hands met with some moist thick bush.
“She definitely wasn’t expecting any action” I thought
I couldn’t stop at her bush now. I moved towards her pussy – her warm and wet pussy and inserted my middle finger into it and began moving it in and out. Before Dolly, the only other pussy I knew of was my ex’s and I had spent time fingering and tasting her. So, I wasn’t new here but I was excited. After a few strokes, I pushed my ring finger as well into her pussy and I could feel just the right tightness. She bent her right leg at the knee to open slightly wider. I had my belt unbuckled and my jeans loosened. She put her hand inside my boxers and met with my bush.
I wasn’t expecting any action either
But what I do not understand for the life of me even to this day is why my dick was limp at that time while my balls were ready to explode. I had blue balls but my dick refused to get up. She slowly stroked it and I felt it stir a little. Suddenly, we heard some noise in one of the bedrooms. We stopped what we were doing and pulled our pants up. I looked at her and then I looked at my wet fingers. We smiled at each other. There was something naughty (of course) but also something comforting. I heard more sounds and I decided to leave her house. I went back to my room and realized one of the rooms in my apartment was empty and I kicked myself. “I should have brought her here and done whatever I wanted to.”
I went into the bathroom, started some porn and jerked off. I came very hard. I aimed my cock at the toilet bowl but the fierceness of my ejaculation sent streams all over. I let out about 10-12 jets of cum while my usual is about 4-5. My knees were weak, my balls still hurt and my brain was wheeling. I decided to take a nap. By afternoon, all of us had taken our stuff and left for our homes.
Here started 4 months of agony for me. I would talk to her every day. One evening, she called me up and said she was drunk and horny. Her boyfriend was an asshole to her and had decided to breakup. So she had decided to hit a pub and got felt upon by multiple men.
“I wish you were here. I am so horny Akshay” she said
“I have been wishing for that every day since I fingered your pussy.” I replied.
“Fucking pervert. Listen, I have been thinking. Do you want to date?” she asked
“Umm, I don’t know. I just came out of a bad breakup and I don’t know if I would be able to satisfy you emotionally.” I answered
Now, I wanted to fuck her and didn’t want to lose her. I didn’t know this at that time but in the future, the more I fucked her the more I wanted to fuck her. She was a fucking drug. I echoed the thought that I wanted to fuck her. And that echo was loud. However, personality wise, she wasn’t the type I wanted to date. I am not a “fuckboi”. I didn’t want to lay a hundred different women. I wanted to lay one woman a hundred times. I didn’t enjoy courtship. I was an introverted beta male who, in the confines of the house, wanted to fuck the living shit out of his woman. She was a nice woman, a very good person in fact and an amazing person to have sex with. But I wanted my woman to be of a particular personality. There were many instances, where Dolly reminded me of myself — instances of weakness and helplessness that would allow the tide to sweep me and not be a standing rock. I didn’t want that. So I decided to reject the option to date because if I date, I wanted to marry and keep it for long term.
“But you are keen to satisfy me sexually?” she asked
“Of course”
There was a moment of silence
“Do you want to have a friends with benefits relationship?” she asked
Now, a lot of things just happened in 5 minutes. A lot of things I ever wanted in my loser life happened in those 5 minutes. I had wanted a woman to ask me out. I wanted to reject a woman when she asked me out. I wanted a fuck buddy. I wanted all these things quite high up my list and knowing myself these were very unlikely to happen to me. I wanted these because, for some fucking reason, it gave me a sense of value – a validation of worthiness. Optimistically, I felt these might happen someday. But I didn’t expect them to happen all at once, with the same woman, over one call in a span of 5 minutes.
“Are you serious? I think you are just drunk and horny” I replied
“I am all of those” she assured me.
I wanted to bring in that I was a sensible person. So I told her “Let’s discuss this in the morning. I don’t want you to get into something that you might regret. Let’s talk about it when you are sober tomorrow morning.”
“I know what I am saying, Akshay” she replied curtly.
“That is absolutely perfect. So then you’ll say this tomorrow as well. But why are you horny? I thought you would be quite unhappy after your fight with him.”
“I came out for a party with my friend. I am just a little drunk but on the dance floor, Akshara, her boyfriend and I were dancing. It was a little crowded and I had a few men touch me” she answered
My cock twitched. The thought of her sexy body being touched by another man, no — other men. It just hit me, twitched my cock and blazed through as a thought.
I laughed “Of course, I would have cupped a feel if I saw you as well.”
“Oh shut up Akshay.” she retorted
“I was joking. But did her boyfriend feel you up?” I asked her
“When we danced, he did briefly. Akshara had gotten shots and while she was pouring them down her throat, her boyfriend decided to get extra close, put his hands on my ass, pull me towards him and pour it down my throat. I had never seen him get that close to me.” She answered
“That’s hot. Did he do anything else?” I asked out of curiosity
“Are you crazy? Akshara would go nuts. But would you touch me inappropriately, if I wanted you to?” she softly asked
“Of course. It goes without saying.”
We ended our conversation that night. Next morning, I spoke to her and asked if she remembered our discussion. She replied in affirmative and asked if I wanted to continue the FWB relationship. Now, I wanted it. I accepted it and we were now officially fuck buddies. We had numerous talks about sex and the people she had slept with. I lied that I had slept with a couple of women as part of a one night stand. I didn’t want to be sounding like a loser. We send each other nudes. Well she shared some topless photos and those of her hairy pussy while I shared dick pics and short clips of me jerking off.
“Tell me some of your fantasies” she said one day
“What fantasies?” I asked. Truth is, I wanted to take it off my mind. I wanted to tell her all the dirty things I wanted to do to her but I didn’t have an outlet to. All the while I kept saying “the things I would do to you”.
“The things you want to do… to me or with me”
“I would tell you but you should not judge me” I replied.
“If you tell me, then there’s a good chance I’ll let you do it to me” she whispered
It does not need to be mentioned that by now, I had an erection in my living room.
“In that case, the first fantasy of mine is to cum inside you” I said testing the waters
“My ex has already done that. The bastard. So I get that men want to do that” she sounded reassuring “what next?”
Sensing her cooperation there, I decided to push it higher “I have this kinky thought of watching porn and acting that out with the woman I am with. Would you be up for that?”
“I heard men in porn last really long. Would we end ours early?” she laughed
“Then we’ll do round 2” I retorted
“Somebody sounds confident” she chided “what else?”
“What do you want to do?” I decided to ask
“Ajay, my current but soon to be ex fingered me in a pub while we were sitting and having our drinks. And this was near the bartender. Fuck that was hot.”
That was hot. So I gathered she was used to a kinky perv.
“Did you cum?” I asked
“No, I was both horny and scared so I didn’t know what to do. But we got up from there and went to the beach. We made out on the sands and he continued to finger me. I should have cum then but we heard people come and so we had to stop.” She ended “but maybe sex on the beach.”
“The classic” I said
“Come on, tell me more of what you want” she asked
Slowly my cock started controlling my mind. “I like the fact that you wear skirts and dresses. Every time you wear them, I have this urge to bend you over and take you bareback from behind, preferably in public. But, I am getting ahead of myself. I wanted to try three things with you.”
“Three things? Is that it? Tell me”
“Yes. The first is at a movie theater. I want you to take off your panties and jerk me off with it. Make sure I come on the part that touches your pussy.”
“Uh-huh, and?”
“I want you to wear it again with my cum touching your pussy.”
“Ok…”
“I want to rub your pussy through your panty”
“Why? Didn’t you cum?”
“I want to smear my cum all over your pussy and rub you in a public place and make you cum so that for the rest of the day, you’ll walk around wearing your panty soaked with our cum.”
“Fuck, that is hot and dirty… and dangerous.”
“It gives me this sense of making you mine”
“I’ll need to take a pill after this” she whispered
“So does that mean you are game, then?” I asked hopefully
“We’ll see.”
“Are you touching yourself?” I asked
“Why do you want to know?”
“So that I know you are interested. The next time we go for a movie, maybe we could try it.” I suggested
We were whispering now. If it wasn’t for the distance, we would have been at it.
“What else do you want to do to me?” she asked
“The second thing and maybe it should have been the first. I love the way your ass moves. Whether you wear jeans or skirts or anything, your ass is so inviting. I want to fuck your ass. I want to ravish it and cum in it.”
“Are you saying you have to have anal sex?” she asked. Her voice was almost squealing.
I affirmed
“I’ve never had anal sex. I am a virgin there.” She confessed. That did turn me on. To fuck that beautiful ass would have been heavenly. “I’ll need to think about doing that. I have heard from some of my friends that it is painful. And it is not that you have a small dick.”
That was an ego boost.
“Do you like my dick? Or do you like bigger dicks?” I asked. As men we always have this thought of having the biggest dicks
“I think yours is fine.” She assured me.
I hoped “fine” meant that she liked it
“I like it.” She finished “Now tell me, what is the third thing you want to do… to me?”
There was something about the way she said “to me”.
“I want to have a threesome.” I said
“That is an obvious one! What is with men and threesomes. Every person I speak with, my ex, my friends, tells me they want a threesome. Most men can’t satisfy one woman but they want two at a time.” She said
“I want two men to fuck you” I replied
She was silent for a moment.
“What? Are you gay or bi? Do you want to do things to another man?” she quizzed
“I can assure you I am neither. I want to share you with another man. The thought of watching another man fucking you turns me on.”
“Fuck. I didn’t expect that. So are you talking full penetration, cumming and all of that?” she enquired
“Yes all of that” I confirmed
“I have usually found men getting angry if another man looks at their woman. But you want another man to fuck me?” she asked
“Yes, I do. That is my fantasy. Sorry if that is creepy.”
“No no, I mean I asked you and you have told me honestly. So I appreciate that. It is both hot and strange. I’ve heard girls talk about it but I’ve never expected that to happen in real life so I didn’t think of it”
“Maybe, not a lot of men have this but some do. And to be honest, it is a fantasy. I don’t know if I’ll like it in real life” I confessed.
“Mm hmm” she replied.
“Are you touching yourself?” I asked curiously
“Maybe, but why do you want to know? Does it turn you on to know that I might be considering your dirty fantasies? But I still don’t understand why you would want to share me” her curiosity was increasing.
“I don’t know, honestly. Maybe, I get a kick in knowing that other men like my woman. Maybe, I get a kick in knowing that they know how hot she is and how fuckable she is and get jealous that I get to keep her. I don’t know. Maybe it’s a validation like that.”
“Do you think I am fuckable?” she asked
“Of course you are. There’s something about you that would make men want to breed you, something animalistic. Am I the only person who finds you fuckable? Haven’t you been approached by others?”
“Breed me? That’s a vulgar and dirty phrase. I think I like it. Actually, I had an acquaintance get in touch with me during a party. She asked me if I wanted to have a threesome with her and her husband.”
“What?” I exclaimed
“I know right? Yeah that happened but I didn’t accept the invite.”
“Why?” I asked
“I didn’t like the girl or the guy” she replied.
“Do you want to try women?” I asked
“I am curious. I might be bi. I don’t know. But I like men and having sex with a man. Maybe I might try another woman as well. Who knows, I might share you with another woman too”
“Is there something your exes liked to do often with you?” I asked
“My first one liked to cum in me often and it was the worst, with the pills and all that. But my second ex, he likes to cum in my mouth.”
I was surprised. Here I was, talking to a dream woman. “What? Do you swallow? I don’t know if there are many women who do. And do you like it?”
“Yes, quite often. But it depends on the taste. Sometimes it is fine, a little salty but sometimes it isn’t. It burns a little when I swallow. Maybe it’s the diet.” She answered
I was excited beyond measure and so was my dick. I couldn’t stop jerking off after talking to her. This girl was physically hot, she was horny, she never rebuked my kinks and she swallows. It was crazy.
As I cleaned up after jerking off and hit the bed, I saw a message.
“Maybe I’ll lose my virginity to you.” The message said
“Maybe you will” I replied and went to bed.
One night, a few days later, she sent me a message “I am going to meet Vikas tomorrow. So I might not be reachable for a good part of the day.”
“Who the fuck was Vikas?” I wondered and rang her up.
“I knew you would call me up” she laughed as she picked up the phone
“So who is this guy? Do you have another fuck buddy?” I jokingly asked
“Are we exclusive now?” she asked
My heart sank. “Umm no, I guess” I spoke softly.
“It is something that started a while ago. Vikas is my ex’s best friend. He is in the merchant navy and comes to the mainland after six months. He arrived a couple of days back.” She said. We both knew she was teasing.
“Maybe more context?” I enquired
“He and I had been doing some flirting a few months ago. He told me that he wanted to have sex with me for the longest time. We met during coaching classes. I didn’t find him ugly but since I was dating his best friend, I didn’t want to cheat. Then he went on ship.”
“So it’s a one-time thing?” I asked
“Akshay, we are exclusive fuck buddies, you and I. This is something that had been pending.”
“Ok…”
“Maybe we can see if it is really your fantasy or not, you know the sharing me thing” she quipped
My cock twitched. “But I want to see it every time it happens in my fantasy.”
“If you ask me, I could tell you” she answered
“In detail?”
“Maybe”
“In detail?” I pressed
“Yes. Now good night. I have to meet him in the morning. Bye”
“Bye” I ended the call.
The next day, I didn’t receive a single message from her. I had this strange sensation of worry, anger and excitement. I was turned on. But not receiving a single message from her was frustrating. By late afternoon or early evening, I dropped her a couple of messages to ask if she was home but I didn’t receive any responses. I just hoped I wouldn’t lose someone so sexually open to another person. I didn’t know if he was really good in bed. I kept thinking, if he was such a confident guy to invite her for sex, he must be good at it. I was frustrated but I kept getting these images of a random person pounding her on a bed as she moaned. I couldn’t get that thought out. It frustrated me and turned me on. I watched a movie and decided to hit the bed a little after midnight. I checked my phone and saw a message from her. Quickly, I opened it.
“That was fun. I am so tired but it was hot. Ttyl gn”