“Brent?” I had Helen in the phone’s address book, so I knew it was her. “I’ve got a proposition for you.”
Helen was by far the wealthiest of my clients. $500 wasn’t much of anything for her, but still it surprised me when she said her proposition would pay $2000.
“Who do I have to fuck?” I asked, leery of another Paul and Lindsey situation. Although I had to admit Paul really wasn’t a bad cock sucker — even though I couldn’t bring myself to suck him — and even though Lindsey kept saying it would be hot to see me do that, it wasn’t something I wanted to do. At least once every time I went to see them, Paul would suck me hard. Lindsey giggled one time, calling him “my fluffer” when, after my second cum, I’d gone soft and wasn’t arising at all, at least until she told Paul to make me hard.
“Nobody, but you’ll need to be totally naked.” She went on to explain that she was having what she called a “Hens Sex Toy Party.” She had an acquaintance. Melissa, who did in-home lingerie and sex toy sales. She’d discussed with the woman doing it about having me there to serve drinks and perhaps to demonstrate male sex wear or sex toys. She’d said she was all for it; she always had more sales when a male model participated.
~
“Do you know who is going to be there, who is invited?” Mary asked, that next Saturday when I told her I’d agreed to do a naked modeling gig. We were lying naked on her bed, where she’d been slowly sucking my cock to get me hard so we could do it again. Mary was kind of funny that way, sometimes she would suck me off because she wanted to and liked to, but most of the time she sucked me hard just so we could fuck again sooner. Although our verbal agreement was $250 and two orgasms, most of the time I gave her much more. During the week on the days when I actually worked on her yard (I still did that — at least when other customers weren’t taking my time,) she didn’t offer to pay and I didn’t bother to ask for pay, so she was only really paying me for Saturday mornings.
“I’ve got no idea; Helen didn’t say anything about who will be there.”
“I got an invitation for the party, but I hadn’t been thinking of going. I don’t have anyone special to entice with lingerie, and I’m already having my sex needs taken care of quite nicely,” she giggled, her hand gripping and slowly stroking my cock, “but if you’re going to be performing, perhaps I will. What do you think, would you like me to get some new sexy lingerie?” Despite that she was paying me every Saturday for sex and didn’t have to seduce me, she was often dressed in sexy things when I arrived. She’d said it made her feel younger and sexy again, although I always told her that wasn’t a problem — I thought she was already quite sexy.
“You’re sexy enough even with nothing on,” I said, reaching over and tweaking a nipple. She giggled to my touch and shivered a bit.
“Go ahead, say it… “for an old lady.”
I shook my head no. “Not just for an old lady. I think you’re pretty sexy for any age.”
“Hmmph,” she disagreed, but dropped it. “Do you know who Helen knows? If she’s invited me, what if she invites your mother? I’m pretty sure she knows your mom. Does Helen even know what your real name is?”
“She calls me Brent,” I said, shaking my head no, “I’ve never given her any other name. I know when I asked who was going to be there, she said that Mitzi and Sharon and Lindsey had all said they would be, but other than that I’ve got no idea.” I thought back on those women that Mary had introduced me to and who had then introduced me to other women. I thought about what Mary said, there were so many women in town that I knew through my parents, and I’d rapidly found out that many of them were horny and lonely.
“You’ll need to wear a mask then, just in case there is someone there who knows you as Danny and you won’t need to make explanations.”
~
Helen had me standing naked to greet the women as they came to the door. I was holding a platter of drinks, Pina Colada’s, Tequila Sunrise’s, and Strawberry Margaritas, all of which were premixed in the kitchen. A platter of wines was on the entry table next to me where I was greeting; probably half the women took wine, the other half went for the mixed drinks. The responses of the women as they came in the door and saw me were almost all the same; mouths falling open, eyes dropping to my junk, and then an “Oh my!” or an “Oh My God”, followed by exclamations of “This is going to be fun!” or, “I wasn’t expecting this!” or, from one woman whose eyes lit up and her hand reached over to squeeze my cock, “Oh La La!” with an “Oh Helen! You’ve outdone yourself this time!”
Even though I was naked, I didn’t yet have an erection; actually, I was a bit nervous “performing” in front of all these women. I’d been dressed when we’d been getting ready, and when Helen sent the catering staff away and told me to get naked, I asked what would happen if I got an erection. “Well I should hope you will, that’s what we all really want to see anyway,” she said as she double checked that my mask was on and fit properly. It covered my face and nose and when I looked into the mirror, I would have had a hard time recognizing myself. “I expect that most everyone will cop a feel of that gorgeous cock or ass of yours, but that’s all I’m paying for.”
Mitzi, Mary, Sharon, Helen, and Lindsey all knew me, of course, but Helen had told them they weren’t to let others know that they knew me before this party. If someone wanted to know how to get in touch with me, they should tell them to ask Helen.
I was surprised by how many women I did know. Besides the five that were now part of my regular customers, there were several others that I knew. One woman I recognized as a neighbor of my parents. Another was Sally Gangwitch, “Ms. Gangwitch” to me when she’d been my 12th grade history teacher, who I must admit I always thought of as very pretty. Of course, since I was 18 at that time, Iwas mose interested in the girls in my class than to an older woman mo matterchow pretty she was, but i’d always, noticed the smoldering look in her eyes, as she looked at me, that said she would love to have me in her bed. She came in with another woman whose name I didn’t remember but I did know she was the high school librarian. Besides my customers, there were easily a dozen women that I knew, another dozen that I didn’t. Luckily, Helen had suggested that I just remain mute for the party and not talk at all. Even with my face covered, someone might not recognize me physically, but they might recognize my voice. When I saw so many women that I knew might possibly recognize me, I was quite glad she’d suggested that I keep my mouth shut.
The “Lingerie and More” hostess, Mellissa, had set up her table of toys and sexy wear next to the pool, so that most everyone was in the shade under the patio. When it appeared that everyone had arrived, Helen just told me to circulate and offer drinks or refills.
Most all the women were what I would call middle aged — probably 35 to 55, with a couple of women that I guessed were in the 25-35 range, with Mary and one other who were easily in their sixties.
I listened but didn’t answer to many comments, just nodding whenever anyone addressed me. Most of the time the women were talking to each other as if I weren’t there.
“God, he’s got a nice cock. Dan was like that when we got married. Now I don’t think he can even see his cock under his belly. What I wouldn’t give to take that home with me for a night.”
“And look at that ass! Where do you suppose he works out? I’d start going to a gym just to ogle him.”
“Gorgeous, isn’t it? Do you suppose we’ll get to see him hard?”
“I don’t know, but I hope so. Maybe we’ll have to help him up….” They both laughed.
All these comments were going on around me, and although none were directed at me, it didn’t keep me from overhearing them. Even though I had been seduced by Mary and had now fucked more than a dozen women, it certainly didn’t hurt my ego to realize that so many found me attractive. It wasn’t an attitude that I’d had in high school, and hearing those words now, even if not directed to me, wasn’t hard to take.
The touching began almost immediately. The first time I jumped. I’d walked up with a tray of drinks and refills and as I bent forward to lower the tray, the woman behind me slipped a hand onto my bottom, and then gave it a swat. “My God, that’s a hard ass,” I heard her say, and immediately felt another hand caress my butt.
“Yes, it is,” I heard as I turned toward the hand on my bottom. She didn’t pull her hand back, instead letting it slide across my hip and onto my cock, momentarily caressing me. “But it’s not all hard… yet.”
Once one woman had touched me, it opened the flood gates for everyone else. Most everyone had drinks already, so not many drinks were being accepted, but every chair I walked by had hands coming up to stroke my body, especially my butt and cock. Sometimes my legs and thighs, sometimes my belly and chest, but most often my butt and cock. Although my cock had swollen a bit, I wasn’t yet erect, but Mary soon took care of that.
I’d just walked by Mary when I felt her hand on my hip. Spinning me to face her, her other hand came up, grabbed my cock, and pulled me to her face. She slid me into her mouth and sucked me in. A shriek of laughter by her seated neighbor along with an “Oh my God, Mary! I didn’t think you’d actually do it!”
“Told ya!” Mary laughed, pulling away, her face looking up at me with a wink. Her mouth had finally done the job, fulfilling the wish of so many that I’d overheard, as I now had an erection.
“Yummy!” her shrieky neighbor said, and pulling me a foot towards her, leaned in and also sucked my cock into her mouth. The ice broken, from that time on virtually every hand was gripping and stroking my cock, or pulling me into their mouth, repeating what Mary had started.
I hadn’t seen Helen for a few moments. Glancing around, I found her at the door into the house, talking with my mother’s good friend Martha. My eyes opened wide in shock at seeing her, and my one-time fantasy girl Robin, standing beside her, looking my way. Another girl I recognized as a former cheerleader friend of Robin’s, whose name I didn’t know, was standing beside them. Helen was the only one not currently looking at me as she was speaking to Martha. But, as Martha said something, even Helen turned to look at me as the woman I was standing in front of was busily sucking my cock.
How many times had I ever dreamed of being naked with Robin? Of Robin sucking my cock, of fondling her exquisite breasts? I immediately wondered if Robin, or her mother, had recognized me, but I saw no indication of that having happened.
At long last the tray of drinks I was carrying around had nearly emptied, and I slowly headed toward the kitchen for refills. On the way I was stopped by just about every woman I came near. Most of them were eager to give my cock a quick suck, my balls a quick fondle, or my butt a quick squeeze, invariably with innumerable comments about a “hard ass” or a “hard body” or “what a cock!” Slipping into the kitchen I reloaded the tray with a variety of drinks, all in clear “plastic” crystal as we were around the pool, and headed out again. No sooner had I stepped out than Helen’s “Brent!” call, and a beckoning hand, directed me to come over to her. If they didn’t know before, now everyone knew I was Brent.
“Oh my, Helen, you’ve outdone yourself this time,” Martha said, taking a Strawberry Margarita with her left hand and reaching for my erection with her right. “Why don’t you bring this big boy back by when I’m seated so I can take a sample?” she laughed, turning her attention to me.
“Mother!” Robin laughed and playfully swatted her mother’s hand away from my cock, only to reach down and caress me herself.
“What?” Her mother said in feigned surprise, “That’s what he’s here for, isn’t that right, Helen?”
“Yeah but I think this one’s for me,” Robin said, her hand now wrapped around my cock, “he’s much too young for you.” Keeping my self-imposed silence, I realized this was the exact reason I hadn’t said anything the entire party. If there was anyone, including those newly arrived, who were to recognize me, it just might be Martha or Robin. I said nothing, turning the tray toward her friend who, instead of reaching for a glass, just reached for my cock. “Not too young for me, either,” she said, pushing Robin’s hand away and wrapping her own fingers around me.
My hand had moved the tray toward her friend, but my eyes had stopped on Robin. Something about her eye had arrested my sweep of her face and I realized she had makeup hiding a black eye. My eyes locked on her face just momentarily, and then as I turned away a dark spot on her arm, in the shape of fingers, also covered in makeup, caught my eye. “You be sure and come by and see us again!” the friend said with a giggle.
Robin and her friend started walking away, but her mother said, “Brent?” a question in her voice. “Are you the Brent that Mitzi was telling me about?” I smiled and nodded. “I think I’m going to need his phone number before I leave, Helen,” she said. Turning I just walked away, hearing Helen and Martha speaking but not clearly enough to hear what was said.
I continued my rounds and, although I still had women touching and fondling and taking me in their mouths, it was Robin that my mind was on. Robin, my long-time fantasy girl, had fondled my cock and didn’t have any idea who I was. Robin, now seated next to her friend, chatting and, with both looking my way, I knew their chat was about me. I couldn’t ignore them, and as their glasses became empty, I slowly worked my way across the patio toward them. The tray empty again, I returned and refilled, returning their direction just a few moments later.
There were several women seated between where I was and Robin, including one woman that I didn’t know but who was quite memorable in that she had to have the largest breasts that I’d ever seen. A short thing, if anything, she would barely have been 5 feet tall. The shirt she was wearing was cleavage baring, and she had a tremendous amount of that showing. As large as her breasts were, and as much breast flesh as was exposed, I knew her nipples could only have been barely covered. “Hey Trisha,” she said to her neighboring friend as I offered the tray of drinks, her hand coming out to grip my cock just like most of the other women, “do you know what the best part of a hard cock is?”
Trisha laughed, “I don’t know Gigi, you tell me. What’s the best part of a hard cock?”
“This,” she said, releasing my cock momentarily, gripping the deep U of her shirt and pulling down, her mammoth breasts spilling free. Her hand rose back and gripped my cock, pulling me to her. I stumbled and caught myself with one hand on her bare shoulder, almost spilling the, thankfully, almost empty tray of drinks as she guided my cock between her breasts. She released me with her hand and pressed both breasts around my cock. “Hard cocks always love to fuck my titties,” she laughed.
“Gigi, you’re such a slut! Put your girls away and leave some for the rest of us,” Trisha said, reaching over towards her breasts to pull my cock free. Pushing back, I straightened up, Trisha’s hand on my cock, pulling me towards her. “Nobody’s getting anything more than just a taste anyway,” she said, leaning forward just that little bit more to lick my cock, and momentarily suck the head into her mouth.
“Party pooper,” Gigi laughed, slipping her bra and shirt back up around her mammoth breasts. “Come back and see me if you need some relief,” she said to me, as she reached up and snatched the last Tequila Sunrise from the tray.
I moved on, offering the partially empty tray of drinks to Robin and her friend. They took the last two Strawberry Margarita’s leaving the tray almost totally empty again. Robin looked up at me, paused, and said “Do I know you?”
Was there something about me that she recognized? I could feel my pulse beating in my temples; I suspect my blood pressure went through the roof, and I just hoped I didn’t blush. I just shrugged my shoulders, giving a mute response. “There’s something about you…” she said.
Shifting her drink to her left hand she reached up and grabbed my cock, just as nearly every other woman had. “Umm, I don’t know, I think I would have remembered this,” she said, leaning forward a bit and taking me into her mouth momentarily. “What do you think, Lori, have you ever tasted this one?” She moved out of the way, pushing my cock toward Lori, who unlike any other woman there, didn’t just take me in her mouth as a tease, but began pumping her mouth up and down on me. Her hands reached around and gripped my ass, holding me in place as she not just sucked but fucked my cock with her mouth.
“Whoo Hoo!” I heard a catcall from a few seats over, followed by several laughs and a “You go girl!” and another voice “God, I wish I’d done that!” followed by more laughs.
I tried to pull back but with her fingernails in my ass, I wasn’t getting away much until I heard Helen’s voice, “Ok, girls, fun is fun, but that’s not what he’s here for. Come with me, Brent.”
~
I followed Helen into the pool changing room, just off the patio. She introduced me to the woman who was running this sex toy and lingerie party, Melissa. I had seen her from across the patio several times while I was ‘entertaining’, and my assessment from afar wasn’t nearly good enough. Melissa was… delectable? Older than me, but younger than any woman I’d ever been with. A cute face, gorgeous hair, and a body to die for. Except that I was naked and already had a boner, I knew if I’d been introduced to her in other circumstances Petey would have been acting up at the thought of her.
Melissa had everything laid out that she wanted me to wear and model for the ladies on a table, in order. When I came in, all I had to do was change into the next item, come out when she indicated, and then walk around and let the ladies ‘feel the fit’, as much as I saw fit to do. Although the majority of the items were sexy women’s lingerie, baby dolls, open cup bras, silky slinky night wear and sex toys, modeling of the “men’s wear” was a definite hit. Melissa later reiterated what Helen had told me when she recruited me, that she always sold more stuff for women to take home to their husbands when she had a male model to help.
~
“Well?” Helen said when I, once again clothed, had helped Melissa load her display items back into her car and leave. “What do you think? How did it go?”
“Not quite what I expected, but then again I wasn’t sure quite what to expect.”
“You did a great job. Were there any problems?”
“I thought that Robin’s friend Lori was going to suck me off, right until you interrupted. She didn’t want to let go.”
“Yeah, it was perfect timing there.”
“And that busty woman, Gigi? She wanted me to fuck her titties, had me wrapped in there pretty good as I was off balance.”
“You mean Betty.”
I shook my head, “Her friends were calling her Gigi.”
Helen laughed. “That’s just her nickname, because of her boobs. Her real name is Betty, but because of her 32G bra size, her nickname is G-G. Gigi, for those who don’t know.” I laughed with her. “You made quite an impression; you know.” I shrugged my shoulders, not knowing what to say. “I had multiple inquiries for your phone number and several asked what you normally do. I told them I thought you were saving money for college, and they wanted to know if you did private parties.” I just nodded. “I didn’t tell them anything other than I’d ask if you wanted your phone number given out. I didn’t think you’d have a problem, but thought I’d ask you first.” I assured her I needed all the money I could save, and if anyone called, she could share my business number.
~
“Brent’s Tree Service?” the woman’s voice said after I said hello.
“Yes,” I answered, a vague feeling that I should know this voice running through my mind.
“I saw you the other day at Helen’s and she said you provide wonderful… Tree and other… maintenance… services.” Although she was sticking with the euphemism, there was no doubt in my mind about what she and I were talking about.
“I do,” I answered, “are you in need of some… yard… maintenance?”
“If you bring the tree you had with you the other day I sure am.”
“I can certainly do that. I haven’t left it home yet,” I answered and chuckled.
“Uhmm. I hope not. I’ve been thinking of that… tree… and what it could do for me ever since Helen’s… party. I’m curious, how much are your services?”
“Individual service starts at $250 per hour with a two-hour minimum, but can be extended, at least until I run out of wood.” I didn’t know whether she caught the innuendo or not; she didn’t laugh.
“Ah. And do you do clean-up? I might provide… something to eat, but I would expect the service worker to clean up from there.”
“Oh definitely, not a problem. I always clean up after I eat and leave the kitchen clean.”
“Oh good.” I could hear a bit of heavy breathing, but she was quiet for a moment.
“Would you like me to check my calendar and see if I can fit you in?”
She giggled. “I was actually hoping that I could fit you in.” It took me a second but then I realized her double entente and laughed with her.
“I will certainly give it a try.”
“And you do full service?” I hesitated for a moment, not sure what it was that she was asking more than we’d already hinted at.
“Just about anything,” I answered, “what have you got in mind?”
“Do you do front yards and… backyards?”
“I’ve never done a backyard,” I answered after a few second pause, “but we can certainly give it a try.” The request caught me by surprise — just what did I feel about back-door play? Not something I had contemplated as nobody, until now, had ever brought it up. Certainly, I’d heard of anal sex, but it wasn’t anything I’d ever been attracted to.
“I think that’s what I really need. My husband mostly takes care of the front yard, although he hasn’t given it a thorough cleaning in quite some time, I just can’t get him to do the backyard at all. I, um, I’d like you to do some cleanup in front and, uh, I’d like my backyard taken care of too.”
“Ah, I see. Will your husband be at home… or assisting?” I asked, wondering if he was going to be another Paul.
“Oh no. No. He won’t know anything about this. Have you got any problem working on a yard at a different location?”
“What have you got in mind?”
“The Crowne Plaza, downtown? It’s not far from my work and I’m thinking I can take an afternoon off.” I thought she was going to say immediately, but instead we made an appointment for the following week.
~
The text just said, “Room 228.”
Nobody even gave me a second look as I strode in through the door from the parking lot and walked straight to the bank of elevators, acting like I knew where I was going. Seeing the stairway just beyond, I continued and walked up the stairs, making the U-turn and hearing the “ding” of an arriving elevator at the ground floor just as I reached the second floor. Signs directed me to room 228, and I rapped on the door.
“Who is it?” The voice called out from within.
“Brent’s Tree… and Room Service” I changed my response with an inward chuckle.
The door swung inward, and I stopped, shocked.
“Danny?” Robin’s mother, Martha, said, obviously as shocked as I was. “Oh my God, this was a mistake.”
I suppose it was bound to happen, sooner or later, that “Brent” was going to run into someone who knew Brent was really ‘Danny.’ But why did it have to be Robin’s mom?
“I thought your voice was familiar when we talked on the phone, but I didn’t realize it was you,” I said.
“Oh my God, this is so embarrassing.”
I stood there for another moment and when she didn’t move aside, I said, “Shall I come in?” Her eyes widened, I saw her swallow, and her eyes scanned down my body as she backed up, making room for me to enter the room. I don’t know how I recognized it, but in that instant realized she had made the decision that she did indeed still want to fuck me, even if she did know who I really was, even if I was her friend’s teenage son.
Martha was wearing a simple pale pink, sleeveless blouse, and grey pleated skirt. Lacy decorations on her bra were visible through her semi-translucent blouse. Although partially transparent, it was still obviously business professional attire, even with the two barely visible points of her nipples. I had to wonder whether those tiny bumps of her nipples were normally visible or whether her nipples were more erect than normal. Her bra seemed to be full coverage but with the lacy material highlighting her blouse I couldn’t help but wonder if it was perhaps a bit sexier than what a businesswoman would normally wear.
“Is it more embarrassing for you? Or for me?” I questioned. “Is it more embarrassing because you wanted to hire a stranger…” I paused momentarily, and decided to get it out in the open, “for no strings attached sex and found out he’s the son of your friend, or for me to find out that you, the friend of my mother, are willing to pay me for it?”
She stood silently for a moment; I could tell that she was second guessing herself. “It’s OK, Martha,” I said, taking another step forward to her, and reaching up two handed, fondled the collar of her blouse. I felt her recoil slightly away from me, and then she straightened up, staying where she was. “Nobody will ever know what happens in this room, whether you ask me to stay or ask me to leave.” She nervously swallowed again. “So? Which will it be? Do you want me to turn around and walk out that door? If so, no one will ever know I was here.” I gave it a second and said, “Or do you want me to stay?”
“Stay,” she whispered.
“Good choice,” I smiled, letting my fingers slide down from her collar to the top button on her silky blouse. The button easily slipped free, and taking my time I fondled the material before moving down one button. “Nice blouse,” I complimented, slipped the second button, and then ran my hands sideways to her breasts, my finger rubbing gently across the barely visible nubs of her nipples. “I’ll bet you’d look good in this without a bra.” I couldn’t tell for sure, but it looked like her nipples perked up even more to my slight caress.
“Do I… Do I need to pay you?” She stammered as my fingers found the third button.
“Normally I collect up front,” I nodded, “but I know you. It’s ok. We’ll worry about that later.” I sensed that asking her for money right now would change the dynamic, and she seemed to be somewhat reluctant to continue this, so I decided to just keep the forward motion. My hands continued down, pulling her blouse from her skirt as I reached the last visible button. Pushing the halves apart as the bottom button came free, the blouse easily slid open over her bra covered breasts, exposing them and her bare belly. I pushed the blouse aside with my wrists, gripped her waist and slid my hands up her belly to her bra and breasts, filling my hands and kneading them this time. Pushing further away from the center of her body, I used my wrists and forearms to shed her blouse.
She dropped her arms and shoulders; the blouse fell to her wrists, and I took it from her, as otherwise it would have fallen to the ground. I glanced down just long enough to ascertain how I was holding the blouse, folded it in two, and turned to step over to where I gently laid it across the arm of the chair. I stepped out of her reach as I put the blouse down and when I turned back, she hadn’t moved. As I stepped back to her, her hand now came up and stroked up and across my chest and shirt. “Do you want to take my shirt off or do you want me to?” I asked, sensing her desire.
“Uhm… I want to,” she said, finally relaxing a bit, as her fingers began fumbling with my polo shirt. She loosened the two buttons on the neck and then pulled it out of my pants. I lifted my arms as she pulled it up and off, tossing it to the same chair where I’d laid her blouse. “Oh my God, you’ve grown up!” she said, her hands running up and across my pecs, her thumbs finding and caressing my nipples.
“Happens to most of us eventually,” I answered with a smile, my hands reaching for her waist and skirt. Her hands slid down my belly until her fingers found and began fumbling with my belt. I slid my hands around her waist, past the side zipper, and gripped her ass two handed and began to pull her closer. Not feeling the edge of her underwear, I stroked her hips and ass, finding the crack of her ass, my fingers rising but still feeling nothing. I ran my hands to the bottom of her skirt, lifting my hands up underneath, and found nothing but bare flesh.
Slowly sliding my hand to her sex, I still found nothing but bare skin and a hot and wet pussy. “Why, Martha! You’re not wearing panties!” I said. She flinched as my finger found her clit and pressed against it.
“I soaked them… two hours ago,” she said as the fingers of her one hand slipped into the front of my pants and caressed my cock head while her other hand gripped my elbow and pulled me closer.
“Two hours?” I marveled, “why is that?”
“More like four hours,” she answered her fingers pulling out of my pants, her other hand coming over to grip my belt and pants to loosen them. “I was so wet I had to take them off.” My belt free, a shudder ran through her body just as her hands gripped my pants to pull them open, my finger moving across her clit the cause. A pant exuded from her mouth, her grip on my pants changing to her arms encircling me, pulling me close. Realizing she was close I wiggled my fingertip back and forth across her clit — and she almost instantly convulsed in orgasm, multiple gasps emanating from her mouth as her body shuddered.
“Nobody has touched me there except my husband since before Robin was born,” she said a moment later after I’d stilled my fingers and she’d finished convulsing. “Oh my God, I’ve wanted that all day.” I heard what she said and just filed it in my memory for the moment.
Moving my finger away from her clit I realized I found no pubic hair. I ran my hand up above her pussy and then back down, finding and slipping my fingers along her labia. Several of my customers had decoratively trimmed their pubic hair; triangles, small rectangles above their clit, or landing strips, but for the most part older women were untouched in their pubes, or just closely trimmed.
“You don’t have any hair,” I commented, running my fingers around her sex, “Did you shave?”
“Robin waxes and she convinced me I should do it too.”
“Why?”
“She said guys like to do oral more if it’s bald.”
“Uhmm,” I acknowledged, my fingers now sliding between her labia, feeling how wet and slippery she still was. “And do you want oral?”
“I told you I did. I was hoping my husband would want to, I don’t think he noticed.”
“No? Why not? How could he not notice?”
“I went with Robin when she got her Brazilian last Monday. She gets one every four or 5 weeks, and she’s been telling me I should do it to. I guess all the girls do it these days, don’t they? My husband and I haven’t had sex in about two weeks, and he hasn’t gone down on me in probably 5 years. I thought if I got it done, he might want to. I don’t even know if he noticed.”
“He didn’t notice?” I commented, “A sexy MILF like you?”
“We had sex all the time when we first got married. It’s not quite like it was anymore,” she answered as I pulled my hands from under her skirt and, finding the side zipper, lowered it. Almost simultaneously her skirt slid down over her hips and bottom. I held it and lowered it until she stepped out of it so that she was now totally naked except for her bra. I folded the skirt in two and laid it by her blouse before turning back to her. She immediately reached for my pants again, but I fended her off, instead gripping her arms and walking her backward the few steps to the bed.
When her legs hit the bed, she sat, and I pushed her backward until she lay back onto the bed. Sliding my hands down her body, over her breasts, I reached her hips as I dropped between her legs. Running my hands from her hips, I caressed the crease of her legs, the whole time observing her pussy, and especially her large, meaty labia. I slid my fingers in against her sex, squeezing her labia together, pooching them out, and imagining them protruding in a camel toe through tight fitting shorts or panties or a bikini bottom. “Very nice,” I told her, raising my eyes to hers. “I’ve never seen a hairless pussy.”
“Never?” she asked, her hips twinging to my caresses.
“Not totally,” I answered, “most older women don’t shave at all, but a few have shaved some.” Letting my fingers ease the pinch of her labia I slipped a finger down and into her vagina. “Robin waxes her pussy too?”
“Yes.” I couldn’t help myself, wondering exactly how much my fantasy girl resembled her mother.
“Because she likes oral sex?”
“All women like oral sex.”
“Is that so? And do you? Do you want me to do you with my tongue?”
“Will you shut up and eat me?”
Eating a freshly waxed pussy was totally different. No fighting pubic hair, no pubic hair coming loose and ending in my mouth. Even though I’d never seen one completely bald, I’d had several women who shaved some, and that was about like a man with a beard, it wasn’t bad with the lay of the hairs, but moving the opposite direction was slightly prickly even after being freshly shaved. With Martha, her pussy was still totally smooth. I gave her everything I knew, listening to her body, tasting her pussy, her juices, and tonguing her clit, and finding her skin still slippery smooth. I had two fingers in her vagina, her hips rising to force herself harder against my tongue, when she finally bucked and quivered, grabbing my head to hold me still.
“Oh my God!” she panted, followed by another “Oh my God!” I felt her body finally relaxing underneath me, her panting slowing down.
“I take it that was ok?” I asked, leaning forward, and tonguing her clit once more. She quivered and pushed my head away.
“Oh, you have no idea. I’ve wanted that, I’ve needed that for ages. That was really nice; that might have been worth $500 by itself.”
“I liked it too, your pussy is so smooth.”
I stood up, still between her legs. “Take your pants off,” she instructed. I’d planned on doing that anyway, but decided to tease a bit.
“Don’t you want to do it?”
“I just want to see that cock that I’ve been thinking about since Helen’s party.” I released my pants, letting them just fall to the floor, now standing naked between Martha’s legs. “He’s gorgeous. Bring that up here,” she said, gripping my cock and pulling me towards her. Moving outside her legs, I crawled onto the bed beside her, her hand immediately going back to my erection.
“Does anyone else know that “Brent” is Danny?” she asked, her hand pulling me to the bed beside her.
“Just one,” I said.
“Who’s that?”
I shook my head no. “I don’t kiss and tell, even if I don’t kiss.”
“You don’t kiss?”
“Something I started from the beginning. Kissing is about love; this is about sex.”
“Hmmm,” she responded. “You’ve got quite a reputation for making women happy, you know?” I shrugged a shoulder. Every woman that I’d been with had said something like “you come highly recommended,” or similar. I kind of assumed I was leaving women happy, but nobody had ever said that specifically.
“How does this work?” she asked. Did I understand you guarantee at least two orgasms?”
“I don’t guarantee anything,” I answered with a smile, “although generally it’s no problem to have at least two orgasms. I’m here for you, so whatever gets you off…”
“And you cum too?”
“Of course. I guess I’m about like most guys. I cum pretty fast the first time, but after that, I can usually control an orgasm until after you’ve cum. Some women cum quite fast, at least one woman likes about two hours of oral and foreplay before she cums just once. My tongue can get a little tired working on her.” I smiled, letting her know I wasn’t complaining. “So, what’s your desire, Martha?”
She didn’t answer for a moment, her hand holding, squeezing, and slowly stroking my erection. “I want you to do what my husband won’t.”
“Hmm,” I said, “your husband won’t do something for you? And what is that?” I knew what she’d hinted at with our original phone call, I’d just eaten her to a magnificent orgasm, but I wasn’t going to go there unless she asked for it.
“Will you… I want you to fuck me in the ass.” She started to ask, and changed to telling me what she wanted.
“You’ve done it before and you like it, or is it something you want to try?”
She sighed. “We all like what we like, don’t we?” I nodded. “I started doing anal before I started vaginal sex. My boyfriend wanted to fuck, I said no, and he kept pushing. My older sister was the one that told me I should let him take my ass instead. She gave me lube and condoms, and told me how to get ready, and said the trick was to push out, like I was taking a poop, when he was trying to get in. The next time when he was pushing me to fuck, I told him if he wanted, he could fuck my ass. We did it, with lots of lube it really wasn’t bad at all, actually it was quite nice. When he was fingering my clit at the same time, I had a nice orgasm. Over time I found I really liked when he fucked my ass, even after I started having vaginal sex. Normal sex was good, but the orgasms when someone was taking my behind… they could be… phenomenal. The only lover of mine who’s never done my ass is my husband.”
“You’ll have to guide me; I’ve never done it before.”
Martha just looked at me for a moment, her tongue slipping between her lips, when suddenly she shook her head and said “Fuck!”
“What?” I said, surprised at her outburst.
“What am I going to tell your Mother?”
I shook my head in surprise, thought about it calmly for a moment, and then said, “You’ll tell her nothing of course. What you do, and what I do, has nothing to do with her, any more than what you and your husband do has nothing to do with her. Like I said, there is one other woman who knows who I really am and also knows my mother. I’ve seen her once while my mother was there, and we’ll do the same thing. You’ll treat me like you’ve always treated me in public, and I’ll treat you the same. You’re just my mother’s friend whom I’m only barely acquainted with.” I slipped up onto the bed beside her, pushed her onto her back from her side, and straddled her. “But for right now,” I said, reaching up to her bra, pushing it up and over her breasts, “I want to play with your nipples.” I filled my hands with both breasts, my thumb and finger coming together to roll her nipples between them.
“Oh, you are something else,” she giggled, and sat up, forcing me back momentarily. Reaching behind herself she unhooked her bra and pulled it off until she was now as naked as I was.
I smiled at her, reaching for her breasts once again.
When she pushed me backward and off her legs, I rolled to the side, and she turned, bent her face to my crotch, and took my cock in her mouth. She bobbed and twisted, sucked, and licked, for several minutes, the tingling increasing in my cock the entire time. “I’ve always loved sucking cock,” she said when she pulled away, holding my cock upright, “but I can do that, or get fucked, at home with my husband.”
I rolled back and off the bed, grabbed my pants and pulled one of the condoms out of my pocket. “Do you want to put it on?” I asked, after I’d torn open the foil and pulled it out.
“Yeah,” she nodded, and I handed her the condom, moving my erection back up towards her face. “I haven’t needed or used a rubber since before Robin was born. Do you always use them?”
“Always,” I confirmed as she rolled it over my erection. As soon as she had the raincoat in place, she rolled away from me and off the bed, moving naked across the room to the dresser and her purse which I hadn’t really noticed before. Reaching in, she pulled out a small squeeze bottle and turned back, stepping over to the easy chair in the corner and beckoning me to join her.
She handed me the bottle. “This is lube. I would normally do it before I got this far but didn’t want to do it at work, so you need to lube my ass and your cock, and then I’ll guide you in. You have to take it easy until I get used to you, OK?” Turning, she knelt in the chair, extending her ass up and backwards toward me and dropping her arms and shoulders to the armrests. In this position her ass was naturally spread, her rosebud totally visible, her meaty labia accented between her legs. I could have easily slipped into her vagina and done her doggie style in this position but instead followed her directions.
“Just dribble it on and spread it around,” she instructed. I put several drops around her anus, rubbing up and around. “Work some in,” she said, “use your finger.” I did, pushing right on her rosebud. “Yeah, that’s it. Now push harder, work the lube inside.”
“In your ass?”
“In my ass. Lots of lube. Put your finger in as far as you can.”
I could feel her ass pushing back, pushing against my finger, and surprisingly her ass seemed to open right up, allowing my finger inside her. I wasn’t sure what to expect, but I really felt nothing. Unlike a vagina, the tension seemed only to be on the sphincter muscle; it seemed like there was a large, thankfully empty, cavity inside. “Oh My God… it’s been so long.” I wasn’t sure what to do now, slowly began working my finger back out and then moved it inward again — finger fucking her ass. “More lube, make it really slippery if you can.” I dribbled a few more drops around, and she said, “Now your thumb.”
“My thumb?”
“It’s bigger.”
“Oh.”
I did as she requested pushing my thumb in as far as I could, clear up through the base knuckle, the largest part of my thumb, eliciting a groan of satisfaction from her, until she said. “Oh… I’m ready… Add some lube to your cock and I want you in my ass.”
Making sure the end of my cock was well lubed, I pressed it against her asshole. Just as with my finger and thumb I could feel her pressing back, but my cock was easily twice as big around as my thumb. Still, I felt her ass opening to accept me, and suddenly, I popped through and into her rectum. “OH! Just hold still for a minute!” she exclaimed, “Let me get used to it. It’s been so long… you feel so big…” she panted. “Ok, slowly to start…” she added a moment or two later… “Yeah, like that. Not too deep… NOT too deep… Ok, better. You can go deeper after I get used to you. Oh My God, I haven’t had a cock in my ass in… oh my… oh… twenty-three…” she panted, “twenty-four years…” Minding her “not too deep” instruction I eased my cock into her ass, perhaps only halfway, before slowly easing back out. “More lube,” she instructed. She had been mostly on all fours, presenting her ass to me, but now lowered a shoulder to the chair, her arm snaking back underneath herself to her pussy. “Ok, I’m ready, faster now. I need to…” she shuddered; I realized her fingers had found her clit.
I didn’t need a bunch of instruction from here on. My cock was in a tight space, her sphincter gradually loosening up as I slid in and out. I started shallow but naturally began going deeper as I took up a faster fucking motion. I hadn’t expected it when her body began to quiver and shake in orgasm, her bottom pushing back toward me every time I moved into her, an “Oh… Oh… Oh…” with every thrust. The stimulation on my cock wasn’t that great, just around the shaft and barely any on my cock head at all. I could feel it, and although she wasn’t going to get me off very fast, her orgasm continued, and if anything — got stronger. Her “Oh…Oh… Oh,” turned into and “Oh fuck… OH FUCK!… OH my God!… OH Fuck…” We continued for perhaps five minutes, until her hand pulled away from her clit, reached around her hip and, her entire body still quivering, her hand reached for me, telling me to stop my movements.
I stopped moving, my cock still embedded in her ass, her quivering body quieting until I pulled back, causing another convulsion from her. I started to push back in but her “No! It’s too much!” told me to hold still. I pulled back, so my cock head was just inside her sphincter and then, after a moment or two, pulled out. “OH!” she said, this time her moan a protest, “you felt so good.” She pushed back into an upright position, onto her knees, and I moved back, allowing her to stand. She faltered, nearly falling, but I grabbed her arm, and she turned and moved toward the bed. She fell forward, and then looked back at me, seeing the condom still covering my cock. “Get rid of that thing, and come up here and hold me.”
I did as she asked and, since I hadn’t cum myself, at least for the moment I was still hard. When I returned from disposing of the condom, she was in a fetal position, and when I crawled up behind her, she pulled my arm over her shoulder and between her breasts.
I felt her slowly begin to relax and with my hand between her breasts it was easy to raise it to her breast, filling my hand, and fondling her nipple. She didn’t initially say anything.
“Oh my God,” she said, “I’d forgotten how that wears me out.”
“I take it you came?” I asked, “I could tell you liked it but couldn’t tell when you did.”
“Are you kidding? I was coming that entire time. I can come with fucking, but nothing like that. It just goes on and on and on….” She let out a long exhale. “Did you cum?”
“No.”
“Oh. Sorry.”
“No need to be sorry, this was for you.” We lay there for perhaps five minutes before she said, “Come on, let’s go take a shower.”
Rolling away and standing, she reached back for my hand. I stood and walked with her to the bathroom. “No matter how much I like that, I always feel like I need to shower and clean up afterward,” she said as she reached in and started the shower. “My butt always feels slimy until I do.”
I took the soap from her and soaped up her body, spending more time than I needed on her ample breasts, but when I slid my hands onto her bottom, she stopped me before I ran a soapy finger into the crack. “I’m going to be sore back there tomorrow but, My God, was that worth it.” She took the soap and I watched as she ran more soap suds between her ass cheeks, her own finger caressing and then rinsed thoroughly.
When I turned to step out of the shower, as she was turning it off, she said, “Give me a minute to use the toilet and I’ll be right out.” I sat on the bed; my cock having wilted slightly. I was thinking maybe I should stroke myself to get hard when after just a few moments she stepped out of the bath wearing just the pale pink blouse that she’d been wearing when I arrived at the room. Extending to her crotch, it was obvious she was totally naked beneath. I’d recognized when I first saw it that it was at least semi-translucent, the decorative lace of her bra visible where it was pressed against the material, but also that her skin had been visible where it touched. Now my attention was drawn to her nipples, no longer hidden by her bra, and deliciously displayed through the material, and her naked pussy peaking from beneath the hem.
“Didn’t think I heard you, did you?” she asked as she stepped up to me, stopping just in front of me. I remembered saying that her shirt would look good without a bra.
“Wow,” I said, reaching up to both breasts, squeezing her breasts gently through the shirt, my fingers finding and pinching down on both nipples. “As I thought, very nice without a bra. Very sexy.”
“I’m glad you think so,” she replied, as she leaned down, rested both hands on my knees, and then leaning still further took my cock into her mouth. The way she was leaning on me I had no problem slipping the buttons on her blouse once again, moving the material away and fondling her bare breasts.
“Great tits,” I said a few moments later. “This blouse is really sexy like this.”
“I’m glad,” she repeated, pulling away from my cock with her mouth, reaching for it with one hand to hold me upright. “Every woman likes to feel sexy. Have you got another condom?”
“Of course,” I replied, but was unable to retrieve it immediately as she leaned down and took just the head of my cock in her mouth again, holding me upright with one hand. Now loving on my cock with her tongue and lips, I recognized that she was well experienced in giving head. Her tongue moistened my glans before her lips slid over the rim, her tongue swirling around, tantalizing for just a few moments before she pulled back again and said, “What do you think they would say to this?”
“They who?” I responded, baffled. “To what?”
“Robin and Lori, of course,” she pulled off and answered with a giggle, immediately slipping her lips back around my cock head.
“Who’s Lori?” I puzzled aloud.
“Lori? Robin’s old cheerleading buddy? At Helen’s party, they were talking about what it would be like to do you. Do you suppose,” she giggled, “they had any idea that I would like to do you too?”
“They were saying that?” I questioned, reaching down and twiddling Martha’s nipples again. “Seems strange that they were talking that way, or at least Robin was, around her mother.”
“We’re pretty tight that way…”
“Yeah, I guess. If you went with her to wax your pussy…”
“Do you like it?”
“I do. Very sexy,” I said, sliding my hand down to finger her, playing with her labia. “I liked eating you with it naked.” She spread her legs, inviting my touch, and again took me into her mouth until she asked about another condom. It was just a moment or two later that she pulled away and said, “Why don’t you get it?”
I did, rolling off the bed to retrieve it from my pants pocket. As soon as I did, she climbed onto the bed over me, straddling my legs, and reached for the condom in my hand. “Let me,” she said, taking it, lifting my cock upright and again rolling the condom down onto my erection. As soon as she was done, she held my cock upright, rose a bit herself, and slid down onto me.
With her riding me cowgirl, my hands were free to play with her breasts, which I did. I fondled her through the blouse, rubbing her nipples through the silky material but also slipping my fingers up underneath to caress them directly so my eyes and hands could feast on her. I let my fingers slip down between her labia, at first rubbing up and across her clit with my fingers until I turned my hand over to press it against her body and let my thumb caress her clit. As continually aroused as I’d been since I got there, without having cum yet, her bouncing up and down on my cock was all it took for me and my body began filling the condom in her pussy. In this position I could keep the pressure on my pelvis, keeping my erection going, and soon I recognized the quivers beginning in her body. When her two hands came up to play with her own nipples, pushing mine away, I increased the pressure around her clit with my thumb until she began shaking and shuddering. Unlike when I was in her ass, her hand came down and pushed against me, telling me to stop. Apparently sated, for the moment, she climbed off and lay down next to me. I had my arm out; she cuddled against my chest, and relaxed — I thought she was going to fall asleep.
“That was really nice,” she whispered.
“Glad I could be of service”, I laughed quietly. She didn’t say anything for a few moments; we just lay there. I felt her body relaxing, her heart slowing, until she inhaled and let out a long, satisfied breath.
“Why did you hate Robin?”
“What?” I said, taken aback at the question of which the opposite was the truth. “Me? Hate Robin?”
“That’s what she always thought. She said you always just headed the other way and ignored her whenever we were around.”
“Oh my God, no. If anything, it was the other way around. I thought I had no chance with a girl like Robin. I always thought she was too far out of my league. The head cheerleader, the girl with the star quarterback boyfriend…”
“You’d have been a lot better for her than that… dick… she dated.” She giggled, “My God, I think he almost ruined her,” she said, reaching over and once again gripping my now flaccid cock. “He may have been bigger, but I don’t think he had anything on knowing how to use it like you do.”
I remembered overhearing Martha on the phone telling my mother about seeing Robin and Adam, who I assumed was the dick she was referring to, but I didn’t think she knew that I knew. “Adam?” I questioned innocently.
“Oh my God, did you know him? I came home early one day and found them fucking on the living room floor. That kid had the biggest dick.”
“And you saw it?” Her nod confirmed what I was asking.
“He was a dick too. They weren’t actually fucking when I got there, she was giving him a blow job at first, but then when he got close, he had her climb on and ride him cowgirl.” She shook her head. “He was, to say the least, well endowed. But he thought he was God’s gift to women, so he treated her like dirt. Best thing she ever did was to break up with him.” It was me who nodded in understanding this time.
“Robin…” I said, bringing the conversation back to where it had started. “I didn’t hate her. Just the opposite. She was always my fantasy girl growing up, just… unattainable for me. I always felt like she wanted nothing to do with me. When she was around, I always felt that I was just a ‘nerd,’ just some dweeby son of her mom’s friend. I always thought she didn’t like me. When I danced with her at her wedding, she wouldn’t even let me hold her. Not close at least.
“You never knew she had a bit of a thing for you? I suspect, even then, she was thinking that maybe you were a better match than the guy she had just married. You were a bit younger, but that makes less and less difference as we get older. But she always told me she thought you didn’t like her.”
I laughed. “I guess I can tell you now, but I used to masturbate to thoughts of your daughter.”
“No, she didn’t dislike you,” Martha said moving back to my previous sentence; “she always had a bit of a crush on you.” She giggled. “I know she’d be upset if she knew I got you and she didn’t.” We lay there quietly for a moment, me thinking about the revelation that Robin really hadn’t hated me. I wondered what might have been if I hadn’t been such a dweeb, if I’d had the self-confidence to take the first step, even to just say hello.
Martha shifted on the bed, her hand reaching behind herself. “Oh my. That was all well worth it, but I think I might walk a bit funny tomorrow.”
“Hurt?”
“No, not really. But I can still feel you up there.” She rolled over and looked at the clock. “Oh wow, that went quick. It’s time for me to go. My husband will be wondering where I am.” She rolled onto her side, toward me. “You were really good.”
“Thanks.”
I waited for 5 minutes after Martha walked out before I left, just in case we saw someone we knew, but all the time thinking about what had transpired. I couldn’t help but wonder what my mother would think if she knew I’d just fucked one of her best friends, especially that I’d fucked her in the ass. A shudder went through me, as the off kilter thought of wondering if my mom and dad did anal sex, admitting that if they did — I really didn’t want to know. My mind shifted to Robin, evaluating that Martha had said she’d always had a bit of a thing for me, just as I had for her.