My paid sexual encounter with a 69-year old woman

I will start from the beginning.

I have always been attracted to the idea of paid sex with a stranger that I just met for the first time, but have never lived out the experience. The appeal is tied the thought of having an encounter where there are truly no strings attached and the whole reason for being in the same room is to simply have sex. There is also an "I'm in charge of this." edge to the fantasy that is not something that ever happens in a normal sexual exchange.

I recently had a small financial windfall and decided that it was time to live this fantasy for real. Just the act of making the decision to do it was enthralling. The next step was to "shop" for the woman I would hire, and the task was akin to being a kid in a toy store with a wad of money. I know that doesn't really paint me in a positive light, but it's what it is. Just the act of looking was a fun and extremely satisfying activity.

I went onto Backpage and watched it for several days. Most of the posts there are of the same women over and over. There were some "young Asian" posts that were clearly human trafficking and were upsetting to see. Many of the posts were of women who were working out of their homes, and some appeared to travel from town to town with windows of availability.

It is a difficult thing to hire a prostitute without exploiting someone. I hate the thought that there are woman in abusive relationships with men who are forcing them to sleep with Johns and hand over all of the money. I would be horrified to think that I am supporting that, but at the same time I've always been a firm believer that all woman and men have every right to sell her body should they choose. My difficulty was to find someone who was really doing this of her own free will and was not being forced.

In the end, Backpage didn't have what I was looking for. I came close a few times to making a phone call just to move things along, but I needed to find the perfect partner for this fantasy. In doing Google-checks on some of the woman, I discovered a review site with paid membership, but considering what I was willing to pay, this didn't seem like a bad investment to be able to read actual reviews.

I've always had a thing for older women. I am 42, so for me older is bordering on downright old. The review site had a few search features, one of which was the ability to search by age and number of positive reviews. It was by using this search that I found Cheryl. Apparently, she was active in the early 2000's, but retired in 2007 and then had very recently returned to the profession.

She had her own web site which had some photography that her late husband took of her. The site had a link to an archive of her old blog that she ran for some time. It was obvious from the blog that she and her former husband were into the lifestyle and enjoyed a very open sexual life. She was now 69 years old – a few years older than my mother.

She was a extremely attractive. I would describe her physical appearance as handsome. She was gray/blond and had wonderfully large natural breasts and chiseled facial features. Her breasts had succumbed to the pull of seven decades of gravity, but this only made them all the more attractive in my opinion. Her body had what I would consider to be the perfect amount of padding. Full, curvy, but still fairly tone at the same time.

With my breath short and heart pounding, I picked up the phone and called her. Fortunately for my nerves, she didn't answer and I got her voice mail, but I managed to leave a quick upbeat message that didn't sound too creepy. I left my number and she called me back in a few hours.

When I answered the phone I was surprised by how young she sounded. She was very chatty and personable and I quickly overcame my nervousness. We wound up chatting for around 15 minutes and I learned that she lived by herself on a farm a few states south of mine, but grew up in my city and returned several times a year. She wasn't due to return for another few weeks, so I booked a date to go meet her and she said she was looking forward to meeting me in person. I asked to have two hours with her and she said that would be fine with her.

I won't go into too much detail about how those two weeks of waiting were, but I'll say that the anticipation of what was to come was both incredibly sweet and maddening at the same time.

When the morning of the day finally came, I called her and she let me know she was at a hotel near the airport. She gave me her room number and I was on my way. Traffic was lighter than I expected it to be and I showed up 20 minutes early, which wasn't an issue for her. She told me to come over as soon as I got in.

I knocked on the door and she answered it inviting me inside. She was absolutely like her pictures, and looked incredible. She wore a lightweight black sundress with nice jewelry and a push-up bra. She had some soft jazz going in the background and smiled warmly. She surprised me by stepping right up to me, giving me a hug, and kissing me gently on the lips.

The kiss was warm and sensual and after my initial shock, I kissed her back. She tipped her head slightly to the side and the kiss morphed from a greeting into something more passionate, but still soft and sensual. She was as tall as me and fit into my arms perfectly. I held her waist with one hand while the other held her upper body in a light hug.

She broke off the kiss and invited me inside. The room was an extended-stay suite and had a small kitchen and a sitting area with a sofa. She sat down and patted the cushion beside her. I felt like an idiot telling her that this was the first time I had done something like this, but she shrugged off my statement. I'm pretty sure she could tell I was a little nervous, so she began to chat with me again.

I wouldn't say that we had a lot in common, but the conversation flowed easily anyway. Our talk turned from her life at her farm in the country to my work and eventually to sexual matters. We discussed likes and dislikes and past experiences for about 15 minutes flirting the hole time.

It was my turn to make a move. I took her hand in mine, leaned over to her, and kissed her again. My kisses were soft and teasing and she followed my lead. I'm not sure why, but it's important to my story that you consider that she had the normal skin of a woman her age. She had the sun spots, crows feet, wrinkles and other qualities that are the hallmark of life.

I don't know why it is, but this detail is perhaps one of the most erotic parts of the whole encounter to me. My kisses left her lips and traced along her cheek and to her neck. She had long gray-blond hair and I brushed it aside to kiss my way to her lower neck and bare shoulder. Her breathing responded as my journey progressed and she appeared to be as truly into the moment as I was.

I pulled her to shift her position so she was straddling me on the couch. This left her in a dominant position to kiss me, but also freed my hands. As she leaned down and our lips met again, her tongue entered my mouth which was unexpected. We made out like teenagers swirling our tongues playfully together while my hands found their way over her dress touching her body everywhere.

Eventually, they found their own way up her thigh and under her skirt only to find she was wearing no underwear. She had a larger ass, but larger in a very good way. Her cheeks were youthful and firm, and they rocked gently as she lightly ground herself on my hardness pressing through my khakis.

My hands left her wonderful ass to continue their journey under her dress where they next encountered her bra clasp. With only minimal fumbling, I was able to undo her bra and she sat up to help me remove her dress and bra in one motion.

The picture at this point is me, sitting on the couch fully dressed with her fully naked body straddling me and slowly rocking back and forth while we kissed. If I had been watching this while fapping on xtube, then this is the point where I would have released, and after several watches, I probably still would have had a hard time making it past it.

In fact, I had a hard time not cumming right there in my pants. I'm not necessarily the best sexthlete and don't have a long window for stimulating before I cum. To cope with this, I suggested we move from the couch to the bed. She agreed this would be a good idea and we both stood up together.

At the edge of the bed, she moved behind me caressing my body with hers. Her hands slipped around my front to caress my covered erect penis to and under my shirt to stroke hairy chest before unbuckling my belt and pushing my pants to the floor. In short order, I was equally naked and she climbed into the bed pulling me with her.

We tangled our bodies together and made out some more just enjoying the feel of it. I spent some time playing with her wonderfully heavy breasts sucking on her hard nipples while my fingers found her womanhood.

She was wet. Really wet. My fingers slid over her labia and clit teasing her opening with no friction whatsoever. She waxed and was totally bare which is normally a turn-off for me, but in this case it fit with the moment. I moved into more of a sitting position to view her body, and this adjustment put her head in close proximity to my penis.

Before you respond with comments chastising me for what happened next, let me just say that I know this was dangerous and I should have put on a cover immediately at this point. Had I been in my right mind, that's absolutely what I would have done, but when her lips and tongue began to trace their way over my shaft I was frozen with a sexual flood.

She slid my bare penis fully into her mouth and I've never felt anything so incredible. Her suckling was soft and warm, and she moved slowly sensing that my sensitivity was very high.

I adjusted my position to get closer to her kitty and found her large labia and vulva slightly spread with a very wet opening. I rested my head on her thigh for a moment and breathed her scent. She smelled incredibly sexy – musky, but clean.

She took me all the way in her mouth and I moved the rest of the way in to kiss her clit. My delicate clitoral kisses turned into licks which then turned into full blown cunnilingus.

Between her juices and my saliva, she was soaked as was my face. Without breaking contact, she rolled me from my side onto my back and moved her lips from the head of my enormous cock all the way to the base and back again with a smooth steady cadence.

I don't claim to be any kind of a stud, but I do have a well-above average cock. It's just shy of 8" and is quite girthy with a full blunt head. Because of this, I had never experienced what she was able with her mouth and throat to do that no woman before her could.

Now that I was positioned under her, her vagina was fully spread before me and my tongue traced its was in and out of her opening. Every once in a while, I would hit the right spots and she would stop attending to me long enough to softly moan and breath heavily while continuing to stroke my sloppy penis with her hand.

It was doing one of these moments that my buildup hit the breaking point. I tried to tell her that I was about to cum, but she already knew and her mouth returned to fully ingest my entire orgasm. I had not fapped for the full week before meeting her that day, and my release was nothing short of epic. She swallowed every drop.

At 42, the recovery time is not so quick anymore. This was why I scheduled 2 hours. By now we were only a half-hour in, so we cuddled together and let the glow happen for a bit. Eventually we fell into another round of small talk which descended into us watching funny youtube videos on my phone. She had a wonderful laugh.

I would like to report that round two was every bit as hot as round one, but if I'm being honest I had some performance issues at the start. The act of putting on the condom did not help this at all, but she was very understanding and was able to help.

I did eventually rise to the occasion and we had sec in a couple of different positions, cowgirl and missionary. I would stop short of saying that we made love, but it was slow, sensual, and passionate.

I don't think that she had an orgasm during the actual sex, but she did appear to lose herself to the experience all the same. Her breathing and light moaning permeated my ears while I ground deeply inside her. She had gotten very wet again and it was audible. We took turns kissing during, and I spent time kissing her neck. Eventually, my second orgasm overtook me and I held her tightly to me as I entered her all the way and filled my condom.

After that, there's not a lot to report. We cleaned up and said our friendly goodbye's. I had forgotten to place the envelope with her payment on the end-table when I arrived and to her credit, she never brought it up. I found it in my pocket as I was getting dressed and blushed and handed it to her.

I gave her one more squeeze and a kiss on the cheek and was on my way.

The fantasy was everything I hoped it would be, but I don't know if I will ever need to live it again. I always say the fastest way in the world to kill a sexual fantasy is to live it out. I would be lying if I said I wasn't overcome with some conflicted feelings over the whole thing. I do feel that, even though she was of completely free will, I sill exploited someone. I also feel ashamed of what society would preach is a deviant act and that I do not have the willpower to avoid situations like this.

On the other hand, well, I'll always have the memories and visuals. She really was truly incredible.

Source: reddit.com/r/gonewildstories/comments/3a6jl8/my_paid_sexual_encounter_with_a_69year_old_woman