by Connor

Gender: Male
Age: 61
Race/ethnicity: White
Current location: Wisconsin
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Attorney
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? That’s hard to answer, especially if you are asking about ladies that explored me as I explored them without having intercourse, which was common in the 60s and 70s when I was a young man, primarily because oral contraceptives were new and even condoms were something that had to be obtained from a gas station men’s room because pharmacists would only sell them to married people. If you include all the groping episodes in high school, college, and law school, I would have to guess something near 100, and I’m not exaggerating here to myself sound like I was a stud or something, but that’s pretty much how it was.

How many hookup stories have you here posted before? None

Unexpected Client Introduction

How long ago did this hookup happen? Six months ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was a jaw dropping 19 year old who was attending a local community college. She was about five and a half feet with big round eyes that made her look like the most innocent little girl you could imagine. She was thin and had curves that were amazing for someone as young as she was. Her breasts were fairly large for her petite frame and, being as young as she was, had not an ounce of sag to them. Her legs to her slender waist were just amazingly proportioned.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had a client with a difficult insurance claim against her home owner’s policy arising from a fire. The insurance company disputed her lost personal property claim regarding several high value items that they didn’t think anyone in such a modest house could have. The client had no receipts, as most of the items were gifts from aging relatives who were doing some pre-death distribution of assets, and no photos containing the objects in the background, either. I had to start looking for witnesses who could testify to having seen these items, and describe them in a way that would convince a court that they really existed. That’s how Lucy’s name was given to me. She turned out to be a lot more than a mere witness. I played basketball in my younger days because I was somewhat tall (6′ 5″) and built sort of lanky. I’ve filled out a little as I’ve aged but most would still describe me as tall and thin, plus being muscular even at my age because of three decades of going to a health club several times per week to swim in order to keep my heart in shape followed by some moderate weight room work to keep myself trim with a little muscle definition. During the interview, Lucy was showing a lot more interest in me than a young woman that was forty some years younger than me should have. I have all my hair, it’s turned grey, and a lot of people tell me after meeting me that they would have guessed that I was a lawyer because I looked “distinguished.” Lucy probably had some daddy issues because she, too, started telling me that she thought mature, distinguished looking older men were far more sexy than the guys her age who had little more interest than seeing if they could get into her pants. I hadn’t received attention like that from a young, beautiful, woman in a long time and, even though I know that I should be keeping things on a professional level, I couldn’t help myself. She had the kind of beauty that would make most men just want to protect and care for her, and I found her charms irresistible. At first I thought that she was probably just being a little tease so that she could tell her friends about what an old fool I was but, as the interview went on, I started thinking that she might really mean the things she was saying about how immature and unable to please guys her age were, and that she preferred the slow touch and sensuality of an older man making love to her rather than merely having sex with her. I finally decided that I would either prove that she was, indeed, urging me onward to making a total fool of myself, or that she really meant what she was saying. I suggested getting a hotel room, and was shocked when she agreed. She went with me in my car to a higher end suite hotel and waited as I rented a room. I picked her up at a side door so that no one would see us and we went in for what turned out to be about seven hours of amazing pleasure. At least, it was for me. She, too, said that it had been amazing, but you never really know what a woman is really thinking, which may have been betrayed by her insistence as I drove her home that this had to be a one time meeting. I was actually glad that she said that because I have a wife of five years who really does rock my world, and I would never want to do anything to put me through a third divorce, which I know would happen if she were ever to find out about this afternoon and early evening tryst.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Lucy had told me that she liked mature men because they took things slow and sensual, so I took my cue from that. I ordered a bottle of wine from the hotel’s bar and, once it came to the room, we started out by talking for quite awhile as we probed each other’s life. I wasn’t her first mature man, although she did tell me that I was the oldest. She kept complimenting me on how little I looked like my age, and that I was more physically appealing to her than a couple guys that she had been with who were ten or more years younger than me. When the wine was nearly gone, I suggested a shower as a means of introducing ourselves to each other’s body. We were in there a long time, soaping each other up and exploring each other’s body. She brought back long lost memories of just soft, yet firmly stretched, the skin of such a young woman is. We dried each other off and went to the bed where we continued to engage in mutual exploration. I had been concerned about getting an erection because I was at the age where I sometimes failed to perform for my wife, and the fears that arose about repeating with a young woman didn’t help. That was wasted energy, as it turned out. She looked and acted so sexy in the shower that I achieved an erection reminiscent of my twenties. By the time we got to the bed, I knew that I had nothing to be concerned about in that regard. I played with her breasts with one hand and my mouth, while my other hand caressed her buttocks and held them tightly against me. She was very vocal about what felt good, and she told me how much that stimulation turned her on. I have no idea how long we gyrated against each other like that, kissing passionately whenever our mouths drew close enough, but it was a slow episode like she had told me she liked. I eventually moved down toward her vagina and began to tease her clit with my tongue while using the palms of my hands to brush her erect nipples ever so softly. That was something that my wife liked me to do during foreplay, so I decided to see if it would work for Lucy, too. Her reaction was incredible. She moaned and writhed in what appeared for all the world to be intense pleasure, arching her back so that my mouth and tongue fell on her clitoris at just the angle she wanted. She also encouraged me to keep lightly brushing her nipples, telling me that she had never felt anything like that before because all that the young guys wanted to do was squeeze her breasts, which wasn’t stimulating to her and usually was somewhat uncomfortable. She closed her legs so tightly around my head that I couldn’t move it when she thrust her vagina into my face. She said that she had an intense orgasm, which I suspect may have been true because I could feel her thigh muscles tighten and begin to quiver. She asked me to stop when it was over because she said she was too sensitive to have me touch her. I got the wine glasses while she caught her breath and we finished the bottle of wine as we leaned against the headboard of the bed. She was using her left hand to massage my penis, which was so erect, and the head so purple, that it felt like it might explode. She kept me aroused while she regained normal breathing, after which we went back to it. This time it was her being intent on pleasing me orally, but I warned her that I didn’t want to orgasm that way because I really wanted to be inside of her. She brought me continually to the edge, but backed off when I gave her a warning. I asked about a condom, which she said that we should probably use because she wasn’t on the pill. I let her know that, if that we her only concern, I had had a vasectomy twenty years before so pregnancy wouldn’t be a potential problem. That ended that discussion, and we set about to enjoy vaginal sex with her on top to start, and again stopping her grinding motion when I told her that I was getting close, and ending in a more traditional missionary position where I had probably the most intensive orgasm of the last couple of decades. We ordered another bottle of wine, which I took at the door wearing one of the hotel’s robes, while she hid in the bathroom. We spent several more hours of just talking about anything and everything as we finished that one, too. I assumed that I was through for the day because it had been many, many years since I had been able to obtain two erections during one love making session. She started manually massaging me, though, and, as I began to respond, she followed it with more oral sex until we were able to return to vaginal sex once again. This session lasted a long time because I had very little sensation and assumed that obtaining the erection was the culmination of my abilities. We tried several positions before, to my utter amazement, I felt an orgasm coming on while I was standing behind her as she knelt on the edge of the bed. The sight of her head and shoulders down on the bed, as her hands clawed the sheets, and her amazingly shaped ass upright as I was sliding in and out of her was just too sexy and I had another intense orgasm, although it wasn’t as intense as the first. I was totally spent as we finally dressed and I drove her home, calling my wife to say that I had been delayed at the office and would be there soon. All that night, as we cleaned up after dinner and spent time talking about the day, I was living in fear that my wife would suggest that we go to bed early so that we could have some playtime before we fell asleep. She does that a fair amount, which is usually welcome, but I knew that it would totally embarrass me if she asked that night. Fortunately, it didn’t, and I now have an amazing memory of a long, sensuous, bout with an amazingly beautiful young lady at my ever advancing age. I guess that I’m ready for the angels, now, as life can’t possibly get any better from here on out.

Did you have an orgasm? Did your partner(s)? As noted above, I unexpectedly achieved two, for the first time in a very, very, long time. Lucy said that she had “many,” telling me that, if she’s with a man that doesn’t just want to get in, get out, and get on (her way of describing young men), she can be extremely multi-orgasmic with what she calls a series of rolling orgasms. I have only her word that it happened that day, but I suspect that the time she squeezed my head so tightly between her legs was something that she probably didn’t fake.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We took no precautions. She said that she trusted that I hadn’t been doing anything that would have gotten me infected because of the fact that I have a wife at home. She assured me that she didn’t take chances at all and was only concerned about pregnancy. When she found out that I had a vasectomy, and being assured that I wasn’t someone who was having multiple trysts with a different partner every chance that I had, she told me that she would prefer that we not use a condom.

What were your REASONS for having this hookup? I was just flat out stunned by her beauty, even more than I was amazed that she would show an interest in someone my age.

Were alcohol or drugs involved? If so, how much? Not when we got the room, although we had two bottles of wine once we started.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We parted with smiles. Lucy let me know that she wasn’t looking to ruin a marriage, and didn’t want a sugar daddy, not that I had offered, so we should accept it for what it was and let it go at that. I felt much the same way because I didn’t want to do anything foolish that might jeopardize my very happy marriage.

To whom did you talk about the hookup? How did they react? Absolutely no one!

Was this a consensual and/or wanted experience for you? For your partner? Very much so.

Do you regret this hookup? If so, why? Not in the least.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was that, for several hours, I was back in my youth and enjoying the pleasures of an amazingly beautiful young lady. There were no bad parts about this occurrence, so obviously there wasn’t any “worst” aspect to it, either. It hasn’t changed my outlook because I’m experienced enough in life to know that this was one of those once-in-a-lifetime events that will never be repeated.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative
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