I. I was 15 and lost my virginity to a 13 y.o. in the women’s bathroom at a gas station where I worked. This was late at night, just before closing. I did lock the door. Actually, that’s not totally accurate. I tried to lose my virginity, but being a dumb kid, I couldn’t find the opening and ended up ejaculating all over the poor kid’s pubes. Made up for it the following night where we did it in my car and she helped me get it inserted.
2. A week later I was out cruising the streets in the city when one of the guys riding with me asked a really good-looking girl standing at a bus stop if she was selling it. She fucked all three of us. We flipped a coin and I got to go first.
3. Then a few days later another schoolmate and I picked up two teens hitchhiking from NY to FL. We went to a local park and I fucked one of them, but he didn’t fuck the other one. We had separated in the park and when I told him later that I had fucked the one I was with, he was really pissed on missing out. The girl I was with admitted they were fucking their way to Florida.
4. In my senior year of high school I started going with a 16 y.o. I was 17. We fucked four or five times every week for a year until I graduated. Then we got married shortly after she graduated.
5. While going steady with #4, we split up for a short time and I dated another schoolmate who was 15. We went to a party together and fucked in the front seat of my car parked in the driveway.
6. I went away to college and took a high schooler on a picnic and fucked her on the backseat of a ’51 Pontiac that I had borrowed from a buddy. She was very wet, and I accidentally slipped it in her ass but corrected it quickly once she pointed out my error. That was my first anal experience. I was 18.
6a. Any sex in my college years was hard to come by because I lived in a rooming house with a roommate, all the girls I dated lived at home, and I had no car. So, there was no actual place to do the deed. I managed to borrow a friend’s car a few times but only scored in it once, described in #6 above. I did date a high schooler who lived within walking distance of my rooming house. I used to go to her house in the evenings and sit in the living room with her parents and watch tv. They always went to bed very early, like 9 pm. After they were gone, we would get busy. She jacked me off a couple of times, cumming into some paper towels. But it was very risky, so most of the time it was just kissing and me feeling her up and her squeezing my dick through my pants. She insisted I take the cum-filled paper towels with me when I left because she was afraid her parents might smell it. Probably a legitimate concern.
6b. Another high schooler invited me to a home cooked dinner when her mom, dad, and older brother took off hunting for a week and left her alone. After a nice dinner we got busy and eventually got totally naked in her bed and fucked. She had a super nice body but frankly she really wasn’t a great sex partner. Also, too much “will she or won’t she” when it was very obvious that she wanted to fuck as much as I did. That was the only opportunity we ever had to do anything.
6c. My roommate and I used to hang out at a local pizza parlor. The evening shift was handled by the owner’s 20-something daughter. Both of us had a terrible crush on her. The place stayed open until 10 pm and we were usually there until closing time. She enjoyed our company because business was slow at that time of night. Even though she was a lot older than we were, we seemed to be able to carry on interesting conversations. One night I was there by myself and the two of us were sitting across from one another in a booth. She slipped off her sandal and planted a bare foot right on my crotch. She started rubbing her toes on my cock. This shocked the living shit out of me. Instant hard-on. If she hadn’t been interrupted by a customer coming in, I think I would have cum in my pants. Once the customer left, it was like it never happened. Nothing like it ever happened again and it was never even mentioned. And I never told my roommate.
7. Coming home on a train from school for a visit, I was seated next to an attractive high schooler. After everybody went to sleep, we screwed each other. It was incredibly hot. And very risky.
8. Met a co-worker while I was married and got into a super hot and heavy relationship. We had sex whenever possible. My marriage was already in the tank, but this helped seal the deal. Our affair ended her marriage as well as mine. We finally stopped seeing each other because the stress was causing her hair to fall out.
9. In the waning stages of marriage, we had a house party. Everybody got shit faced. I hooked up with some hottie and ended up taking her into the woods in back of the house and fucking her. I don’t even know who she was. There were so many people in the house that nobody missed us.
10. About this same time we went to a Halloween Party and I was sitting next to an attractive gal in a cat costume. The way she was sitting, her pantyhose had pulled her tights away from her body and I could actually look down and see her pussy lips protruding through her pubic hair. I told her I could see her pussy and she asked me how I liked it. It was a split-level house and I managed to get her up to the entry level. She wouldn’t go upstairs to a bedroom, so I pulled her into the coat closet and fucked her. It was very difficult and very cramped but also very hot. My wife had been helping the host in the kitchen and amazingly nobody even missed us. I still don’t know who the girl was.
11. Final straw with my marriage was my wife refused to have sex one night. Told me to go get it somewhere else. So I went to her recently divorced best friend’s apartment and she fucked my brains out. We did it on the living room carpet to avoid waking her baby in the only bedroom. I came home with knees and elbows raw with carpet burn. Wife asked how it happened. I said, “How do you think?” That was the last time we were together as she kicked me out that morning.
12. While still married, I literally got seduced by a co-worker and I used to meet her after work at her house. Her husband was a fireman and worked really odd hours and would be gone for several days at a time. We also screwed in my car during lunch time. One time she got my cock out in the office in a remote hidden area and jacked me for a bit but not all the way. No place to shoot my cum but super erotic anyway. We called it quits because she was committed to staying married and she said that our relationship was spoiling her for her husband. Sex with him was boring compared to what we were doing. Hopefully she got it re-ignited with hubby.
13. I was working at a new job and the place had a smoking hot receptionist. I tried chatting her up, but she cut my legs right out from under me. I had a remote garage where I worked on a race car I owned. It was across the street from a well-known landmark. I guess the receptionist overheard me discussing the garage and its location with some co-workers. I also mentioned that I was there almost every night. Damned if she didn’t turn up there one night in super short shorts and a halter top showing off a great body. It didn’t take me long to figure out she wanted to get fucked. We got together a number of times, but she was getting a bit too needy, and with me being married, I didn’t want any complications. She was engaged to be married and didn’t want anything to do with me at the office and, according to her, she was holding out on her fiancée until he married her. But still needed some sex which was where I came in.
14. Also while still married, I was involved as a part owner in a business event that was about 90 miles from where I lived. I used to drive there on a Saturday, work the event, and come home very late. One time one of the girls who worked there asked me if I could drop her off at home after everything shut down. As soon as we left the site, she was all over me. I pulled into a little used road and we fucked. I did it with her one other time. She was also married.
15. And at this same event, another girl and I spent the night together at a local motel because I was too tired to drive all the way home but not too tired for a piece of sweet ass. She didn’t spend the night because she lived with her parents and had to go home. This girl and I also flew to another city for some industry events. She was only 18 and I was 32 or so. Somehow her parents got wind of what was going on and that was the last I ever saw of her.
16. At another event that I was working as a photographer I met a gal who I invited into the back of the van I was driving, and we proceeded to make the beast with two backs. One and done.
17. I had a part time evening job working on a local newsletter. The place was next door to a beauty school and when the students were coming and going, me and the guy I worked with used to stand out front and flirt with the girls. One evening we got one of them to come into the shop and we took turns fucking her in a back room on a broken-down old sofa.
18. I used to work on my car at a friend’s shop and as a gag, he told a woman friend of his that I was only 17 years old, and a virgin and she needed to take my cherry. She was probably about 35. We climbed in the backseat of one of the cars in the shop and she got my cherry. But the truth is I was married with three kids and 26 years old, but I could pass for 17. I never knew if she found out the truth.
19. I attended an event with a business partner. This was a huge deal and every hotel and motel was packed. Hookers were out in force. I really wasn’t interested but my partner would fuck anything that breathed and somehow he corralled two girls and got them back to the room we were sharing. I honestly wasn’t into it but I kind of went along to get along. I also wasn’t keen about fucking somebody in the same room with him, but I had paid my girl and was putting it to her while he was still arguing with his over the price. He was one of those guys who prided himself on getting the best deal. Which was stupid to be wasting her time while guys were lined up outside waiting to hand her whatever she asked. I finished up and the two girls left leaving my partner high and dry.
20. I flew to a west coast city to meet some guys at a local hotel about a business deal. Halfway through the meeting they gave me a room key and said they had a surprise for me. A very attractive lady was waiting for me and I proceeded to take advantage of why she was there.
21. Between marriages I met an extremely cute girl at a local nightclub. We got into a relationship but again, due to age differences, it really wasn’t going anywhere. I think she was only 19. But we did have a lot of really quality sex together. We even flew to a couple of resorts together.
22. I was part of a committee that worked on staging a trade show. One of the gals on the committee and I really hit it off. We carried on a terrific coast to coast relationship for quite a while before she met some guy and got married.
23. At the time I had a west coast office and the guy who ran it for me introduced me to a very hot waitress who worked in Marina del Rey. I hooked up with her a couple of times on west coast visits. The odd thing was, she was in a relationship with a cop, but when she knew I was coming to town, she flat told him she was unavailable. Maybe they had an open relationship because she told me not to worry about him. I figured anybody who carried a gun had to be worried about.
24. Same thing again with my west coast guy hooking me up although this girl was an airline stewardess. Due to my travel schedule and hers, we only got together once, but it was memorable. Her thing was she wanted to be in positions where she could clearly see my cock going in and out of her pussy.
25. Again my west coast guy introduced me to a former Penthouse Pet centerfold. Smoking hot chick but again due to scheduling issues it was a one-time thing. She did give me a wooden plaque with her centerfold encapsulated with a very sexy autograph written on it. Something like “You were great last night. Hope we can do it again.” I still have it someplace.
26. Another stewardess. This one I met on a coast-to-coast flight in first class. The front cabin was basically empty, so she sat with me almost the entire flight. Unfortunately, she couldn’t hook up with me upon our arrival, but she took my phone number and said she would call the next time she was in my city. I figured I would never hear from her, but she did call. I didn’t get to fuck her, but she did give me a blowjob in the parking lot of a nightclub. We were supposed to hook up again, but she accidentally gashed her thigh on some glass and by the next time she had a flight to my city, I was in a relationship.
27. I had two friends visit me from the West coast and I took them to the famous 2 O’Clock Club in Baltimore. An extremely cute stripper sat with me and without me even buying her a drink, she jacked me off under the table. Then gave me a kiss and said she had to go back to work.
28. I was working an out-of-town event where the promoter invited me back to the motel. He had me go through a connecting door to another room where two super high class Atlantic City hookers were waiting for me. They took turns blowing me, one with ice water in her mouth and the other with hot water. It was total heaven. I then got a shot at fucking each one. I found one of them super-hot, so I finished off deep in her pussy.
29. I was visiting a west coast city and went to a strip club by myself. One of the girls was super attractive and I had an overwhelming desire to fuck her. So I made her an offer and much to my surprise she showed up later at my hotel. I fucked her both vaginally and anally.
30. I had a temp working for me over school vacation. She was 18 and just out of high school. She had really great looking legs. I had tried to fuck her a couple of times, but she resisted. She claimed she was a virgin and saving it for her husband. She gave me some of the worst blue balls ever. Finally on her last week working for me, she told me she was ready to give it up. No way was this girl a virgin. The most memorable thing she did was rub the head of my hard cock all over her face before sucking it.
31. I got connected with a very famous beautiful woman. She was only 22 and I was 32. I can’t go into any detail at all, but we had an extremely hot relationship. Even though she was a lot younger than me, she taught me a lot. Especially on the fine art of eating pussy. After we split, she became even more famous. Our whole time together was on the downlow. Nobody ever knew what we were doing. We parted company because she was only a sometime partner and I connected with a regular partner who ultimately became my second wife.
32. I had a friend who owned a night club. I wasn’t really a night club person but one evening I stopped in just to say hi. He introduced me to an extremely cute girl and before the night was over, we were in my apartment fucking the night away. It was a one-time thing because we were both in relationships with others. One thing she did that I will always remember. I was flat on my back and she was sitting upright on me with my cock buried in her pussy. She was kind of squatting over me and grabbed both knees and pulled her legs as far apart as possible. She bounced up and down on my cock and asked me if that didn’t feel just like I was getting a blowjob. It actually did, and I came in no time flat.
33. Sometime before my second marriage I was cruising some night clubs and met a real cutie. Another young one. I think she was 19 and I would have been 32 or 33. She was a terrific sex partner. We dated off and on, but I was also seeing another woman. I flew her with me to Florida one time for three days. While there she informed me that she was pregnant and as soon we got back, she was marrying the baby’s daddy. So that was the end of that one.
34. I met a girl who lived in my building. She was super attractive, and we had an incredibly erotic relationship. So much so that I married her. We were together for 25years.
35. While living with my next wife but before we were married, there were two stews who lived across the hall from me. My gf was out of town and I struck up a conversation with one of the stews in the laundry room. Her roommate was gone for several days on a flight and she was lonely. She actually asked me if she could come watch tv with me. We did and really nothing happened until she asked if she could spend the night. Has a cat got an ass? Of course, the answer was “yes.” Another one-time thing but we did have some really great sex. Again, with her living across the hall I didn’t want to get something started.
36. This was a strange one. I used to get together at a local restaurant with a group of football fans. Some of the couples I knew quite well but there were two or three who were friends of friends who I really didn’t know. One of the women was quite attractive and she was always very outgoing and friendly to me even though I really didn’t know her. One time when my wife was out of the country visiting her parents, this gal shows up at my door. She knew my wife was gone because it had been discussed at our meeting. I really didn’t know this woman, but she obviously wanted to get fucked. So I took care of it. Another one-time thing.
37. I was at a trade show in Europe and a group of us guys were celebrating one of the guy’s birthday. After dinner our host drove us to a very upper-class brothel. We sat around in a nightclub atmosphere having drinks, but only dressed with a towel around our waist. The girls, all dressed in heels and thong bikini bottoms (topless), would roam around and stroke our cocks under the towels trying to entice us to go upstairs and fuck. The trick was to sit there because in a period of an hour or two, you would get your prick stroked by 20 different women. Our host warned us not to give in too quick. But after a half hour, I couldn’t take it anymore. I went upstairs and got laid.
38. Same night. After my first session and a few more drinks and getting my hard-on stroked some more, I had to go again. Lasted longer the second time which was a bit frustrating for the girl.
39. Two years later I’m at the same trade show and go to the same brothel again. But by myself. The rules had changed. The girls were not permitted to stroke the patron’s cocks, although they did it anyway, but not as much and more secretly. After about the fourth girl gave up trying to entice me upstairs, one of the most beautiful girls I can ever remember seeing sat down with me. She literally had a perfect body. She was only about 5’ 3” but drop dead beautiful. I really wondered why somebody with her looks was working in a brothel. But upstairs we went. I normally would not go down on a hooker, but I couldn’t resist. I even tongued her sweet asshole. She was a very lively and a fabulous sex partner.
40. I was invited to a big off-road party in the desert in Southern California. Late in the day we were all standing around a big fire drinking tequila. An attractive girl came up to me and offered a lime and a bottle of tequila and said I could lick the salt off of her hand. She asked where I was staying, and I pointed to a rather large motorhome that I had rented. She wanted to see the inside, so we went in and immediately were trading spit around. I made an attempt to take it further, but she was concerned about being gone too long and that the guy she was with would be upset. She gave me her phone number. Unfortunately, she lived a good two-hour drive from where I lived. But by chance I had an event that I had to be at in a couple of weeks that was in her city. I called her and made the date. She was going to meet me at my motel, and we would go to dinner. It was cold on the desert and she had some bulky clothes on, so I had no idea what her body was like. She arrived at my room looking like a school teacher. She was wearing a suit with a skirt, but it was also kind of bulky and she also had sensible shoes on. I was disappointed because I was expecting something kind of sexy. I sort of wrote the evening off at that point. But she had different ideas, because when we got back to my room, she immediately undressed to display a rocking body. Great tits, narrow waist, flaring hips and was a fantastic fuck. I was shocked by the treasures she had been hiding in her shapeless clothes. Due to the driving distance and that I was married, it was another one and done deal.
41. I was at a resort in Baja, Mexico, and met a woman on the beach. She had killer legs. Turned out she was a professional dancer. She was there with another guy but gave me her phone number and asked me to call when we both got back to the U.S. We lived in the same city. We made a date, and I took her to dinner. On the drive back to her place she got my cock out and blew me. I didn’t cum then. As soon as we were in her place, I went down on her. We proceeded to fuck, and I have to tell you, she was the wildest fuck I’ve ever had. In truth she was a nympho. As soon as I came, she wanted to go again. After a bit of a break, we did it again. But she still wasn’t through. I was wiped out, but she wanted more. I couldn’t get hard, so she started sucking me like I’ve never been sucked. With much effort she got me hard and I shot a third load, this time down her throat. She still wanted more but I couldn’t do it. Another one and done because she was just way too much for me.
42. I was an officer on the home-owner’s association where I lived. We had monthly meetings. Also on the board was a very attractive woman. After the meeting was over, our group was sitting around watching TV and having a few drinks. She sat next to me and was telling me all about her boring life. Her husband was a traveling musician and was gone too much. I was only half listening to her because I was watching a Dodger play-off game. Then I thought I heard her say “Want to go someplace and fuck?” I asked her to repeat it and she did. When the thing was over, we went to her place and fucked. She was not very practiced sexually. She was shocked when I went down on her. The only person she had ever had sex with was her husband and I guess he didn’t eat pussy. And she was hesitant to suck my cock. I got the impression she had never done that either. Considering how sexually naïve she was, it surprised me that she came out and asked me to fuck her. We only hooked up twice. She was a little too close to home for comfort.
43. During my second marriage, we took a vacation to Asia. During our stay in Bangkok, my wife reminded me that I had this obsession about getting a full body massage which Thailand is famous for. She insisted that I go to it which really surprised me because she was normally very jealous of me and any other women. She even found a place in the phone book and called to get details. I went and it was everything it was cracked up to be. Probably one of my top three sexual experiences. One of the best parts was when I was laying on my stomach and she straddled my neck and gave me a neck massage with her pussy. Then I fucked her. When I got back to the hotel my wife wanted a complete detailed description of everything that happened. By the time I finished, we both were super horny and fucked each other’s brains out.
44. I was at the CES show in Las Vegas. I was really tired and had gone to bed about 11. Somewhere around two am there is a loud banging on my door. I open it to find a business associate who was blind ass drunk standing there with a good-looking woman. He shoved her into my room and says, “Have fun.” I had zero interest in having sex. All I wanted to do was go back to sleep. But because she had been paid, she insisted on having sex. I finally agreed to a blowjob. She gave one of the most vigorous blowjobs I’ve ever had, and she managed to raise a blood blister on my dick that I had to hide from my wife for the next few days until it went away.
45. I had a small side business that only had two employees. One was a very cute little Asian girl. I had the serious hots for her. I took her out a couple of times and tried to fuck her, but she always resisted. I finally figured out what the trick was with her. We would be kissing hot and heavy. I would be feeling her bare tits but could not touch her pussy. Finally, I learned that all I had to do to unlock those legs was unzip my pants and take out my hard cock. For some reason, that did the trick. I probably fucked her six or seven times, but she finally had a problem with me being married and that it was only a sexual relationship between us. When most sexual relationships end, I just move on, but I really hated to see this one end.
46. Then another girl who worked for me at my full-time job and whose looks immediately made me hard, just about drove me crazy with lust. I actually fucked her the first time in my office. I had a private bathroom and I bent her over the sink and fucked her doggie style. After that we fucked everywhere possible. I remember once we went to lunch together and then we fucked in the front seat of my car in the parking lot with other patrons walking by. Nobody noticed us. She really loved for me to eat her pussy. She had an unusually large clit that was very suckable. She finally shut me down because she had serious issues about fucking a married man. Plus, she was looking for a husband and just wasting time with me. She was 29 and I would have been in my early 50’s.
47. After my second divorce, which had nothing to do with my indiscretions, of which I’m very sure my wife never knew about, I took up with a hairdresser who had been cutting my hair. She was recently divorced as well and also knew my now ex-wife. We really just had a fuck-buddy relationship. She would come to my house to cut my hair and we would end up having a sexual marathon. Sometimes they would last all day. She liked to watch me jerk off and one time she brought a girl friend to watch with her. She would blow me or jerk me off and after I would cum, she would rub my cockhead until it was super sensitive. I would try to get away, but she would hang on for dear life and keep rubbing, laughing her ass off the whole time. Every so often she would hookup with a boyfriend and during those periods she wouldn’t fuck me but would jerk me off and give me blowjobs. We lost track of each other when I got married again.
48. I went through a dry period after my marriage and the fuckbuddy girl. So on a whim, I went to a local massage parlor. I hooked up with a cute Korean girl who would jerk me of, suck me off, or fuck me. I used to go every Sunday morning mainly because I drove a very distinctive car and I didn’t want anybody recognizing my car at a sex parlor. Sunday morning was a slow time for the place. I did that every Sunday for a couple of months but then the girl left, and I lost interest.
49. I also found a site online that advertised various massage services. One of them featured a place that provided a full range of Kama Sutra services. I called and made an appointment. I went to the place which was actually a ground floor apartment in a fairly high-end complex. Inside were two extremely attractive 20-something girls dressed like “I Dream of Jeanie.” The one assigned to me was drop dead beautiful. I assumed they were working their way through college. Anyway, I got a super massage and she finished me off with the extended orgasm masturbation technique. I tried to go back a couple of months later, but they were gone.
50. But the same site advertised a man/woman massage team. I had them visit at my house and without going into all the details, the massage led to her jacking me off while I sucked his cock. I ultimately met with just her for a great many more times (for no charge) for handjobs, blowjobs and fucking. A really great sex partner. And a real cutie.
51. Somewhere in the mix, I found another massage therapist who did outcalls. I might have found her on the same site. A very pretty Asian gal who was all business. She basically jacked me off. I was with her a couple of times and we even went out to dinner. She told me she had a doctor client who confessed he wanted to suck a cock but didn’t know how to go about making contact. She told him about me (she knew of my bi interests) and a three-way was planned. The doc was going to pay for everything, and she was going to be there to help out if needed. I thought this was a great plan but at the very last minute the doc chickened out. He claimed an emergency surgery, but she was sure he had a change of heart. Nothing ever came of it.
52. I was then introduced by a mutual friend to a lady who was an interior designer. She had an 18-year old daughter who lounged around the house in a thong bikini and had a body to die for. She looked like a Playboy Playmate. The mother was 45 and at first, she thought I was too old for her but soon changed her mind when I started fucking her like she had never been fucked before. Her words. I would have loved to fuck the daughter who walked in on me when I was shaving in the nude. Mom was at an early morning business appointment. The daughter was wearing a loose robe with her tits and pubes clearly visible. She said she needed something out of the medicine cabinet and proceeded to reach past me to get it. She looked down and said, “nice cock.” She was super competitive with her mother and I knew damn well if I did anything, mom would hear about it. Even though the sex with mom was terrific I knew that her sole goal in life was to get married and I wasn’t into that with her. So I broke it off. She took it really hard but fortunately for her, not long after she did find a guy and married him.
53. I spent a lot of time hanging out on a website called Bianca’s Smut Shack. It’s gone now but it was a super addictive site and I spent way too much time on it. But I did meet several girls on the site. One of the girls and I really hit off and after months of sexual banter back and forth, we agreed to meet. We spent four really great days in a resort city mostly in bed. Not really, as we also did all the tourist stuff. Her thing was she liked to deep throat me and then flick her tongue across my balls. Again, this was a one-time thing because we lived so far apart and going anywhere to hook up required changing planes. We do keep in contact, however.
54. Then another gal I met on Bianca’s also lived a good distance. But she contacted me to say she was visiting friends in my area, but she could spend up to four days with me. The interesting thing about that meetup was I picked her up at the airport and within 15 minutes of arriving at my house, we were fucking like two wild animals. The four days was almost non-stop sex. We even hooked up for a foursome with another couple that I had done a threesome with. She is a super gal and I only wish we could have been together again. We are still in regular touch and are Facebook friends.
55. The third girl I met on Bianca’s was local. And we connected within a week or two of first meeting online. It was an incredible relationship right from day one. Our initial meeting was at my house. She arrived at 9 am and didn’t leave until 11 pm. Except for breaks for lunch and dinner, it was non-stop sex. And it was beyond a doubt the best sex I’ve ever had. I even shaved her pussy on our first date. I can’t remember how many times I came that day. More than six, I am sure. She’s multi-orgasmic so she probably had thirty of forty orgasms. I fell in love that day and we got married about six months later. Unfortunately, it didn’t last, probably due to a huge age difference of 28 years but it was heaven while it lasted. She’s still the only really true love of my life. And not just the sex. She was a really great partner.
56. The divorce really broke me but thankfully I met another gal who literally saved my ass. Our relationship was a lot different than my last marriage. There is love there but it’s not a super-hot passionate love. We have now been together longer than two of my marriages. She is way, way younger than me and I keep telling her she needs to move on to someone closer to her own age. She’s bi and does have a regular girl friend who is younger than she is so maybe that’s all she needs.
57. Somewhere back before I met my third wife (#55) I attended a circle jerk with six guys. One of the guys in the group and I got together for some one-on-one mutual masturbation and a bit of cock sucking. He had a very young girl friend and suggested we do a threesome where she jerked us both off. But no penetrative sex. It was an interesting get-together. She was very shy and although she removed her top, she wouldn’t take off her slacks. She jacked us both and at one point we put our cocks together and she did some C2C jackoff. When it came time to finish us off, she did me first. For a shy little thing she did really knew how to jack a cock. The most impressive thing to me was when I started spurting, she commenced pumping me even harder. And the more I came, the more she pumped. Many women will slow down or even stop when the cum starts shooting. She never stopped. She squeezed out every last drop of semen and I finally had to ask her to quit because it got too sensitive.
58. I took my long-time girlfriend (mentioned in #56 above) to a circle jerk with three other guys. She jacked us all off. Then the next morning I got an email from a woman who had seen my circle jerk ad and wanted to know if she could attend and watch us guys jerk off. She was quite disappointed to learn she was a day late. I told her about my gf attending and so she asked if we could have a threesome and she would watch my gf jack me off. I asked my gf if she was interested. She thought the whole thing was a bit odd but was ok with it. We set up a date for the following Tuesday but in the interim my gf got her period and suggested the next Saturday. I got back to the woman, but she didn’t want to wait until Saturday. She said it had to be Tuesday and could she come to my house to watch me. Again, I had to clear it with my gf. This woman shows up at my house. She had sent me her picture and she was even more attractive in person. Her ground rules were no fucking and really not even any touching. I would jack off while she masturbated with her vibrator. Once we got into action, the rules got bent quite a bit. I went down on her and rubbed the head of my cock on her clit. She wanted me to tit-fuck her and on each upstroke her tongue flicked out and licked the head of my prick. After quite a bit of masturbating she asked me to cum on her pussy. My aim was off, and the first shot flew over her shoulder but the remaining cum shots landed on her cunt. Prior to starting, she had asked me if I could cum more than once and I said I could, but after we both got off, we called it quits. I asked her about a repeat with my gf but she said her itch had been scratched and it was a one-time thing. Also, she said she was getting married the following weekend. The guy she was marrying was a dud in bed but rich. That’s why she wanted to do this little jack-off session. I don’t hold out much hope for that marriage.
In this recital it’s obvious that I didn’t adhere to my marriage vows very well. What can I say? I really love sex and in my younger years that meant more than one woman. But I haven’t strayed on my last two relationships even once in the past 18-1/2 years. However, in both of those relationships, we played around with group sex. Several threesomes, one foursome, and me hooking up for some M2M sex with the full knowledge and approval from both women. With my last girl friend, she even joined me in a circle jerk and jacked all four of us off as mentioned above. Very fun time.
A comment. I have tried to remember every sexual encounter I’ve had but I know I am missing some. Back before my last two relationships when my memory was still good, I had a count in the high 50’s but damned if I can remember them all now. Even after I finished writing this, I came up with sixteen more to reach 58. Not that total numbers really mean anything, but I would like to remember them all just for my own satisfaction.
One last note. Just to show you that even really nice girls love to fuck and can be sluts if they want, I want to make the point that with only a handful of exceptions, most of the women I’ve related above were nice, classy people. No round heels in the bunch. They were all girls or women you would be happy to take home to meet your mom. I know my descriptions make some of them sound easy and slutty. But the truth is that most women love to fuck just as much as a man does and under the right circumstances, any girl will spread her legs for a hard cock.
This addendum to “Eighty-Seven Years of Sex” chronicles my bi activities. I first started exploring that side of my sexual interests when I was in my early sixties. I’ve been able to involve myself with much younger partners because I’ve always looked and acted much younger than my true age. People have mistakenly guessed my age being off by as much as 15 years. Currently at 87 most people guess my age as early 70’s.
59. I first started thinking about some M2M sexual contact when I was between my second and third marriages. I can’t remember the specifics, but I believe my first attempt was via a contact on Craig’s List or it possibly could have been on a masturbation site bulletin board. I really was only interested in some mutual masturbation. Or so I thought. Anyway, I made contact with a guy, and we agreed to meet at a motel room. He turned out to be gay which wasn’t really what I was looking for but by the time I realized that fact, I was too far along to back out. My ground rules for the meeting included no oral which he agreed to. But within ten minutes of stroking each other’s cocks, he was going down on me. And even though I had zero intentions of sucking anybody’s cock, his dick looked so inviting that I returned the favor. We didn’t suck each other off but ended up jacking our own cocks to orgasm. I met him once more after that but frankly it wasn’t what I was looking for, so I moved on.
60. I considered the one-on-one contacts to be a bit risky. Although later experiences proved that not to be a concern. But to avoid the one-on-one with a pure stranger, I arranged for a circle jerk. Again, I think the contacts were made on the masturbation bulletin board. I managed to get five other guys to attend. I don’t think any of them were gay. Just bi-curious like me. We all enjoyed jacking our dicks as a group. After I left, I heard that two or three guys remained at the hotel and some mutual jacking took place. The best part of the group jack was one of the guys interested me as a potential one-on-one. I liked Tom and he really had a nice cock.
61. I contacted Tom about a one-on-one and he was all for it. But it took over a month before it actually happened. I met him in a hotel room. At first it was a bit awkward. We had had the shared experience in the group jack but now neither one of us seemed able to make the first move. Finally, I started taking my clothes off and he followed suit. Once we both were stripped naked, things warmed up very quickly. We stroked our own cocks and then each other’s. I think I was the first one to take the next step. Tom had a really nice-looking cock, and I had a very strong urge to suck it. So I did. We then sort of ended up in the 69 position and he sucked mine. I’m not sure, but I think that may have been the first time he had gone down on a cock. It was only my second. Tom and I had later contact described in #57 above. And I also had a foursome with him and his fiancee, described in #54 above.
62. The original circle jerk had been so successful that I arranged another one. Again, I had six guys including one of the other guys who had been in my first one. This one had a couple of hitches. The first was that one of the guys could not get hard. He kept jacking his soft dick and finally in frustration he pulled up his pants and abruptly left without saying a word. This kind of interrupted the flow of action. Then when we all got back into it, another guy shot his load, and said that he had another appointment, and split. We hadn’t even hardly gotten started. I was pissed about that. Who plans to come to a circle jerk when you only have 15 minutes to spare? The interruptions really messed things up. But once again, the four of us who were left finally got things going again and eventually we all came. It’s fun to watch the expression on guy’s faces as they shoot their loads. I had bought a bag of rags at a local auto parts store and gave a couple to each guy for clean-up. I had everybody deposit their used cum rags in a plastic bag. I didn’t want to leave it in the room so as I was leaving, I dropped the bag of cum-soaked rags in a trash can at the hotel parking garage. One thing about this group jack that was interesting is that after everybody came, two of the guys started playing with each other’s cocks. They both got hard again and proceeded to jack each other off a second time while the other guy and I watched. I was dressed but got my cock out and lazily stroked it while watching but didn’t cum again. Group cock play can be a lot of fun.
63. Some time passed, and I got the urge for some M2M action after my third marriage had ended. I ran an ad in Craig’s List looking for bi-curious guys who were interested in cock-to-cock jackoff. I got a ton of responses via email. I was able to weed out the crazies and obvious gays. By then I had it pared down to about eight guys. Via direct phone I was able to trim those eight to four possibles. My procedure was to set up meetings with each guy at a local restaurant for coffee. We would talk and if either party had reservations, we would part company. One guy was only in town for two days. He was in L.A. on a business trip and was staying at a hotel near LAX and only ten minutes from my house. He was flying out the next morning so despite some reservations about not having a prior face-to-face meeting, I agreed to come to his hotel room. This turned out to be a very pleasant experience. I’m pretty sure it was his first bi experience. The meeting was memorable for me because it was the first time that I sucked a cock to orgasm. I can see why some women really get off on getting a guy to cum down their throat. The taste gets some getting used to but if you can get most of it down your throat it’s not bad.
64. From the same Craig’s List ad for C2C jackoff partners, I did meet a guy at a local restaurant. We hit it off right away. He was married with a teen son but also had a mistress on the side. He was an engineer and a very educated nice guy. We left the restaurant and went to my house and immediately got busy. He had a terrific cock. At least eight inches and very thick. He loved to suck cock and we really had a great time together. I met him two or three more times and then he just disappeared. I remember one special experience. He was laying on his back and I was straddling him with our two cocks pressed together and I was jacking them both off. I could tell he was on the verge of cumming. I was not, so I let loose of my prick and concentrated on finishing him off. He shot a huge load all over his stomach and chest. Then I focused on my rock-hard cock and had an equally voluminous cum load that I purposely sprayed all over his cock and balls. There was something super erotic about spurting my jism all over his still erect cock. I only sucked him to orgasm once. I was just starting to get addicted to taking a cum load in my mouth when he just disappeared. (I did meet a third guy and although he would likely have made a good partner, I didn’t think I was up for more than one guy partner at a time.)
65. Another hookup occurred that was the result of just a stray post on Craig’s List. No advance meeting because I got a comfortable feeling about him over the phone. While we had an enjoyable time jacking and sucking each other’ cocks, it was somewhat of an arm’s-length hookup. I can’t say I ever felt that comfortable with the guy. I want to note here that my interest in a man as a sex partner ends at his cock. I want the guy to be personable and friendly, but my real sole interest is with his dick. No kissing or hugging or any of that stuff.
66. Then there was the experience described in #50, above. This was a guy-girl massage team that came to my house. At one point I sucked the guy’s cock while his partner blew me. He was a nice guy and was able to produce a nice hard-on, but I never got the feeling that he was at all into what was going on. He never came. I was far more interested in the girl, and we hooked up without him many, many times for some really terrific sex.
67. This next experience is a bit out of sequence. It goes back to when I was still married to my third wife, and we had a threesome with a guy I found on Craig’s List. We both took turns sucking his cock. Then I met him a couple of times for one-on-ones. He had a really big cock. He claimed 9-inches. It was definitely something over eight. Then later after I split from my third wife, I had another threesome with him, this time with my girlfriend. Again, we took turns sucking his big dick. I met him after that again for a one-on-one. Funny thing. In the two threesomes I had with him, he wouldn’t touch my cock. But when it was just us, he would jack and suck me off.
68. Time for another circle jerk. By now my third wife was history and I was solidly in a relationship with a much younger girl. That relationship lasted 14 years. But for this circle jerk I talked my gf into participating. She was very reluctant, but I convinced her she could leave all her clothes on and just watch if she wanted. I was only able to get three other guys this time. One of them was the same guy who had been at my two previous circle jerks and the other two were newbies. Both pretty young. In their 20’s. One guy had a cock that was the exact duplicate of mine. Even my gf commented on it. At one point my gf put our two cocks together and jacked them. But I think the guy was a bit put off having his dick pressed against mine. The other guy had a smallish dick. Again, nobody who seemed the least bit gay. Despite the small group, we all had a good time. My gf ended up getting into the swing of things and stripped down once she realized she owned the room. She took turns jacking each guy’s cock and went around the room several times and then finished up by jacking each of us to orgasm in turn.
69. I had one other M2M experience and I was still married to my third wife at the time. With her blessing I attended a circle jerk that was organized by some guy locally. I can’t remember how I heard about it. There were four of us and although the organizer seemed primarily bi, the other two guys were obviously gay. They all knew each other, and I felt like the odd man out. Once the action started, I realized the scene was not for me and apologized and left. My wife took good care of me when I got home.
70. Back between my second and third marriage, I heard about a guy who literally was the master at cock-to-cock jackoff. He had a website called Twin Jets and he held monthly jackoff parties. I contacted him about a one-on-one and I drove to his house. The guy had a pillow arrangement on his bed where the two of us could sit face to face with our backs supported and put our two cocks together. I’ll admit I was a bit put-off by the whole scene and couldn’t get hard. He said not to worry about it. Sure enough, once he started stroking my dick, I got rock hard. The reason I say he was the master was because he had the unique ability to time his orgasm to exactly match mine. Hence the name “twin jets.” While we took turns jacking both cocks together, I deferred to him because he not only knew what he was doing, it also felt better when he was doing the jacking. And sure enough, once I started spurting a load of cum, his semen squirted out of the end of his cock at the same time. Twin jets of cum covered both our cocks and his hands. Later, when I was married to my third wife, I told her about it and that I thought I would like to do it again. She encouraged me to contact him which I did, but I never followed through. Funny thing happened to his website. He held these C2C jackoff parties and then posted pictures and videos of some of the action. Regular attendees at the parties were a father-son team who jacked each other off and also teamed with other attendees. Turns out the son was only 16 and somebody blew the whistle and the site disappeared. C2C is a lot of fun and if you’ve never done it before, give it a try.
ADDENDUM #2, LOST CAUSES
Continuing on, here are a few hookups that never resulted in any actual fucking. We’ve all had these. I’ve had way too many unsuccessful connections that never achieved the ultimate goal. Most of them while in high school. But I made some major mistakes back then. I was so focused on fucking, that when I was unsuccessful, I had no fallback position such as a handjob or a blowjob. Although I’m not sure how many high school girls were giving blowjobs back in the early ‘50’s. I never posed the question so I will never know, at least as far as the girls I was with. I’m only listing a few of the most memorable…or should I say the most disappointing…failures because all the others aren’t even worth talking about.
71. I had a small company with about ten employees. One was a very attractive young girl. She was probably 20 or 21. I knew she was planning on getting married shortly. One day she came to my office and asked to speak privately. She told me that she suspected her fiancée was cheating on her and she wanted to know if I knew of a private detective she could hire. I told her I could look into it but that realistically it would be very expensive to hire somebody to watch the fiancée. The following day I suggested that after work we go to dinner together to talk about it some more. OK, I admit it. In reality I wanted to fuck her in the worst way. So, after a very pleasant dinner at a fairly upscale restaurant where we discussed her situation in depth, we went into the parking garage to my car. That’s when I made my first move with a nice, very intimate kiss. And she responded. We then proceeded to really get hot and heavy with kissing and hugging. I attempted to free her breast but wasn’t having much luck. She kept saying she couldn’t do that. I really wanted to go for her pussy, but she was wearing slacks. Then I attempted a move I had never done before or since. I slid my hand down the back of her pants and right down the crack of her ass. I started rubbing her little butthole and although she lightly protested, I could tell it was turning her on. Then I pushed my hand further and managed to get my fingers in her pussy. I admit that my arm and wrist were killing me because her pants weren’t that loose. I fingered her now juicy cunt and continued to kiss her. My dick was as hard as a rock. But I knew nothing was going to happen in the parking lot, so I drove back to the office where her car was parked.
I invited her to go into the office with me thinking that it would be a waste of time and she wouldn’t go, knowing what it would lead to. But she did go, and I figured for sure that she had decided to fuck me. I know both of us got really steamed up in the car and the ride back to the office was only five minutes, so we were both still horny as hell. We went into my private office and ended up on the floor. We started back up where we had left off and I slid her pants down to her knees where I now had full access to that juicy cunt. I went down on her which surprised the crap out of her. I doubt anyone had ever done that to her. I was lapping her clit and she was writhing around enjoying the crap out of it while squeezing my now exposed cock when we heard the front door of the office open. Oh crap!!! We both scrambled to get dressed but kept quiet as a mouse. About three of my employees had keys but I had no idea who it was. We heard them moving around outside. My office door was unlocked, and I was waiting any minute for the door to be opened. Whoever it was knew my car and the girl’s car were parked outside and they had to be wondering where we were. Then we heard the front door close.
The mood was totally destroyed. All she wanted to do was get the hell out of there and I wasn’t far behind, figuring there’s always another day. Well, there never was. She was scheduled to leave her job in a week or so and that’s what she did. I tried to talk to her about it, but she said what we had done was a huge mistake and she felt terrible about it. So that was that. I never did find out who had stopped at the office. Thankfully nobody ever asked what the two of us were doing.
72. I met a part-time model through my business relationships and used her in some promo material I was doing for the company. She was a real looker. She had been a finalist in the Miss USA contest and was now a college student. Not only was she drop dead gorgeous, she was also very intelligent and a genuinely nice person. If I hadn’t been married, I would have made a serious play for her.
I can’t remember the specifics now, but I made an arrangement for her to come to my high-rise apartment for some casual photos. My wife was in Europe visiting her parents. I had no serious expectations of making out with the model but figured just spending a few hours with her would make my day. We started out with me shooting a large number of photos of her and as time went on the photos got more and more intimate. Nothing really risqué but some nice cleavage shots and close up facials. At one point, her beauty just overwhelmed me, and I kissed her. I was surprised a bit that she kissed me back. That led to a really super-hot and heavy make-out session. Lots of tongue action and we both were getting steamed up. I was really surprised at how truly passionate things got between two people who barely knew each other.
Then a really strange thing happened. This had never happened before or since. But her breath changed. It was subtle but I swear it had the faint fragrance of pussy. It really turned me on. I raised the question of sex…in a subtle manner. I didn’t just say “Do you wanna fuck?” But the signals I got back were very positive. I knew she was going to fuck me.
Then the damn phone rang. It was the front desk advising me that her boyfriend had arrived to pick her up. I had no idea that’s how she got to my place. He was about an hour early from the time she told me that she had to leave. She told me later that he came early to beat the traffic.
So that was the end of that. I knew she got caught up in the moment but probably wouldn’t do a repeat. Plus, my wife got back a few days later and I never even bothered trying to get the model gal to meet up with me again. She went on to marry the boyfriend and they’ve been together 50 years.
73. I had a long-time employee who was leaving because she and her husband were moving out of state for a new position he was taking. She was one of my favorites. We had a long running teasing relationship but with us both married and working together, we were ok with keeping it above board. On her last day with my company, I took her to a celebratory lunch. We both had a bit too much to drink, and on our way back to the office, I got a wild hair up my butt and pulled into a local park. We sat and talked for a bit, and I could tell she was receptive to my possible advances. So, I did. And things got very steamy. I was sucking on one of her titties while she stroked my exposed cock. We both really wanted to fuck but were afraid to go that far in a public park. I couldn’t go to my place because my wife was there. I thought about a motel but was worried about what the staff would think if we were gone that long. I should have asked her to blow me or jack me off but didn’t really think about it. Stupid me. Back to the office we went. And that was the last time I ever saw her.
74. Here is probably the craziest one. I had a girl who worked for my company. We had flirted off and on for at least a year. It was one of those relationships where I knew that if I pursued it, there would be a pay-off. Finally, one day she was in my office and complained about a sore neck. I gave her a neck massage. Then I couldn’t resist myself. Standing behind her I slid both hands up under her sweater and was shocked to feel two bare breasts. No bra. She didn’t need one. She turned her head and kissed me. But that was all that happened because anybody could have walked in my office at any time. I immediately detected that the time was right and so I asked her out to dinner. And she said yes.
I was separated from my second wife at the time, but we were temporarily still living together until the house was sold. She was leaving to go back east to visit her best girlfriend in the next couple of days.
The girl and I went to dinner at the local TGI Friday’s. After we got back in the car, we started going at it hot and heavy. I was tempted to fuck her right there in the car and I knew she was willing. But figured I could wait a day until my wife was gone and have a proper sex blowout at my house on a big comfortable bed. I talked to her about coming to my place two days later and doing the naked hot tub thing as well as finishing what we had started in the parking lot. She was all for it.
I think I must have had a permanent hard-on for the next two days just thinking about getting her naked. On the day that she was due to meet me at my house later that day, I got a call from her. She can’t make it. She told me that she’s moving in with Larry. I said, “Larry who?” When she told me, I really couldn’t believe it. Larry was one of my best friends. I had no idea he was even seeing her. He had never mentioned it. I never did tell him how close I came to fucking his new girlfriend. The relationship didn’t last long, but once she was free, I was locked up with a new flame.
75. Another one I will always regret is described in #52 above. If I had known that I would be breaking up with the mother in a couple of weeks, I would have gone ahead and fucked the daughter, who I have to tell you had one of the best bodies on a woman I’ve ever seen. Of course, she was only 18 which helps explain the great body and firm natural tits. I have always regretted not fucking her when I had the chance.
There have been others that I regret. More than once I have passed up doing the actual deed and putting it off for a better set of circumstances, only to never get another chance. The moral of that story is “Strike while the iron is hot!” Or maybe that should be said “Strike while the dick is hard, and the pussy is wet.” The truth is there will likely never be a better time than right now.
That’s it for now!! Happy jacking, sucking and fucking.