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Interview With an Extraordinary 87-Year-Old

I had originally intended to interview someone of advanced age who is suffering the usual difficulties with aging, finding out that person’s attitudes about sex, current sex life, and so on. However, this guy turns out to be really exceptional in many ways. I believe you’ll fall in love with the fellow in this interview. – Jeremy

How old are you?


How is your health?

Great. Only issue of note is high blood pressure but that’s more or less under control by meds. And due to some sports activity that I do, both knees need some extra support with braces. But I only wear them when doing my activity. The rest of the time it’s not a problem.

What are your sexual preferences and interests?

Primarily women. Later in life I got bi-curious. Started with some mutual masturbation. I was 60 or 61 at the time. Never had any M2M contact as a teen like a lot of kids did. I discovered masturbation when I was about 10 or 11 from climbing the poles on swing sets at school. Of course those were just dry orgasms and I thought I had discovered something that nobody else knew. I had my first true sexual experience when I was 15 with a very clumsy attempt to penetrate a 13-y.o. girl who actually came onto me. The first time I tried it, I ejaculated on her before I could get it in her pussy. The following night we tried again successfully. But once I fucked a girl, I was totally hooked. The crazy thing is, within two weeks of losing my virginity, I fucked two more girls. It was pure happenstance. I was in was total heaven.

I managed to get more than my share of pussy in high school. By the time I was a senior I had a regular girlfriend (who I later married) and we fucked every chance we could get which was at least four or five times a week. Keep in mind that when this was going on, I was 17 and she was 16. My only regret is there were quite a few high schoolers I dated who wouldn’t fuck and I was so focused on getting laid that settling for a handjob or a blowjob never even crossed my mind. I’m sure I missed out on a lot of handjobs back then. Not so sure about blowjobs because I don’t think there was a lot of that going on in the early ‘50’s with high schoolers. But I did eat my first pussy when I was 17. My girlfriend didn’t want me to do it. She thought it was disgusting until I got my tongue on her clit. Then she thought it was a great idea. I really can’t remember if she blew me while we were still in high school. After I went down on her, she might have, but I’m damned if I can remember.

One thing that you need to know about me. I’ve always looked much younger than I am. As I got older that helped me hook up with younger women. Even now, at age 87, people who don’t know me guess my age as late sixties.

Back when I was about 60, I hooked up with a woman who was 45. At first, she didn’t want to date me when she found out my actual age because she thought I was too old for her. But before I knew it, she was talking marriage. The best thing about that relationship was she had an 18-year old daughter who lounged around the house in a super skimpy thong bikini. On top of being drop dead beautiful, she had a body that belonged on a Playboy centerfold. One time when I slept over at their house, the mother had left early for an appointment with a client. She was an interior decorator. I was in the bathroom nude shaving when the daughter walked in wearing a loose bathrobe open in the front with her tits and pubic hair clearly on display. She said she wanted to get something out of the cabinet. As she got whatever it was she wanted, she looked down and said, “Nice cock.” I was speechless. I knew she wanted to fuck and I was dying to give her what she wanted. But she and her mother were very competitive, and I knew that if I fucked her, she would somehow let her mother know. So, I didn’t do anything. Which turned out to be a huge mistake because a few weeks later I broke up with her mother anyway. If I had known the relationship would be ending that soon, I would have fucked the daughter and lived with the consequences.

Do you have any kinks or fetishes?

No, not really. Well, I do have a mild foot fetish but I am so damn particular in what I find attractive that very few women actually have what I consider really good looking feet. I’ve had a few women masturbate me with their feet and that’s pretty hot. And I love really good-looking athletic legs. Not overly athletic but well formed with nice definition. A restaurant I go to regularly has a waitress with killer legs. Literally the best I’ve ever seen. She obviously knows it because she always wears short shorts. I go there at least twice a week, mainly just to look at her legs. I’ve told her how much I admire her legs. She told me that some of the patrons refer to her as “the legs girl.” She’s a runner which has a lot to do with the way her legs look. I would guess her age at about 25 but she has a 14-year old son so obviously she’s older than 25.

Do you still get horny as in your younger years?

I think the answer is ‘yes.’ Frankly it’s a bit difficult to totally think back and remember the degree of horniness when I was younger. But if it’s diminished any over the years, it’s not apparent to me. I still fantasize lying in bed at night before going to sleep about fucking some cutie I saw during the day. There is a high school girl who walks by my home office window every weekday at 8 am and 4 pm. I try to be there to see her. She’s tall, probably 5’ 10” with long blond hair. She frequently wears shorts and has long attractive legs. Not that it would ever happen, but I fantasize about fucking her brains out. Since she’s a high schooler she is likely only 16 or 17. Coincidentally, she just walked by as I was typing this. Then there is a very attractive girl who works at a small family restaurant I frequent. With her looks and her body, and her obvious maturity, I had assumed she was a 20-something. I was shocked when she told me she was only 16 and a sophomore in high school.

How have your attitudes about sex changed over the years?

As stated earlier, I was always true-blue heterosexual up until I was about 60. In fact, the whole concept of sex between men repulsed me. The idea of a cock in my mouth was unthinkable. But some time back when I was in my thirties or forties, I saw a video of two young guys performing cock-to-cock jackoff. At the time, despite my homophobia, I thought that looked really hot. But I never took it past just watching that video until much, much later. But after my second marriage ended, I had a long dry spell on being with any woman other than some fuck-buddies and some visits to the local massage parlor. That’s when I started thinking about hooking up with somebody for some mutual masturbation. It’s interesting that many, many years after seeing that C2C jackoff video I finally got to do it. In fact, I have done it with at least five or six different guys.

The most interesting was a guy who specialized doing C2C. The amazing thing about the guy was he was able to time his ejaculation to exactly match yours. It was extremely erotic to see two cocks held tightly together, both cumming at the same time. He had a website called “Twin Jets” but it’s long gone now. He also held C2C jackoff parties and featured photos and videos on the site of guys doing C2C jackoff. There was a father/son team that came to his parties and they were featured on the site but somebody blew the whistle because the son was only 16 or 17 and his site was taken down.

The M2M stuff actually started with me organizing a circle jerk because I was too worried about hooking up with just one guy. I had safety concerns and also just felt that a group thing might be a better introduction. That turned out to be the right way to get started. Then I hooked up on one-on-one sessions with a couple of guys from the group. My ground rules before any of these encounters was jacking off only, no oral. The idea of sucking dick turned me off. Well, that didn’t last. The first guy I hooked up with went down on me within the first five minutes of having our cocks out. He’s sucking me and I’m looking at his erect dick and the damn thing looked so good I went down on him. We finished off with handjobs. When I left the meeting, I had terrible guilt feelings about what I had done. But within a day or so I had rationalized the whole thing in my mind and came to the conclusion that I was still the same person I was before giving a guy head, and that all I had really done was just had some fun. Didn’t hurt or affect anybody else. In reality I expanded my own sexual horizons.

After that I sucked a few dicks, but it took me a while to work up to sucking a guy to completion. I finally forced myself to do it just to see what it was like. It wasn’t bad at all like I thought it might be. The secret is to have the guy’s cock as far down your throat as you can manage so most of the cum passes right by your taste buds. I’ve only taken three loads in my mouth, but I enjoyed it. There is a certain feeling of accomplishment when you can make a guy cum from sucking. Some guys are incapable of ejaculating from a blowjob.

I have no interest in any kind of emotional connection with another man. I don’t want to kiss him or even hug him. I never walk down the street and see a guy and try to imagine what his cock looks like or what it would be like to have sex with him. All I want is some fun cock play. And now that I’ve done some of that kind of thing, I realize that there are a lot of otherwise straight guys who feel the same way. But with women, it’s the exact opposite. I want emotional involvement. I want to be attracted to the whole woman, not just her tits and pussy. For me to get the full level of enjoyment possible, there has to be that emotional link between us.

That’s not to say I haven’t had sex with a woman without the emotional attachment. I have, but in many instances, it was a case of it’s there, it’s available, she’s attractive, so why not? Later on in this Q&A you will read about some very quick and dirty sex where emotional involvement was nowhere to be seen.

Over my lifetime I have had sex with somewhere around sixty women. Many of them involved emotional attachment but obviously many of them didn’t.

As far as any M2M sex goes, it’s only a rare sometime thing for me. I still prefer woman, but every once in a while, I get the urge for something different. At one point I was occasionally hooking up with a guy who was a great partner. Although we met on Craig’s List, amazingly he only lived less than a mile away. He had a really nice big cock and despite being married plus a girl-friend on the side, he loved to suck dick. Unfortunately, after about four hookups, he disappeared. He no longer answered any emails, and I never knew his actual address or phone number.

Married M2M partner’s excellent cock. Sorry to lose touch with him.

My cock and my partner’s much larger cock. OK, I need to clarify this.
Because I am farther down in the pic, my dick looks pretty small next to his.
There really isn’t that much difference although his is notably thicker.

When is the last time you had sex with another person?

Unfortunately, it’s been a while. I was having regular sex with a long-time girlfriend. We were together for 14 years to be exact, but when I moved across the country about 18 months ago, she stayed behind because of family, friends, and a job. I haven’t made any hookups since moving for several reasons. Covid is one, but the other is I like my women young, or at least younger than me. As an example, my first wife was one year younger, second wife was ten years younger, third wife was 28 years younger, and my long-time girlfriend is over 44 years younger. Woman my age do not interest me. I realize that’s probably sexist and shallow but that’s the way it is. My chances of hooking up with anybody at this point in my life that I would want to have a sexual relationship with is probably nil. I have thought about maybe making some M2M connections and now that Covid is on the wane, I plan to pursue that.

Was it as easy, vigorous, and enjoyable as sex in you earlier days?

Absolutely. If you are referring to the last time I had sex. Maybe even moreso now that I have so many years of experience. Sex for me in the last few years has been almost more about pleasing my partner as opposed to my own pleasure. That in itself is a form of pleasure.

Do you miss the frequent sex you had in earlier days?

Yep, definitely. If I had a regular partner who was as into it as much as me, I would probably be having sex every day. More on that subject with an answer to a later question.

How do you spend a typical day?

I can’t get too specific without people who know me reading this and realizing who I am. I’m semi-retired but still work a few hours a day for some clients. But recently I’ve decided to start a new business and most of my day is devoted to getting that launched. I spend a lot of time in front of my computer and always manage to look at several sexual sites. I have some favorite girls on Chaturbate that I like to watch and also the videos on XNXX are great jack-off material. ProWank and Solotouch are also great sites to get the juices flowing. Evenings are spent reading and watching tv. I manage to read about a book a week. I buy used paperbacks from I also participate in some competitive sports but again hesitate to mention exactly what they are. I generally find time to jack off at least once a day, sometimes more.

Do you have favorite ways to masturbate?

Not really. I guess I am kind boring in that respect. I went through the stages of lubing up my cock and also sticking a finger up my ass but have kind of gotten away from that in the last few years as it’s a bit messy. My experience with a finger up the butthole is to have it well lubed. Shove it in and out while masturbating and just as you start to orgasm, pull the finger out swiftly. At least for me, that seems to highten the orgasm sensation.

I used to do a lot of edging primarily to generate huge cumshots but one of the meds I take for prostate issues has totally limited the amount of cum that I produce. Unless I do a very extended masturbation session, sometimes no semen is produced at all. If I do edge and keep it going for a long period, I might produce six or seven large clear droplets. Fortunately, the orgasm is still the same. Or at least I think it is. No way to really compare other than memory which isn’t always accurate. Frankly of all the downsides of old age, losing my ability to spurt impressive streams of cum is the most disappointing. On of my claims to fame is I could shoot great distances. One of my girl-friends really got off on seeing how far I could spurt my cum. She would even get out a tape measure and measure it off. This was after edging but I consistently would fall just short by an inch or so of five feet. Even a usual cumshot could be good for a couple of feet. Unfortunately those days are gone forever.

Recently, more as a lark than anything else, I bought one of those masturbation toys that has a jelly sleeve that rotates around your dick while you pump it up and down. It’s fun and it feels pretty good. Even though for me cum cleanup is minimal, you have to use a generous amount of lube with the toy so there is that to clean up.

What kinds of things do you fantasize about while wanking?

I usually watch a video on XNXX. And what interests me and gets me going changes frequently. I went through the CFNM (clothed female, naked male) period. Recently I have been watching a series of videos where the girl makes the guy cum strictly by frenulum contact with her fingers or tongue. I particularly like the scenes where after the guy cums, his partner takes his cum covered cock in her mouth and sucks it clean. My last wife used to do that, and it was extremely erotic to watch her do it. Although there are very few videos that feature it, I also like to see the woman take a washcloth and lovingly wipe the guy’s cock clean. I don’t know why, but I find that very hot. It may have something to do with a period I went through where my only sexual outlet was a local massage parlor. I had a steady Korean girl who took care of me every time I went there. She would masturbate me, suck me off, or fuck me. And she always took a warm, wet, washcloth and very thoroughly wiped my cock clean afterwards. I used to go there every Sunday morning for about two months. Then I met the gal who became my third wife and that ended the massage parlor visits. Haven’t been back since.

Do you have any physical limitations due to your age?

Maybe about what you would expect for a 65-year old man. Certainly not one who is 87. But now that I think about it, I’m probably even physically more active than your typical 65-year old. I did notice back when I was having sex with my girlfriend that the marathon fucking sessions were a bit more work than they used to be. When I was with the 45 y.o. with the sexy 18-year old daughter, and I was 60, we both were into extended fucking. Our sessions typically lasted 45 minutes to an hour. I would pace myself to keep from cumming but she would have several orgasms during that period. Unfortunately, I’m pretty sure I could not do that today.

Any sexual limitations?

No, not really other than it takes me longer to get a hard-on. And if I am sufficiently aroused it gets about as hard as it ever did. But I would say most times when I jerk off, it’s only about 90% hard, which is all that is needed. I keep some Viagra on hand and if I feel like having an extended jack-off session I might pop half of a pill which allows me to stay harder longer than I might without it.

I remember back when I was in my 50’s and even in to my 60’s, I could stand naked in front of the bathroom mirror and will myself to get erect without touching my cock. No way is that possible now.

Would you say you are happy most days?

Absolutely. Without going into details, over the years I have made a lot of money and lived at a very high level. I’ve been with a lot of beautiful women, had lots of material things, traveled the world and had many, many experiences that many people just dream about. I’ve led a very, very full life and even though those days are over, I have no regrets.

Have you lost anything that you valued with age?

I don’t have the energy that I had just five or six years ago. I mostly have associated with people younger than myself and instead of me having trouble keeping up with them, the opposite has been true. But whatever it was that gave me that extra something that most people my age do not have, it’s slowly slipping away. Which is to be expected. Father Time can’t be stopped.

You’re healthier than many people at the same age. To what do you attribute your success?

I have no idea. I’ve never smoked, and I stopped drinking in my late 50’s. But I think it’s mostly genes. My sister is three years younger than me, and she doesn’t remotely look like an 84-year old. My dad died young from lung cancer. He was a three pack a day smoker and that was back when nobody knew smoking killed you. My mom lived to 89, but had heart issues, which I don’t have, fortunately.

Do you have a bucket list?

Not really. There really isn’t much left that I would like to do. Let me qualify that, there’s really not much left that I could do, even if I wanted to. For example, I always wanted to visit Machu Picchu. But it’s quite challenging to get there and at a high altitude that would probably be more than I could handle coupled with the climbing. Back when I was at the peak of my earning power and heavily into boating, I probably had some of the best times of my life on my boat. I would love to have another boat and if my new business takes off like I expect it to, I might actually have a boat again. But when I recall all the work, effort, and money that went into keeping a boat, having one doesn’t seem like a great idea, so maybe I will pass on that. There is something called the Freedom Boat Club where you pay a monthly fee and have the use of a boat any time you want. It won’t always be the same boat, however.

Do you have any regrets or things you’d do differently if you could?

I had a couple of business relationships that if I had handled them differently, I would be in the lap of luxury today. I’m not hurting by any means, but degrees of wealth are relative. The only other real regret I have is that my last marriage didn’t last longer. She was by far the best sex partner I ever had, and it ended all too soon, but it was her decision and there was nothing I could do. In a way, it was my fault. Before we met, she had previously been married but led a somewhat ordinary existence. Then she married me, and I showed her what life could really be like and she realized how much of life she had missed out on. And decided that there was much more she could experience if she wasn’t tied down to just one man. She actually told me this. And it wasn’t just the sex. I loved her more than any other woman I have ever been with. When my first two marriages ended, I was ok with it and ready to move on. But the third one crushed me. I went into deep depression, lost a lot of weight, and really felt I had no reason to live. But then I met my future long-term girlfriend and she literally saved my ass.

What do you look forward to?

At this stage of my life, I really don’t think too far ahead. I guess my one hope is that this new business is successful so that I can leave more to my kids than I would be able to otherwise. I might leave something for my long-time girlfriend for putting up with me for 14 years and livening up my sex life at an age where for most men it’s a distant or forgotten memory.

Do you have a greater fear of sickness or death than when you were younger?

I don’t think in terms like that. Life is what it is. I just try to stay as healthy as I can and what happens beyond that is out of my hands, so I don’t think about it. I assume that there’s not that many more years left for me. But I can’t worry about it.

Do you still vividly recall your early sexual experiences?

A few of them. Oddly enough, the ones I remember the most vividly are the girls I wanted to fuck but never did. One girl in particular stands out. She was 19 and I was 32. We got into a really hot and heavy petting session and we did everything but fuck. I went home with the worst blue balls of my life. I knew in my heart that I would get a second chance at her but for reasons out of my control, it never happened. I still jerk off imagining what it would have been like to fuck her. Not that it would have been all that different, but it was still a regretful lost opportunity, of which there have been many.

Thinking back to really early sexual experiences, I can clearly remember having them but unfortunately some of the details are missing. OK, I know I fucked her, but did she blow me first? Did I go down on her? Those important details are sometimes lost.

I do have a vivid memory of one experience. This was a temp employee who worked for me. She was also only 18 years old. We had a couple of petting sessions that got really steamy, but she claimed to be a virgin and was saving it for her husband. Finally, she decided after all that horsing around, that she wanted me to fuck her. I think it was because she knew it was her last week at the office before returning to New York where she lived with her dad. Anyway, the memory that is so vivid, even though it was over 50 years ago, was at one point she was holding my stiff cock and rubbing the head of it all over her face. I can’t remember any other woman ever doing that and it was incredibly erotic. Then she sucked it and that of course led to me fucking her. No way was she a virgin. She was one hot fuck.

I’ve had other really crazy experiences that I can barely remember. One in particular was during my first marriage, my wife and I had a party at our house. By this time our marriage was really over. Lots of friends of friends were there who I barely knew or in some cases had never met. One really attractive gal kept giving me the eye and at one point I pulled her out the back door into the night and started kissing her. In no time flat it went totally out of control and we walked into a wooded area behind the house, and I fucked her. I don’t remember if we did it standing up or laid on the ground or what. I never knew who she was or who she was with. Never saw her again. My excuse on that one was we both probably had too much to drink.

Shortly after that in the final days of my first marriage we went to a Halloween party at some friend’s house in our neighborhood. I was sitting on a couch in the rec room when this gal in a cat costume sat down and started talking to me. My wife was helping in the kitchen. The girl had a mask on but I could see she had a nice body and appealing eyes. It’s hard to describe this but the costume she had on had panty hose with short tight elastic pants over them. But the way she was sitting, the pantyhouse actually pulled the pants away from her body and I could literally look down and see her pussy lips protruding through her pubic hair. I’d had a few drinks so I told her, “I can see your pussy.” She replied, “How do you like it?” I told her I would love to get my tongue in it. After some more witty conversation, I took her hand and said, “Come with me.” It was a split-level house, and we were on the lower level. I got her up to the entryway and tried to get her to go upstairs to a bedroom, but she wouldn’t go. I pulled her into the hallway coat closet, and we went at it hot and heavy for a few minutes. I somehow got her tights and pantyhose pulled down below her knees and kind of bent her over and entered her pussy from behind. The whole thing was so fucking sexy and crazy that it only took a minute or two of thrusting to drop a load deep in her cunt. How nobody missed us or realized what was going on was a miracle. Never knew her name or who she was with, if anybody. Never saw her again either.

Now these stories go directly against what I said earlier about needing some emotional involvement with a sex partner. Obviously, that didn’t happen in these instances. This was just pure raw sex. But that’s fine. I think everybody needs some of that kind of sex because it’s exciting and forbidden. Forbidden sex is very appealing. And when it’s a perfect stranger, it’s really good for the ego. To know that you have the kind of attraction to another person that allows them to fuck you and to hell with any consequences.

At what age do you feel you were the most sexually active?

That’s easy. I married my third wife when I was 67 and she was 39. I suspected it wouldn’t last because of the age difference but I was head over heels in love with her and figured I would get what I could out of it. We had met online on a sex site and after a lot of emails and phone conversations we agreed to meet. For some reason she offered to come to my house. On our very first date, she came to visit me at my house about 9 am and didn’t leave until 11 pm. I can’t remember how many times we had sex, but it was beyond description. The best sex ever.

Third wife gets one of her daily fuckings. Sure miss her.

Once we were living together, she had to be fucked every single day, and on the weekends, two or three times a day. In the three and a half years we were together, it never got old. On weekdays she had to get up earlier than me to go to work. We had a terrific sex session every evening once we went to bed. Then Saturday morning I might wake up to her giving me a blow job which led to a full-on fuckfest. To be repeated again that night. Same on Sunday. She loved for me to cum, but primarily inside her. To her, any cum that occurred outside of her body was wasted. Sure, she jerked me off from time to time but mostly it was me cumming deep inside her pussy or down her throat. In the latter stages of the marriage, we even had a threesome with a guy I found on Craig’s List. That was a really fabulous experience. She got off on seeing me suck the guy’s cock. In fact, we would take turns sucking it, handing his cock back and forth like a lollypop. And I got off on seeing him pump his big dick in her pussy. When I was younger, the thought of my wife being fucked by another guy or her sucking his dick was unthinkable. But for us, a threesome was just a really fun thing to do. I was amazed at how turned on I got with the experience.

Threesome guy penetrates my former wife.
Although not apparent in photo,
his dick was at least 8” long and she really got off on it.

Wife jacks my cock and threesome guy’s cock. Heaven.

After the marriage was over, my new girlfriend and I eventually got around to a threesome with the same guy and that was equally exciting. My girlfriend was also a terrific sex partner but because we didn’t live together, it wasn’t as frequent as when I was married. One of our highlights was I arranged one of my circle jerks and brought her along. She was hesitant at first but once she realized she owned the room, she took turns jerking off all four of us.

Long time girlfriend grips my cock and another guy’s cock.

I penetrate my girlfriend’s sweet pussy.

Can you briefly tell us about some of your wildest sexual exploits?

Where to start? One that sticks in my memory is back around 1970 I took some friends to the notorious area of Baltimore that’s loaded with strip clubs. One that we went to was the “2 O’Clock Club,” which was famous for featuring the famous stripper Blaze Starr. This was after she had moved on or retired, however. There was one stripper who was young and incredibly attractive. I couldn’t take my eyes off of her. She must have noticed because after her set she came over and sat down with me. The goal for the strippers is to get you to buy them expensive drinks that are likely not even alcoholic. But instead of angling to get me to buy her drinks, she just wanted to talk. I was terribly flattered because it was obvious that she was attracted to me. But what was even crazier is under the table she unzipped my pants and got my cock out and proceeded to jerk me off. Once I shot my load under the table, she kissed me and said she had to get back to work. I never bought her a single drink.

Then there was one time in high school where my regular girlfriend and I had temporarily broken up. I invited this extremely cute girl to a party that was all made up of kids from my school. This little gal was super sexy for a high-schooler. After mingling in the party for a half hour or so I was hungering to get my hands on that cute body, so I invited her to go back out to my car. You could drive legally in my state at 15 and I had my own car. So once in the car, things got really hot and heavy and before long, I’m sitting in the passenger’s seat and she’s straddling me facing me with my cock buried deep in that sweet teen pussy. She’s bouncing up and down on me as our classmates are wandering around outside. I don’t think anybody noticed what was going on but doing what we were doing more or less in plain sight was really hot.

Then on a trip to Cabo in Mexico with a fuckbuddy who was totally uninhibited, we had rented a Suzuki Samurai which was open a like a jeep, and as we were driving from Cabo San Lucas to San Jose Del Cabo, we passed several trucks loaded with workers in the back. The part that was special was she was giving me a blowjob while the workers were cheering as we drove past. Then we had a late dinner in San Jose Del Cabo and as we walked down the deserted main street after dinner I had to pee. She pointed to a doorway and told me to go there. I replied, “Only if you hold it for me,” Which she did, but that led to her jacking me off right on main street as a few cars drove by. And finally on another night we were lounging on our suite patio around midnight when she decided she wanted to fuck. She climbed on top and started banging away when we heard voices. I said something and she told me to shut up and fuck, so I did, as two couples strolled by about ten feet away. They stopped and watched for a few seconds and then walked on.

Same gal brought a friend to my house one time and had me jack off while they watched.

girlfriend tongue on glans
Fuckbuddy girlfriend licks my cockhead.
She got off on playing with my dick.

While I was in college (an all-male school) I took a high school girl on a picnic. One thing led to another and in the back seat of the car, she got so wet that she literally left a puddle on the seat which was fortunately vinyl. I had a bit of trouble finding her opening but finally, among all the juice, it slid right in. She said, “You’ve got it in the wrong hole.” My first taste of anal sex. I quickly found the right hole.

Speaking of anal sex, I did have one girlfriend who preferred it. She said it felt better than vaginal sex.

One other first for me was I had hooked up with a girl, again on a porn site, and we had a number of sexy email and phone conversations when she offered to come spend four days with me. Which turned out to be four days of non-stop sex. The capper was when she told me she was a squirter. Of course, I had heard many stories and seen videos but I never believed it could actually be done by a woman. In the videos I always assumed it was just pee that came gushing out. She folded up several towels and sat on them and got out her Hitachi Magic Wand. She said she could only do it using a vibrator. She proceeded to rub the wand up and down over her clit and after a few minutes, this liquid started squirting out. It was clear so I was pretty sure it wasn’t pee although some pee is nearly clear. So to be sure, I tasted it. I don’t know what it was, but it was definitely not pee. That was many years ago but we are still Facebook Friends to this day although she has been in a committed relationship for years and we never did anything after those four days.

Squirting girlfriend was also an excellent blowjob artist.
Here she sucks down a load of my cum.

During those four days I arranged for a foursome with a couple who I had done a threesome with. In the threesome, the girl just jacked off her boyfriend and me. However, she had a very delectable looking pussy and I really looked forward to fucking her in the foursome. According to her boyfriend, who I had met in one of the circle jerks, we were going to be free to fuck or suck whoever we wanted in the foursome. My gal was looking forward to performing C2C jackoff on us two guys. She had never heard of it before. She also wanted to fuck him and of course I wanted to fuck his girlfriend. Well, the first mistake we made was us two guys put our cocks together and my date started jacking us off. In hindsight, we should have worked up to that. The guy’s girlfriend really got her nose out of joint when my date touched her bf’s cock. He realized it and immediately lost his hard-on. The rest of the time together his girlfriend spent all her time trying to get him hard again. Although he never did get fully hard, somehow she managed to get him to cum. In the meantime my date and I were sucking and fucking each other like no tomorrow while the two of them watched. I was very disappointed that I didn’t get to fuck the other girl. But my date made sure I was well taken care of.

What advice do you have for younger people?

Young people are going to have sex come hell or high water. My only advice is to make sure it’s safe sex and don’t get pregnant. My first wife was pregnant when we got married. If she hadn’t been, I would never have married her, because by that time we had been together for two years and I knew she wasn’t right for me. But back then, the only path was marriage. I stuck it out for nearly nine years. And don’t get married or stuck in a relationship at a young age.

Here’s one tip to the guys. If you are in a hot and heavy session with a girl you are trying to fuck, but she won’t give it up, unzip your pants and take out your hard cock. My experience is that the majority of times I’ve done this, it’s worked. At the very least you might get a handjob or a blowjob out of it. One time I did it with a girl who was being unusually stubborn but amazingly as soon as she got a look at my erect penis, she didn’t say a word but went down on me and blew me. She actually sucked me until I came and swallowed. I did eventually fuck her.

Whatever you do, never force a woman to do something sexually that she doesn’t want to do.

After relating all these various sexual adventures, were you turned on?

As a matter of fact it really did get me excited. I had been stroking my cock off and on during the various stories that I related and when I got to the end, my prick was quite hard and I decided to jack off. I was rewarded with an unusual (for me) fairly decent cumshot. Instead of the usual nothing or at most three or four squirts of cum, this time there were seven or eight. What comes out isn’t really cum. It’s just a clear liquid in fairly large droplets. But I was very pleasantly surprised by the result.

Also see 87 Years of Sex – a list compiled by this same person of all the women he can remember with whom he had sex.

Here’s a picture of our extraordinary gentleman when he was only 72 years old.

1 thought on “Interview With an Extraordinary 87-Year-Old

  1. great story. loved the photos.

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