Copyright 2014 by the author.

Introduction

This is the 100% true, (to the best of my recollection) story of the second and third time I had sex. The names have not been changed to protect anybody.

The True Story of My Second and Third Time

After my unexpected deflowering at the Salt Lake City airport, my life reverted back to its normal, sexless condition. I didn’t get the job in Tacoma, so I headed back home to Kansas City and moved in with some high school buddies. We had plenty of good times, parties every weekend filled with booze and weed, but none of the girls that hung around ever showed any interest in me.

The next year, I got restless again and really fucked up by joining the Army. What a mistake that was. I’m not really a follower, and that’s what they’re looking for in the military. I had always been a free spirit, or as my dad said, “Lazy”. To make matters worse, I ended up being stationed in Alaska. Aside from being one of the most expensive places in the USA to live, it’s insanely cold most of the year, and when you’re not freezing your balls off, you’re being eaten alive by swarms of hungry mosquitos. Add to that the fact that I was living on a military base with ten thousand other men, there was no chance I was going to beat those odds and catch one of the few women that were available.

I couldn’t wait to get out and go back home. After my unremarkable military service, (Please don’t thank me for my service. It was in the mid ’80s during the cold war, and it was one giant waste of time) I went back to Kansas City and moved in with a good friend who was going through a divorce at age 21. And I thought my love life sucked.

I landed a decent job at a small company that manufactured electronic thing-a-ma-jiggers. I worked in the pencil pushing department, keeping track of engineering drawings and specifications, parts lists and the like. Real exciting stuff, but the pay was decent and I was actually good at what I did and seemed to earn the respect of the engineering staff.

I was still single, so my mother decided to try her hand at matchmaking. She set me up with a girl she knew from her job with the government.

I went out on a few dates with Myra, and although I liked her and I thought she liked me, it was hard to tell. She was very quiet and reserved, and it’s difficult to describe, but the word ‘slow’ fits her best. Not slow in the sense of being dumb, she was a smart enough woman, but everything she did seemed like slow motion. She spoke slowly, moved slowly, everything was just slow.

Myra was fairly tall for a woman, around 5’9” and a little heavy, but not obese. Plump is a good word to describe her. She had a decent face, long brown hair and was about my age.

We went out on a few dates, and everything seemed to be going okay. We kissed, but there was no passion, and around our third or fourth date, we ended up at her apartment on her couch. Now remember, if it hadn’t been for a fluke occurrence when I was 17, I still would’ve been a virgin, so to say I was inexperienced for my age would be an understatement. I decided to try to put my hands under Myra’s shirt and fondle her big fat titties, and when I did, she offered no resistance, but didn’t give any sign she enjoyed it, either.

I was so horny, I was determined to keep pushing until she put on the brakes and stopped me. She never did, and a while later we were in her bedroom naked. I had taken off her clothes and my own. She didn’t help, but she didn’t resist either, so I kept pushing.

I had seen enough pornography to know that women sometimes spoke or even moved during sex, but not Myra. She was the coldest of cold fish I’ve ever encountered, and even though she was only the second woman I’d had sex with, it was boring and tiresome trying to get a reaction from her.

I can’t very well describe her as willing, but she did what I wanted without any hesitation. At first, I was on top and we did it missionary style, then I had her turn over and tried doggie style for the first time. She never really got wet, damp is about as far as it went, and it was somewhat painful for me and I can’t imagine it was any better for her. She was obliging if nothing else, but it was so awful that I didn’t even orgasm, after a while I got bored and simply quit.

The strangest thing about it all was that I really liked her, and before we had sex, I had seriously considered the possibility of a long-term relationship with her. I thought we might one day get married and have some very large children. When I left the Army, I was 6′ 5” and a svelte 225 pounds, so I figured between Myra and me, our kids would have been huge.

I never would have believed it, but I finally found a woman who I actually liked, and who was willing to have sex with me, and I had no interest in doing it again. Call me a bastard, but I broke up with her shortly after that and never saw her again. The conversation I had with my mom when she asked why I wasn’t dating Myra anymore was very awkward. Try telling your mom that one of her co-workers is lousy in bed.

Back in the dark ages of the late ’80s, there was no internet, so you had two options if you wanted to meet someone. You could hang out in bars and meet alcoholics, or you could join any number of social groups. My parents divorced when I was young, and they had both at one time or another belonged to various social groups. My mom joined a group called PWP, which stood for ‘Parents Without Partners’ and I remember my dad met a woman through a club for tall singles.

I was already a member of the high IQ society, Mensa International, and noticed in their monthly newsletter that they had singles meetings. I thought it would be interesting to meet a highly intelligent woman, so I went to a meeting at a private residence in an affluent suburb. When I got there, I was a little disappointed because I was by far the youngest person at the gathering. Most of the crowd was baby boomers, probably at least ten years older than I was.

I decided to stay at the party anyway and ended up meeting the president of the local Mensa chapter. Her name was Karen and she was twice my age. I was 22 and she was 44. She was nice and not too bad looking for her age, but I wasn’t looking at her as a potential sexual partner, she was old enough to be my mother. In fact, she was exactly the same age as my mother.

We chatted for a while, just casual small talk, and discovered we had something in common. We were both of Scottish ancestry. My mother’s grandparents had emigrated from Scotland in the 19th century, as had Karen’s.

Karen invited me to the local highland games being held the next weekend, and I agreed to go, thinking it was a Mensa group outing. When I got there, she was waiting at the gate by herself. I thought it was just poor attendance, or that maybe Karen and I were the only Scots in our local Mensa chapter, so I didn’t think it was odd that we were the only ones there. (I know, I know. For a member of a high IQ society, I was fucking clueless.)

If you’ve never been to a highland games, it’s a typical ethnic festival. Vendors selling ethnic food, travel agents selling package tours to Scotland, tailors selling custom, hand-made kilts in your family tartan. (Talk about expensive!) We avoided the haggis and walked around, seeing the sights.

I knew growing up that my mother’s family was from Scotland, but I knew very little of the culture, so I was having a good time, discovering my roots. I didn’t realize it, but there were actual games at a highland games, including one very interesting competition called the “caber toss”. A caber is a big, heavy log, taller than the men who tossed it. The competitors would lift up the caber and balance it upright in front of them, then they would squat down and thrust the caber into the air, with the goal being to throw it end over end. I think. I’m still not sure what the hell it’s all about, but I do remember it involved large men wearing plaid skirts thrusting an even larger pole up in the air. Large men… Skirts… Thrusting… Pole… Sounds sexy, doesn’t it?

I honestly don’t remember why I followed Karen to her townhouse after the games were over, I’m sure food was involved, because I still didn’t realize I was on a date. After dinner, we were in her living room and she practically threw herself at me. I was surprised, but quickly came around to the idea. At least she threw herself at me with a bit of passion. I must have shown my surprise because Karen immediately pulled away and began apologizing. She said she was sorry for thinking I would be interested in a woman as old as she was, and told me she would understand if I left and never wanted to see her again. She didn’t cry, but I thought she might, and by that time, the small amount of blood that had been circulating around my brain was rushing to fill my cock.

Since the little head had taken over my thinking, I took Karen in my arms and kissed her deeply and passionately. She was wearing baggy cotton shorts and a t-shirt and before I knew it, she was nude on the couch next to me. I quickly stripped down and followed her upstairs to her bedroom.

If you’re expecting a story about a 44 year old woman with the body of an 18 year old, you’ve come to the wrong place. Karen had the body and face of a 44 year old. She was at least a foot shorter than me, easily 20 pounds overweight, and not in a good way. Her tits were on the small side and she had a bit of a gut, but she was naked and willing and that was enough for me at that time. She was more than willing, she was eager, and to me, that was a new and exciting experience.

She was on her back on the bed as I lay down beside her. We kissed, and to be honest, it was weird. I was a very young 22 year old and I was making out with an old woman who had crows feet, a wrinkled neck and saggy tits. Her only redeeming physical quality was her pussy, and that was spectacular. She had a big, beautiful cunt with big, fat, meaty lips and a big swollen clit, and did she ever get wet. As soon as I touched her big soft pussy, my hand was drenched with her juice.

She wasn’t on the pill, and I thought she’d make me use a condom, but I didn’t have any on me because I didn’t expect to be in bed with a woman twice my age that day. She surprised me by pulling a small white tube from her night stand, telling me it was spermacidal foam. She opened the package, inserted the thing in her pussy and filled herself up. Seconds after she tossed the applicator in the trash I was buried in her cunt. She felt fantastic, so hot and wet and soft and smooth. For the first time, I actually did fuck a woman long and hard and deep. Karen was moaning and whimpering as I pounded her into the mattress. I can’t say if she came or not, I was too inexperienced to know what to look for, and I was so wrapped up in how I was feeling that I didn’t really care. I could tell she was enjoying herself, and I loved hearing her tell me how big my cock was, and how good it felt inside her.

Like I said in my other story, I’m not much longer than average down there, but I’m pretty thick, and Karen told me over and over how good it felt.

After drilling her sloppy old cunt for a good long while, I erupted inside her, and kept going as I filled her with my cum. Afterwards, I collapsed on her chest for a few minutes before rolling over to her side. I was completely and utterly exhausted, but it was by far the best sex I’d had, and as good as I’d imagined sex could be.

My first time was over as soon as it began, my second time was achingly dull, but there with that mature woman, my third time was absolutely fantastic.

As we laid side by side in bed, catching our breath and enjoying the after effects of some stupendous sex, she reached over and took my soft cock in her hand. She whispered in my ear and told me my cock was so big, big like the cabers we had seen tossed around earlier that day. From that moment on, she always referred to my cock as my caber, and although I thought it was silly, I didn’t say anything. I may not be the smartest guy at the local Mensa chapter, but I am smart enough not to argue when a woman compliments my manhood.

Since I was so cool and avant-garde back then, of course I smoked clove cigarettes. Karen didn’t smoke, and she didn’t want me smoking in her house, but she said she liked the smell of clove cigarettes, and said she’d join me while I went outside for a smoke.

We went downstairs where we had left our clothes on the floor, but I suggested we go outside nude. Karen looked shocked, but she turned off all the lights and followed me out to her back patio. It was pitch dark, but her patio wasn’t fenced in and it was exciting to be outside naked with her. She kept her hand on my caber, gently stroking me while I smoked, and we whispered and giggled about how naughty it was being naked outside on the patio. That became a regular thing for us that spring and summer whenever the weather was warm enough.

After I finished my smoke, we went back to her bedroom and fucked like rabbits. It was Saturday night, and I had no place to be until Monday morning, so I stayed the night, sleeping with a woman in my arms for the first time.

One of the few similarities this story has with all the fictional erotica around here is that I was truly in my sexual prime, and so was Karen. We could fuck until we were exhausted, rest up for an hour or so, and go right back at it. I filled that old woman with so much cum that first weekend, it was still leaking out of her Monday morning when she went back to work.

Did I mention that she worked for the local public school district, and that part of her job was monitoring the high school’s ‘gifted’ program? Her job put her in contact with gifted children every day, and nearly every night, she had a young gifted stud of her own giving her a good, hard pounding. Looking back now it does seem strange, especially when you consider how young I looked back then. I’ve always had a baby face, and at 22, I could have easily passed for 16 or 17.

We had a rather odd relationship as it turned out. The difference in our ages was so obvious, neither one of us wanted to go out in public on regular dates, so most of the time we spent the evening at her townhouse fucking each other’s brains out. We never had oral sex except for one time when we showered together I did lick her pussy briefly. She never sucked my cock and we never fucked doggie style. She said she had some ‘issues’ about a man being behind her, but I didn’t press for details because I liked fucking her missionary so much, and I wasn’t interested in hearing a sad story about her past.

As much fun as the sex was, that’s all it ever was to me. I didn’t love her and I knew I never would, she was just a nice, convenient place to park my dick whenever I wanted. Eventually I started getting bored with her company and stopped going to her place every night. As our fuck sessions became less frequent, she got more and more clingy, and seriously stalked me. I saw her drive by my house several times, and sometimes she’d leave cards or flowers on my car while I was at work. That creeped me out, but I did like it when she left a pack of clove cigarettes under my windshield wiper with a note saying she missed me.

I didn’t have any other women in my life, so I still threw Karen a bone a few times a week for the next year. Just because she turned into a creepy stalker, my cock didn’t see any reason to stop fucking her.

As had happened so many times before, I started getting restless and wanted to make a change. My roommate at the time had some family in Seattle, WA, and his cousin had a job as a bouncer at a strip club there. I had never worked as a bouncer, but I knew my size would help me get the job, so without thinking about it too deeply, I quit my job and packed everything I owned into my 1971 Cadillac hearse and drove to Seattle. I never saw or heard from Karen again.

I never got a chance to thank her for giving me the greatest gift I’ve ever received. She gave me the confidence I needed to lose the shyness that had made it impossible for me to approach a woman. Karen showed me that I wasn’t undesirable and unattractive, and that I had something women wanted. She made it possible for me to finally leave the shy, awkward teenager behind when I moved to Seattle, and for that, she’ll always have a special place in my heart.

The End.

Stay tuned for my exciting adventures at the strip club. I promise there’s a lot more sex. A lot.