Eccentricities

All of my stories are true. Most happened in the 1970's when sex was still relatively safe and the sexual revolution was in full swing.

I have been blessed in my life to have had sex with over 300 women. It's not that I'm a big Romeo or anything. Sure I've been told I'm handsome and in my younger years I was an ex-Marine, 6' and 175lbs, blue eyed with brown hair. I kept in shape and was always friendly. But the times were right and I was in the right place. I worked my way through college as a Security Guard and ended up as Head of Security for a luxury high rise apartment complex in a close suburb of Boston. The complex was two towers with nine floors in each tower. It was filled with young college girls and mostly young affluent couples and families. I worked the night shifts on most occasions. So I got to see women in a non threatening environment on a daily basis. I was often there as they came home after a bad date or a fight with their boyfriend. You couldn't ask for a better situation.

One thing that I have learned is that the world of sexual behavior is indeed a wide one. "Different strokes for different folks" is a very true statement This story chronicles some of the "sexually eccentric" women I have known. By that I realize that they were eccentric to my sense of normality but that doesn't make them not normal, just different from me.

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The Girl Who Couldn't Fuck

I had known Michelle very casually in High School but really not well. During college I worked at a Hospital as a security guard at nights and she was now a nurse there. She was really an attractive woman at 5'5" tall, brown shoulder length hair, and a great body. She was also very friendly and funny. Casual conversations and the boredom of the night shift eventually lead to sexual adventure. Michelle sucked me off and I went down on her in empty patient rooms, stairwells and even elevators. We never had intercourse just oral sex and at first I attributed that to the fact that it's just easier to do oral than intercourse in such furtive circumstances.

But then we started to date outside of the hospital and I discovered that there was another reason. Michelle was deathly afraid of fucking. She really wanted to, but when the time came, she just froze. She asked me to be patient and help her to overcome her fear. I really liked her and she gave great head so it was easy to agree to try. So we mounted a concerted effort to get my dick into her pussy. I got a buddy of mine to give me the keys to his cabin in New Hampshire one weekend and Michelle and I headed up determined to end her situation.

Once we arrived I started a fire in the fireplace. I opened a bottle of wine and we settled down in front of the fireplace. We kissed and caressed. We touched and we pleasured each other orally. When we were ready she told me not to stop no matter what until my dick was inside her pussy. She was nice and wet from the earlier attentions and I figured that this would be a piece of cake. I was wrong. She lay back and spread her legs. I got between her legs and moved my hard cock between her pussy legs. I pushed forward expecting to sink into that wet pussy. But the gates were closed. Michelle tensed up so much that I could not get my cock inside that pussy! And the harder I tried the tighter it got and the more upset she became. What had been a soaking wet pussy dried up. We tried several more times that weekend but it was not to be done. Sure we had oral sex to orgasm but when it came time to shove it in, the gates would not open.

Well, we ended the relationship soon after. I got reassigned to other places and there wasn't much point in it. I have often wondered if Michelle ever managed to overcome her fear and if she ever got fucked.

The Girl Who Never Knew Me

Chickie was a hot looking red head who lived in the building where I worked as Head of Security. She was in her mid twenties but lived there with her mother. She was usually friendly when I saw her but not overly so. One night she came home very drunk and when I asked if she was OK she told me that she had gone out with some girlfriends to celebrate her birthday. I wished her a happy birthday and she got very friendly and when I asked if she got everything she wanted as presents she blurted out "I got everything that I wanted but a good fuck!"

I offered to remedy the situation. Since we couldn't go to her apartment we went to the Community Room which had stuffed chairs and a sofa and a door that locked. I fucked her there until she was totally satisfied. Once we were done she went on up to her apartment and I went back to the security desk in the lobby.

Every time I saw her after that she pretended like it never happened. I never said anything to her about it just figuring that she was either embarrassed or so drunk that she didn't remember. Shortly after that the building management fired the security company I worked for, but hired me as Head of Security, basically I would hire and train all the guards, schedule them and I got a nice raise and a free two bedroom apartment. Sweet!

I was only in my new apartment for about a week when there was a knock on my door one evening. When I opened the door it was Chickie, once again drunk. She threw herself onto me and as I pulled her in to the apartment she made it clear that she wanted a rematch. I was happy to oblige and spent several hours fucking her into oblivion. Afterward she went off to her apartment. Once again, any time I ever saw her she acted like nothing ever happened. Over the next several months this routine was repeated. When she was drunk she showed up at my door expecting me to fuck her. And afterward she would never acknowledge that anything out of the ordinary existed between us. After a while this got to be a bit annoying. I actually started to turn her away but she still kept popping up at my door.

One time she showed up and I was hanging out with my buddy Joe. I let Chickie in but told her that I was too tired to fuck her. I thought that my buddy Joe would probably be up to it. Boom! She took Joe up on the offer. We actually ended up both fucking her at the same time and she even let us DP her!

Well this continued for over a year. Many of my male and female friends who happened to be around at the right time ended up fucking her. She would do oral, anal, eat pussy, lick ass, threesomes, more somes. Basically when Chickie was drunk she would do anything. It only stopped when Chickie finally moved out of the building. But never during the entire time when she was sober did Chickie show any indication that she knew me other than being the guy at the front desk.

The Girl Who Was Afraid To Cum

I met Patty when I worked as a security guard at a company that manufactured high speed computer printers. She worked in the accounting department and was easily the most beautiful woman in the company. She was 24 years old, had shoulder length black hair, big, beautiful dark eyes, thick sensuous lips and a body that made every guy watch her wherever she went. I always made a point to stop by for some casual conversation when ever I could reasonably justify it. She often stopped by the security desk on her way home for a few minutes of discussion. Over the months I learned that she had a long term boyfriend but only really saw him on Friday nights. I was dying to figure out a way to get this woman naked.

One Saturday night I drew the midnight to 8:00 AM shift. It was usually pretty boring because no one was there, the place was locked up tight and alarmed and I just had to make a round of the building every hour. About 12:30 someone buzzed the back entry door. Curious, I disabled the alarm and opened the door to find Patty standing there! She had obviously had a little too much to drink but she asked if she could hang out and talk for awhile. Apparently she had a fight with her boyfriend. "Come right on in." said the spider to the fly.

I let her in and locked up the door, reset the alarm, and took her to the security office. The office was adjacent to the loading area where they packed and shipped the printers. I had a radio playing and Patty and I sat and talked. She asked me if I wanted to smoke a joint and I agreed. She whipped a pre-rolled doobie out and we smoked it. After that Patty got really touchy and flirtatious. It didn't take long before I made my move and was kissing those full luscious lips. It also didn't take long to get her clothes off. Some women look better with their clothes on but Patty wasn't one of them. Naked she was truly beautiful. Her breasts were full B-cups but firm as hell. She had dark puffy nipples that stood full and erect. Her waist was tiny, belly flat and she kept her black pubic hair nicely trimmed. Her pussy was bright pink with full swollen lips glistening with her excitement. Her ass was firm and rounded. My favorite thing is to eat pussy. I'm a fanatic about it. I had to taste this woman!

The only problem was there really wasn't a place to lie down in the Guard Office. Thinking quickly I spotted a pile of packing boxes in the loading areas. They were thick card board stacked flat, ready to be assembled for packing. Perfect! I led Patty over to the stack and helped her up. She lay back on the stack and spread her legs for me. I got down between her legs and got busy. I swear that she tasted like honey! She had sweet, pungent, woman juice. It was a cunt connoisseur's dream. I sucked and licked and fingered that beautiful pussy to my hearts content. I could not believe that I was finally getting some of this fine woman. There was a pool of her juice sinking into the card board under her ass. She was really enjoying the attention and urged me on.

I knew that I was getting her close to orgasm. Then the game changed. Just when I thought she was going to go over the edge she started pulling at my hair and squirming out from under my tongue. If I tried to get close to her pussy she pushed me away. I didn't push the issue and she calmed down enough that I was able to fuck that hot pussy and ended by shooting off between those gorgeous lips of hers. But when ever she seemed to be getting ready to get off she would pull away. We finished up and I let her out and on her way home.

She continued with her steady boyfriend but we hooked up quite a few times afterward. But it was always the same in that whenever she got close to orgasm she would literally fight me off of her. One time when she had a few drinks in her I asked her about it. She was reluctant to talk about it but did mumble something about her Catholic Girl upbringing. I fucked Patty until the company we worked for went out of business but I have wondered over the years whether she ever managed to cum.

The Girl Who Only Wanted It In The Ass

Wendy was a sexy blond woman around 23 years old when I first met her at a friend's pool party. We hit it off right away and I ended up with her telephone number and the promise of a date. We did dinner and a movie and I felt lucky to get her back to my place afterwards. She wasn't shy about my advances and it wasn't long before I had those C-Cup tits in my mouth and hands. Her pussy was wet and ready when my fingers finally found their way there. She eagerly took my cock into her mouth and worked me just fine. But no matter what I did that night, I couldn't get an orgasm out of her. I ate her and fingered her for literally hours that night but she just never reached orgasm. I found this a bit concerning because I rarely had encountered this with a woman.

On our second date we had the same experience. Great sex except Wendy didn't cum. Finally I asked her about it. She shyly told me that the only way she could achieve orgasm was through anal sex! Now, I have never been a particular fan of anal sex. Not necessarily turned off by it but I was much more interested in pussy or a nice hot mouth. Once the confession was out I got some hand cream and we got down again. Finally I was between her legs working some cream into her ass and onto my dick. Once she was well lubed I pushed the head of my dick into her ass. She didn't hesitate or make a peep and I slipped in easily. I fucked that ass hole for all I was worth and Sandy came several times during the session. I was relieved that I had discovered her secret because she deserved to have it her way after all the pleasure she had given to me.

I ended up fixing Wendy up with a buddy of mine who had a major fixation with anal sex. They were a great match and dated exclusively for years.

The Girl Who Loved the Sky

To tell you the truth Kathy wasn't the type of woman I was attracted to. She was fairly plain looking and had a little too much padding in the butt than I liked. But she was witty and very outspoken. She and her roommate Jill lived in the apartment complex where I was Head of Security. One night I was at a club in Boston and they recognized me. I ended up giving them a ride back to the apartments afterward out of common courtesy. Kathy sent her roommate on ahead once we got back and then looked right in my eyes and said, "I would really like to suck you cock."

Well, I had enjoyed a couple of drinks, didn't have any specific plans for the rest of the night and really like blow jobs, so I agreed to it. Kathy asked if we could go up on the roof to do the deed. The roof was 9 stories up, had a sun deck and normally was locked at night. But as Head of Security I had keys to everything. So up to the roof we went.

The view was really great from the roof. The building was in a near suburb of Boston and there was an unobstructed view of the Boston skyline. As soon as we got through the door Kathy dropped to her knees and unzipped my pants and fished my cock out. She looked right up at me and said that she loved to suck cock and then she got to work.

I have to admit that this dumpy plain girl really knew how to suck cock. She alternated from licking and sucking to rubbing the head all over her face. She pulled her blouse open and then rubbed my cock over her small tits. She had me ready to cum in no time. But I figured what the heck; maybe I should give back a little. So I had her stand, take off her panties and bend over the retaining wall of the roof. I lifted her skirt, rubbed my cock head up and down her slit to wet it, and then shoved it into her very wet pussy. She had a perfect view of the city skyline while I fucked her from behind and rubbed her clit with my finger. After she had a nice orgasm I pulled out, pushed her back to her knees and came in her mouth.

Well, on many occasions afterward Kathy would call or come by the security desk and ask me if I wanted a blow job. She always insisted on the roof. Once she actually put together a picnic basket and took me off to a secluded area in a local park. We had lunch and then I screwed her doggie style on the blanket right out in the open.

The closest we ever came to having sex indoors is when she talked me into screwing her roommate Jill. Kathy masturbated in a chair while watching us.

Many years later Kathy actually invited me to her wedding reception. At the reception I was seated at a table with 10 other guys. During the course of the evening we all figured out that we had shared outside sex with Kathy at one time or another.

The Girl Who Loved Her Dogs

Elise had everything going for her. Good looks, nice body and she was a registered pharmacist. She would come by the Security Desk to talk while doing her laundry and after several times we ended up going into the locked rental office and having sex on the sofa there (Head of Security has keys to everything!) I was pretty excited about continuing to have some fun with her at our next meeting.

She invited me to dinner at her apartment and as soon as I was in the door I was greeted by two small, white, yapping poodles. I like dogs and figured that was no problem until one of them jumped up and nipped me on the thigh about 1 inch below my dick. Elise just laughed it off and we had dinner. After dinner I offered a joint but Elise didn't approve of illicit drug use and gave me a bit of a hard time about it. I chalked it up to her profession. We smoothed things over and headed to the bedroom for some fun.

Things were going fine, I had her clothes off, and she was sucking my cock while I played with her tits. The dogs were still scurrying about though. I suggested that maybe we should lock them out of the room and got a scornful look and an interruption to the blow job. I tried to forget about the dogs and just enjoy the sex.

Finally I had her wet and ready and climbed on top of her and pushed my cock into her wet pussy. I started to give her a nice fuck but then felt something wet and raspy on my balls. Looking over my shoulder I realized that the poodles were on the bed with us and one of them was licking my balls while I was fucking Elise. Frankly, I found this a bit distracting and stopped the action. Elise shooed the dogs off the bed and locked them out of the bedroom and administered some oral attention to my cock to get me interested again. The dogs whined and scratched at the door and made such a distraction that neither one of us could concentrate on the sex.

I excused myself to go to the bathroom while she dealt with the dogs. While in there I peaked in her medicine cabinet and couldn't believe the number of prescription drugs! One bottle was filled with liquid and labeled "Tincture of Opium." "And she's giving me a hard time about smoking a joint?" I thought.

Back to the bedroom we went and the dogs were once again back in the room. Elise got frisky and just told me to ignore them. I finally got back into the situation enough again to end up in the delightful position of lying between her legs and sinking my cock into her nice wet pussy. This time there were no distracting sensations on the balls. Enjoying her hot pussy I quickened my pace and she was clearly enjoying the sensation as much as I was. She came within a few minutes and I continued to slam into her. Suddenly I was aware that the dogs were up on the bed again. I tried to ignore them and just kept slamming into that good pussy. I was getting close to my orgasm when I felt the dogs leap up on my back. So here I was propped up on my hands, nailing that pussy like a steam piston with two poodles riding on my back! It was too ludicrous to ignore and once again I became too distracted to even maintain my erection. I rolled off of Elise and the dogs went tumbling off my back and off the bed whining and yelping. Elise angrily protested my "brutal treatment of her babies." That was the last straw for me. I put my clothes on and said my good nights. On the way out I stopped by the bathroom and made sure to dip the two joints I had in the bottle of the "Tincture of Opium."

The Girl Who Loved Aural Sex

My late wife had been dead for about a year when a woman who worked for me suggested that she arrange a date with a friend of hers. Ellen was 38 years old and had never been married. I saw a picture of her and figured I'd go for it. The arrangements were made and a date set.

My first impressions of Ellen were pretty good. She had short brown hair and green eyes. She had a very nice body. I picked her up at her house and we went to dinner. Over dinner I got the first warning sign. Ellen confessed that she was a recovering alcoholic and so only ordered sparkling water with dinner. I ordered a glass of wine which she eyed suspiciously. She had been off the sauce for about three years but still went to AA meetings once a week she told me. I changed the subject fairly soon.

Ellen confessed to going to the gym daily and talked about her stenography business and her family. All of this was pretty normal and dinner went pretty well. We drove back to her place and even though she didn't invite me in, we did have a pretty nice French kissing session in the car before she went on in.