I was a late bloomer, well at least later than most of my friends. In high school I was multifaceted, a jock, a nerd, a stoner. I could hang well with any crowd, although I was somewhat social awkward. Part of the reason is that I am a very emotional and passionate person. I always had trouble with 'falling in love' too easily and was told that I wear my emotions on my sleeve, whatever that really means.
At seventeen, I had barely been involved with anyone for longer than a few weeks and even then I did not spend much time in any type of sexual situation, let alone really 'made out' with anyone.
It was at a party one night that I met my soon to be girlfriend and also the one that I did most of my experimenting with. She was also socially awkward, although mainly with the opposite sex. She was beautiful, although throughout a good part of her childhood had the wonderful bad skin that a lot of the teenage population was plagued with.
She was irish, with the pale skin, dark hair and blue eyes, in addition to the redhead irish look these are my two favorite types. And of course our mutual friends helped set us up that evening. We talked and laughed and when it was time to go to get cigarettes for our mutual friends, she drove and I sat in the front seat.
When our friends went into the store we talked about our lives and became interested in each other.
It was a few weeks later that I found myself in her basement with my hands down her pants feeling her wetness. That was the first pussy I touched and I found myself wanting to taste it, so in that teen age awkwardness we ended up in a 69 position on the couch, barely able to keep from falling off, but there I was licking my first pussy.
We did this for quite some time after that day, she would give me a blow job and I would eat her out, but sex was still out of the question. I don't remember ever coming during those times but I had no idea what I was really doing and she was just as inexperienced.
When we finally decided to have sex, I rushed off to the pharmacy to purchase the condoms and we tried to think of a place to finally have sex. We decided on my house although the details are vague after 23 years. I remember a blanket by the pool, and decided that would not work. Then going into my house and using the couch. There was one time where I proceeded to call out, 'its in' although that was definitely not the first time we had sex.
The hard thing for us was the fact that I am fairly large in girth and many women have complained about my size. It may not be the longest but definitely is pretty wide.
After that we pretty much tried every variation we could think of, standing, sitting, her on top, reverse cowgirl, doggy, missionary and what became our favorite, spooning. We were of course two horny teenagers that could not get enough of it, even in the back seat of my honda civic hatchback, which is no small feat since I am 6'2".
In college we ended up at the same university and continued dating. The first year was tough, although she had a roommate that was never there and ended up dropping out after the first semester and she ended up with a single. There were a few memorable experiences, one of my favorites was when I walked in to her room after classes and she dropped to her knees and took my cock in her mouth as I ran my fingers through her hair.
Our second year in college was where most of the experimentation took place. She had moved off campus and I was living in a fraternity house. All of her roommates were pretty and she had some great parties. A few of which we ended up all naked together. While none of us had sex with anyone else it was still quite a turn on when everyone was walking around naked.
It was one of those nights that I had my tongue in her ass for the first time. I had her on all fours and was spreading her labia and flicking my tongue along her clit. At one point I ran my tongue from her clit all the way to her asshole. She squirmed and moaned quite loudly so I continued. My tongue would play for a minute at her ass as her moaning would get louder and louder. I could tell she was about to come and focused more closely on her clit. She came very loudly and collapsed in a heap on the bed.
That was the initial point where I realized I love playing with her ass. Many times after that we ended up in the same position but I was still uncertain whether I could actually have anal sex with her.
Until one night, when she decided to stay in my room at the fraternity. We had both been drinking a little bit and ended up in my loft. I was fucking her in the spoon position when I pulled out and put my cock on her asshole. Slowly I applied pressure and asked her if this was okay. She replied to just go slow, and so I entered her. I pushed a little bit at a time until it was almost all the way in and relaxed for a minute so she could get used to it. It was of course extremely tight and I wanted to savor every bit of it. So I reached around and stroked her clit while just remaining deep in her ass.
After a little bit I pulled out and pushed back in slowly until she could take more of it. She was still really tight and after a few minutes of going back and forth I decided to just go back to my cock in her pussy, until we both came in a wild frenzy.
We tried many more times after that and while we were never all that successful we still had a lot of fun doing it. At one point we discussed the possibility of really making it work, but it always seemed to be something that we would do in the midst of other things.
We broke up not too long after all of this, mainly due to the fact that I was having fun sexually but emotionally I was not present in the relationship. Although a few years later when we were both single we started the whole friends with benefits relationship and that was a fun time. We even had sex in the gondola at Squaw Valley to emulate the classic Hot Dogs movie of the 80s, and practiced the art of mutual trimming of the pubic region in the Circus Circus hotel in Reno, Nevada.
Experimentation at that time was a lot of fun. There were times that I wish I could have tried more with her, she seemed as adventurous as I was when it came to sex. She talked about trying to have a threesome at one point but we never were that serious about it. I think that was when I had a dildo in her pussy while she was sucking my cock. She said the sensation was overwhelming.
Unfortunately we grew apart again and like before I was mostly to blame for it. But my experimenting was pretty much lost after her, most of my partners have been fairly vanilla or just not that into sex. There have been times where I have experimented with a girl in the virtual world, basically mutual masturbation on webcam, but that is the furthest I have gone in experimenting with anyone else.
And of course the mutual masturbation was a lot of fun, however there is a lot more desire of other pursuits that I would like to fulfill at some point. Years ago, my wife was willing to experiment to some extent but mostly it was talk and never did we try anything out of the ordinary. Mostly sex in different places but never unusual sex.
I consider myself to be somewhat kinky. I like the imagery of BDSM and would love to practice, but I also know my limits while being in a committed relationship. I would love if my wife would be interested in experimenting but currently sex has been a bit few and far between, so I am left to my own devices.
How do I bring up that I want to be fucked in the ass by her using a strap on when I barely even touch her now? I have put my finger and tongue in her ass in the past but that has always been met by 'What do you think you are doing?'
The desire to play has led me to sites that cater to such things, but as always I do not think I would ever play with anyone without her approval or in the perfect scenario her being with me. To me sexual experimentation is a lot more fun with someone you completely trust. Someone that would not judge you to be weird or have strange ideas about sex. Unfortunately for me I think that ship has sailed. Guess I will always have my fantasies.