Filed under: Sexual History | Tags: boy toy, Having Sex, older woman, Sexual History
In looking at my current situation, I have to look back at my life. Mostly this is to see if I can see a pattern or to see if I can see possible reasons for my current situation.
I had the pleasure of opening up a nightclub where I was king of the world for a couple of years. A few months into it, a band required a limo to take them everywhere and I met the owner of the company. She was very attractive, auburn hair, and about 19 years older than I was. She asked me for my number and we started dating pretty quickly. She had a large house that she shared with her seventeen year old daughter. The sex was pretty amazing and she would help me make her orgasm – that was very important for her. I would go to fancy parties with her, out to dinners, and other places where it ended up I was just being ‘shown’. I guess I was her boy-toy. It felt good and I didn’t mind. That relationship ended on a weird note where she said that a business partner of her ex-husband was involved in the mob and if anyone ever asked for her, I was NOT to say that I knew her. She really did just disappear.
SP8 Recap: Being a tool was actually fun. I would have men come to me and ask me who I was and ladies who would also ask where I came from. Having almost more in common with her daughter was a bit strange. Having her daughter walk in on us was stranger. It was weird how it ended – I have often wondered where she went.
Filed under: Uncategorized | Tags: Friends, Having Sex, older woman, Sex Observations, Sexual History, smooth chest
In looking at my current situation, I have to look back at my life. Mostly this is to see if I can see a pattern or to see if I can see possible reasons for my current situation.
Another coworker and I started seeing eachother. She was ten years older and had a young daughter. She lived out of the city quite a bit but we would have fun going to movies, to dinners, and hanging around her house. Her body-type was pear shaped – ‘normal’ on top but really large in the hips and large thighs. I was given a lot of crap about her shape by everyone at work and one day it had just gotten to me. That was shallow. I was also a bit freaked out answering questions from her daughter. She was given a rash of crap from her aged friends as well. The thing I remember most about her was that she loved my ‘smooth chest’. I wish she could see me now!
SP4 Recap: Age and body shape doomed this one.
Filed under: Sexual History | Tags: first time, Having Sex, older woman, Sex Observations, Sexual History
In looking at my current situation, I have to look back at my life. Mostly this is to see if I can see a pattern or to see if I can see possible reasons for my current situation.
My senior year (12th grade) I started working as a cashier at work to get more shifts. I worked with the head bookkeeper who was about twelve years older than me. Drinking was always involved after work – and she would invite some select employees to her house or out afterwards. She would start giving me ‘mix-tapes’ – cassette tapes of music that was pretty suggestive at the time. One night, during an after-hours inventory or cleaning – we were both pretty drunk and we started kissing. We kissed and rubbed eachother until daybreak in the office. It was pretty steamy from my point of view. She was older than me, kind of like a hippie. She was thin, not large breasts – attractive but as a young guy with all those other women around – not my first pick. She had definitely chosen me. She was told from the others that I worked with that I was a virgin. We talked a lot about it and one day made ‘the date’ where we knew what was going to happen. I remember it, just a little less each year I get older.
Alcohol was definitely at play, I think we both needed it. Me – as I was scared, her – probably just in case she was busted for contributing to the delinquency of a minor. I remember that from making out and rubbing, that I had cum already in my underwear. She told me it wasn’t so bad, we’d just have to wait a bit. We continued and she actually put my penis in her mouth [SCORE]. Yes, I got hard again and we started to make love. Hell, it was sex. I was scared shitless. I kept falling out, going too fast, not concentrating. In my mind, I was scared that I would pee inside her. All said and done, it was messier than I had expected – but damn fun!
We continued seeing eachother but as most relationships go, I thought that we were spending too much time together. News of our relationship was ‘out’ at the restaurant and I became fair game for the girls my age. Given the choice of an older lover and a younger one – I broke up with the older. This was the instance in life that I coined the observation that a relationship had better potential if you could look at the other person naked without laughing to yourself. She had breasts that I remember as banana shaped. Just the profile is what I was thinking of, but I still remember them fondly. It was hard to have to work with her still – even worse that I started seeing another cashier. Oops.
Around this time, in high school we would ditch the whole day and go drinking – wherever we could. A very close friend was screwing a girl that was NOT his ‘steady’ girlfriend in a camper and I remember walking in while they were going at it. A few months later, she found out she was pregnant and this guy – a guy that had dreams of being a brain surgeon – his life was turned around. Sex at that point became something we became scared of. Condoms became a reality for all of us – what a stupid way to learn.
SP1 Recap: Ended relationship because I had issues with the age difference and had become enlightened to try others.
