My Relationship with my first boyfriend Jim was a missed connection in the sense that I never felt a deep connection with him. Although he had so many things going for him and looking back I know he would have been a respectful long term partner.
The Story of Jim and me
I did grow to care about Jim deeply but there was that vital spark missing from my point of view.
At sixteen I thought I was attracted by very tall blond haired blue eyed young men. Later I realised what really turns me on is dark haired, dark eyed brainiacs! But back to Jim. He was six foot three, skinny with Aryan good looks. When he chatted me up I thought,
“Goodness, he is such a nice looking lad I must go out with him.”
And so we became the popular courting couple on our social scene.
I was a virgin and from the moment we started dating, Jim wanted to fuck me. Being embroiled in a Catholic upbringing meant it took a little time for him to get me aboard his ship.
On the road to enlisting me, we enjoyed a particular sexual experience that has only happened to me once. We were at a friends house with about 8 others. Everyone was listening to music, drinking cider or playing cards. Jim and I found a cosy spot under a quilt on a sofa bed and began to make out.
I had very tight jeans on and as we were in company we couldn’t undress, so he began to fondle my breasts underneath my blouse. He had done this before and I greatly enjoyed it and this time was no different. In fact, as he tweaked my nipples and gently stroked the aureola I began to feel extremely horny. He was thrusting his captive erection up against me and kissing my neck, but didn’t touch me between the legs at all. He didn’t need to because all of a sudden I was overwhelmed, my eyes rolled back in my head and I had an extremely intense, but very quiet orgasm. So quiet Jim didn’t even realise.
My cherry picked
Jim finally took my cherry when I was 17 and still at school– nothing much to report there really. First time – pretty non-eventful in the pleasure department. More a technicality. But losing it to someone I cared about was important.
It was now that the fun and games really began. Jim already had a proper job. He was an engineer with a large UK company. Although only a little older than me he was very much eager to get on with the business of life. He worked with men. Men who talked about sex, watched porn movies and got drunk. Jim learned a lot. He decided we would try and tackle every possible sexual venture we could – ah but our parents had to go out first …
We naturally started with car sex – and outdoor sex, on the grass, under the light of the moon – for these, we didn’t have to rely on an empty house. He was definitely the driving force and also -fortunately- very open and conversational about sexual activities. He taught me how to give him a good handjob and blowjob. The head he gave me was OK but to me did feel very wet with little technique included. I don’t think I ever really enjoyed cunnilingus until my man first licked me 20 years ago.
Jim was very enterprising and put together a sexual bucket list of things he wanted us to do.
He tied me to my brother’s bed, blindfolded me, and fucked me.
I dressed up in sexy lingerie and he fucked me.
We fucked once, fucked twice fucked three times and I think there was a fourth. One after the other in the space of about three hours. Then we joined our friends at the local nightclub.
We went to Soho in London and he bought me a vibrator and fucked me with it.
He wanked on my face and breasts waited half an hour and then fucked me.
Put his finger or tongue up my arse, then fucked me. Or I put my finger in his arse while he fucked me.
You get the idea.
Wank before going out
He had a very high sex drive – I know this is the case for most 18-year-old guys, but Jim’s did seem quite excessive. For instance, if we were going out for the evening he would usually wank before he met me. Otherwise, he would have a hard-on all evening.
This may have been because he loved me to wear tight skirts and stockings. As soon as he saw that groove under my skirt he couldn’t keep his hands off me.
We had no sooner arrived on holiday, our first together, after a long and tiring journey, when I lay down on my front to rest. Without deliberation, he lifted my skirt, pulled the gusset of my knickers aside and fucked me. The rest of the holiday continued in the same vein.
Funnily enough, there was not a spanking entry on his bucket list. I have often wondered why. Particularly as I like it so much. It may sound strange but this may have been a matter of respect, being from a good Catholic background and still very young. He would have seen it as hitting or hurting, and even though he was persistent about his wants I don’t think that was his kink. At the time I didn’t know it was mine.
No to anal
One thing that was on this bucket list, that I refused, was anal sex. I only had minor cock interaction before Jim, but later in life, as other cocks came and went, I realised that Jim’s member was oversized. At the time he asked for anal sex I may not have had a comparison, but I looked at his dick and thought to myself,
“if that goes in it will never come out!”
Although I was a willing participant in our activities, and looking back very much appreciated his frank and open attitude to sex, I didn’t really fancy him. I would orgasm and mostly enjoyed the experiences but as time went on I wanted to have less sexual contact with him. After three years we split up. I quickly moved on but he was quite cut up for some time. He was a wonderful intelligent, young man and although I thought he was good-looking, I never got that guttural feeling of passion when I looked at him or he touched me. My cunt never throbbed for his hand or cock. That kind of connection was missing.
This post has been updated but was originally published in 2017