My First Boyfriend’s Bucket List of Sexual Activities

My First Boyfriend’s Bucket List of Sexual Activities

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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.

Aryan types

jim bucket list
Jim looked a little like this young man

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.

Nipple Orgasm

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.

Bucket list

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.

bucket list
Bucket list & Missed Connections

This post has been updated but was originally published in 2017

28 thoughts on “My First Boyfriend’s Bucket List of Sexual Activities

  1. A perfect example of why we date. We live a little, learn a little, and then move on to find someone with whom we have a greater connection. Then we live and learn more…

  2. I find it so funny that he made a sexual bucket list
    What an active sex life you guys had! Sounds like a lot of fun.
    I have a question… why your brother’s bed? lol

    Also I had to laugh at “if that goes in it will never come out!”
    Sounds like a wise choice not to hahaha

  3. Hi May – I hadn’t read this, but your link in today’s post took me here. Interesting stuff and I can see how some of it formed you. I have “a trip up to Soho to buy a vibrator” in common with you! Great work.

    1. Ah the Soho trip – I was a little embarrassed as I was very young 17 – when we bought it – thanks for reading Posy x

  4. Great personal share! I too used to be attracted to the blonde/blue eyes boys but not so much anymore.
    I have a few past lovers like him, after a while it’s just going through the motions. Wonderful learning experience though. 🙂

  5. “if that goes in it will never come out!” That made me laugh.
    Wonderful post. Its fantastic that you had good ‘firsts’ with him and can look back fondly.

  6. Haha, if that goes in there it will never come out. Love that thought. Thanks for sharing

  7. Though he may not have done it for you in a visceral way, it sounds like you had a very thorough, positive sexual education right from the start, which is not always (usually?) the case, unfortunately. And good on you for saying “no” to the thing you wouldn’t do!

    1. Yes, it was very positive because of the nature of its openness – we would discuss sex – we were very young so I now think “good on us” for having such open communication. For a few years after I did think maybe he had coerced me a little, but as time has gone on and I have had other relationships I realise he was actually a great guy.

  8. It’s wonderful that you got to experience so many fun and new things with a partner whom you trusted with your safety and emotional well-being!

  9. It’s strange but interesting looking back on those old lovers isn’t it. When writing about Ryan, I found that the more I got into writing the more I remembered – stuff I hadn’t thought about for a long while… I suspect it may have been like that for you?

    1. I think you probably really loved Ryan – I thought Jim was great but not sure it was love. -so you may be having good memories because of that x

      1. I believed then and still believe that he was my soul mate. I also believe that he; the man who I was married to at the time I met Ryan, the woman who Ryan eventually left me for and myself had all known each other in previous life. Funnily that pic of me with dirty feet was triggering, because I had dirty feet in the cell they threw me into before I was burned and that really bothered me. Ryan lit the flames, when I first met him this time around I wanted nothing to with him because he like to play with fires. My ex was a higher ranking man who did nothing to save me and the woman who was jealous of my relationship with my lover turned the villagers against me even though I had been their herbalist/healer. They wouldn’t have got me, but I wouldn’t leave me animals… And you are the first person I’ve told this to outside my original circle of friends… Phew…

        1. Wow, Indie – that is so interesting. I am honoured and I believe you. I certainly feel I knew my man in a previous life. When I met him for the first time, just over twenty years ago, I recognised him – even though I had never seen him before. I should say my soul recognised him. We parted, but my heart knew he was the one and our time would come…

  10. I really love this. It seems so positive, the way you have started with sex and how adventurous he was, even though you later understood that you didn’t fancy him. I wish I had some of these experiences in my younger years.

    Rebel xox

    1. Thanks, Rebel, it took me a while to realise how fortunate I was with some of my early sexual experiences. He really was very open and intelligent. He married someone from the Netherlands in the end 😉 x

  11. Such a great story, despite the kinda sad ending. It would have been great if there had been more sexual passion for you in the relationship, but you can’t argue with how things are (reality!) so good on you for recognizing it and moving on. At least you got a few orgasms along the way, which is more than some people get (sadly).

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