First time poster. Been reading this sub reddit for quite a while and I’ve now set up this account to start writing memoirs of my (currently M37) past sexual encounters – of which there are many. These are recollections based as closely as possible to the real events (with a few minor dramatic embellishments), but names are changed for privacy. As such they may be long!
**********
All characters are of legal age.
**********
I had met Amelia a few months before at a club in the next town over from the one in Southern England that I lived in. She lived one town further over again. I had been instantly struck by her as soon as i saw her, within 10 minutes of walking in. She was 5’9, long mousey brown hair, blue green eyes, long legs and a slim waist, but wide hips. She had B cups, but I liked that, generally not preferring giant boobs. For context, I’m 6’2, was also pretty slim at the time with short dark brown hair and brown eyes. She had been with a group of her friends, and I with a group of mine, but we’d ended up spending almost the whole night together, drinking, kissing and running our hands all over each other. But that was as far as it went that night. We had a real connection though, and quickly began seeing each other regularly. I had had a few sexual experiences before, but never gone the whole way, and Amelia had never done more than kiss another guy before me. So in the time in between that night we met and this one, we had begun to explore each other and gradually done more and more. By now we had seen each other naked many times, done oral, fingering, handjobs, all the normal foreplay activities. Tonight however, was going to be special.
It was our three month anniversary, we were in love, and we decided that it would be the night we lost our virginities to each other. Our friends had told each of us what to expect, as we were later to reach this stage than several of them. They said it would be awkward, maybe painful for her, but then get better and start to feel good. They were pretty much spot on as it turned out.
We had been out to dinner and both couldn’t wait to get home. Even though we were technically adults, as students both of us were still living with our parents. We were both permitted to stay overnight in each others rooms, but my parents in particular were pretty cool with letting us have our privacy – and they certainly had an inkling that our relationship was becoming very physical, but trusted us not to do anything stupid. We went to my room and I locked the door, turned on a lamp and turned off the main light. We kissed passionately and began to pull clothes off of each other, until we collapsed onto my double bed together naked. I reached down and began to rub her clit, while she took my cock in her warm hand and turned the semi I was already sporting by that point rock hard.
“Are you still ok to do this?” I asked her.
“I want to do it for you” she replied, “I know you’ve been patient up to now, but I feel ready, I love you.
“I love you too baby” I said as I slipped a couple of fingers inside her already moist hole.
She moaned a little in pleasure, we’d done this part before and I could make her cum like this if I did it right. But that wasn’t the plan tonight.
“Do you have the condom?” she enquired in such a matter of fact way.
“It’s in the drawer of the bedside table”, I pulled away from her reluctantly to grab it, “Do you want to put it on me?
Amelia took the ultra thin condom we had bought earlier that day, and carefully opened the pack, while I laid back in anticipation. She rolled it over my dick, just as everyone was taught to in school sex ed classes years before, ensuring to leave the little gap at the top to try and make sure there was less chance it would break. Once she had rolled it close to the bottom of my shaft, she laid down next to me and we made out some more. I gently rolled her onto her back, cupping her boobs as i did so, and climbed on top of her. We had talked about this earlier and thought missionary would be best for novices like us. I lined up my head with her entrance, and she grabbed it, guiding it in for me. As was to be expected, she was incredibly tight, and it wasn’t easy. My cock is 7 inches in length, but only has medium girth, yet we struggled to get the right angle to make things comfortable for us both. I tried not to force it too hard or fast, but i just wanted to be connected to her in a way that no other action could replicate, so i slowly pulled out a little, then pushed back in, a little deeper, but she put her hand on my pelvic bone to stop me.
“Is it ok?” I said, genuinely concerned
“Yes, it just, hurts a bit, just keep going slow”
I nodded, and repeated those slow shallow thrusts a couple more times until she winced, closing her eyes tight. I stopped again momentarily, my dick about half of its length now inside her, but then she opened her eyes, pulled me closer and kissed me. I took this as my cue to keep going, and after another minute of slowly working my way inside, I was finally balls deep. We kept going for a couple more minutes, now a little more rhythmically. The pain seemed to be subsiding a little for her, but she clearly wasn’t completely comfortable still, and i wasn’t getting as much pleasure as I had thought I would that first time. But then she said something that surprised me.
“Baby, I want to try going on top, do you mind?”
“Ok, sure, if you think it will be better” I replied.
I pulled out and rolled over onto my back. There wasn’t much blood on the condom from her hymen breaking, certainly not as much as my friends had made me believe there could be. Though she was also a keen horse rider, and I later found out that this could actually cause it to have already been partially opened in the past. Amelia got up and straddled me, leaning down for another kiss. As she did this, she reached back and slowly guided my cock into her once more. This time we both seemed more comfortable. She built up to a medium pace, and kept going for a few more minutes, with a few little moans of pleasure escaping along the way. Until she slowed and then stopped completely.
“I’m getting a bit sore” she said, “are you close to cumming?”
I had started to get into it more by now, and was feeling more of the pleasure I’d hoped for, but wasn’t close yet. “No, but it’s ok, we can stop if you want to, do you want me to just finger you again until you cum?”
“That’s ok. Beleive it or not, I HAVE enjoyed myself, even though I haven’t cum, but you’ve seen it’s been hurting a bit too so i think i want to give myself a rest for now”, and with that she lifted herself off of my still hard penis. “As a thank you for being understanding though, I’m going to make sure I finish you off”.
She moved down to the foot end of the bed, her head now level with my dick. Then she peeled the condom off and without looking, threw it somewhere on the floor. She went straight for it, putting the tip of my cock in her mouth at first, but then quickly working most of the rest of it inside her beautiful mouth. Again this was something we had done before, so she knew how I liked it. Two or three minutes later, I blew a full load into her mouth, then she sat up and swallowed all my cum.
Following my orgasm, she slid back up next to me, and we threw the covers over our still naked bodies. I turned out the lamp on the bedside table, and we fell asleep cuddling in to each other, in love, and at the start of what was to be a long and exciting journey exploring everything there was to know about sex with each other.
**********
Hope you enjoyed! There will be more stories to come, many more if this one gets a good reception!
It was sensual