The Story of My First Times - Cover

The Story of My First Times

by D.T. Molton

Copyright© 2025 by D.T. Molton

True Story Sex Story: A short story about a man's first sexual experiences

Caution: This True Story Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   True Story   Anal Sex   Oral Sex   .

Where does one start a story like this? I suppose the firs thing to say is that the names in the story have been changed to protect people. I know people write stories like this all the time and say it’s true, but I have to admit I do wonder sometimes, is it really true or are they making it up. Well in this case you’ll have to take my word that this is true to the best of my recollection given how many years have passed since.

Growing up I was painfully shy, these days I suppose I would be classified as neurodiverse, but back then it was “reserved”, “quiet”, or, as noted, “shy”. I had my groups of friends that I hung around with in school. I went to the all-boys school a.k.a. the academy, one of three in the town, the others being the convent (all-girls) and the “tec” (mixed). Other than a bit of background they have no real bearing on the story. The only thing aspect from those days is to mention the graduation ball held by our school or Debutant ball. I wanted to go, but I didn’t want to stand out by going stag. There was a girl I want to ask, Caroline – a student at the convent, but it took me a long time to get up the courage, but one day one of my classmates forced me to wait for her outside of the school for one of the classes the convent girls attended at the academy and ask her. She agreed to go with me, but as I later discovered it was because she may have been interested in someone else rather than me. It was a great night, but not part of this story, so we shall bid it farewell.

Fast-forward a year and I am at third level at a well-known university attached to a seminary. I was living on campus, still the “reserved” guy I had been to the point that as my accommodation had in the past been for noviciates people wondered if I, too, was on the ecclesiastical path. (Hint: I wasn’t). It did take me some time to settle into university life, which I enjoyed, but meeting people was difficult as there were several hundred in one of my lectures and a lot of work which I was focusing on. During the year some of the guys I lived with got to know a group of girls and we would often visit their apartment. Like my hostel it was part of the campus and consisted of a spacious main kitchen/living area and five bedroom and a bathroom. The bedrooms were a decent size, fitted out with a desk and bookshelf, a single bed and a fitted open wardrobe.

It was there I met Claire Murphy, like me she was very quiet and we felt a certain kinship in that. We met up a few times that first year, but I suppose we were just unsure about things. Claire was close in height to me although a little shorted, she had dark blonde hair and wore glasses with a rather strong prescription. Apart from that she was quite good-looking, although she tended a bit toward being frumpy. Over the summer I wrote to Claire and I think I hinted that I’d like to see her when we returned to college.

The following year, when a new flatmate arrived things changed. Erin was American and took Claire under her wing. She worked diligently to bring us together until eventually, she simply dragged Claire over to my hostel, asked for me and told us both we were going on a “date” the following evening.

“It doesn’t matter what you do or where you go, walk around the old campus, walk the canal, whatever, just spend some time with each other and talk”, she said.

The other guys in my hostel were stunned when they heard and offered all kinds of advice. I can’t remember any of it now, but suffice to say I didn’t follow a word of it.

I presented myself at her apartment the following evening at the appointed time and we headed off, totally unsure of what we were going to do. We opted to take a walk, avoiding areas where people we knew would be and talking for quite a long time. It was late when we got back to her apartment, but we agreed to do it again.

It was the moment standing in the foyer of the apartment as I was turning to leave that it happened. We both seemed to have the same thought at once and kissed spontaneously. I later learned that for her, as it was for me, it was the first time she had kissed someone.

Over the following days we met up for more dates, greeting each other with a kiss and ending with a kiss, sometimes staying in the apartment withdrawing to her room when people got too curious. While some speculated about what we did, it rarely went beyond second base and clothes didn’t come off as you might expect. Erin followed the development of the relationship encouraging Claire.

I can’t remember precisely when we began to remove our tops and kiss in her room, me topless, her in just her bra. We enjoyed doing it and I spent many evenings with Claire. Third base was beckoning both of us. We began to explore further and further, she stopped wearing her bra when we were topless and now we were being more intimate, initially fondling our jeans, then opening our zips, finally slipping hand through the waistband.

Claire would often change into her pyjamas as I left, pulling her bottoms over her panties. Eventually one evening I asked, “Could I perform oral sex on you?”

Claire paused, seeming unsure what to answer.

“It’s okay”, I continued, “You don’t have to say yes, it’s entirely your choice”

She stood there topless, like me, in her jeans, then hugged me whispering, “Yes”

She locked the door quietly, then turning back to me slid off her jeans and panties. For the first time I saw a girl naked completely. I was awestruck seeing the entire view for the first time. Her breasts, which I had seen and fondled were topped with pink areolae and nipple, they were a round full shape probably a C or even D cup. Downstairs her “lady garden” was untouched. It wasn’t busy, hiding her vulva, nor was it sparse, it was well balanced between both. After a moment, I also removed my remaining clothes revealing the erection she had only ever felt and never seen.

Naked together for the first time we hugged and kissed. She lay on the bed and I kissed her, I suckled on her breasts little and then started to perform oral sex for the first time. I took a moment to look at her fanny as Claire parted and drew up her legs. I had no idea what I was doing or how to do it, but I guessed! Given our earlier activity Claire was aroused so I started kissing and then calling on what I had heard, I began licking, finding her clitoris by accident, but guessing by her reaction it was a good thing (Her family were, by her account, conservative; so her sexual knowledge was limited, I think she said she didn’t know how to masturbate at one point). I spent time there perfecting my technique and eventually giving her an orgasm. I loved the taste of her.

 
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