This is a true account of my first time.
It's probably fair to say that I was a bit of a late developer. During my teens I was very shy and found it very difficult to ask girls out. My first kiss was when I was grabbed by a girl at a school disco during the last 'slow' dance. Even this was not enough for me to go for it despite really fancying this girl. As an older man I look back and can now see lots of interest from girls and opportunities that I either failed to see or take.
I left school and got a fairly boring job in a smallish office of around 20 people almost all of which were women. In this environment I was very much a boy and still very much a virgin.
After being there a couple of years I got a new, female manager called Kate that I got on really well with. We both shared a similar sense of humour and would banter quite a bit. At the time she was 28 and I was 20. She was also in a really serious relationship and due to marry her fiance the next year so I felt that yet again I was going to miss out.
Luckily for me though Kate's fiance turned out to be a bit of a dick and jilted her a month before the wedding (after it had all been paid for) and left her for another woman. I then turned from the 'funny chap from work' into a nice, and I hate to admit it now, 'safe' guy to hang out with.
We started to see each other out of work, going for drinks or the cinema but through all this despite wanting to make a move, I just couldn't believe I was in with a chance. Eventually I was invited round for dinner.
We had a lovely meal, chatted a bit and for the first time even had a bit of a flirt. Kate asked me why a decent looking guy like me didn't have a girlfriend to which I replied that I'd just not found the right girl yet. She then asked if I liked her, which I'm sure made me go very red, but to which I had to say yes, I thought she was great.
Kate then said that after everything with her boyfriend that she couldn't get into another relationship so soon and that though she liked me, it was just not going to happen. Obviously I was pretty crestfallen. Then she said: 'We can't go out but before you go, would you mind giving me a kiss'.
Kate was about 5'6" with short dark hair, a good figure, smallish breasts and that night she was wearing some smart trousers and a thick jumper. She had taken her bra off before I arrived and through dinner I'd been able to make out her breasts wobbling slightly through the material.
I came over and sat next to her on the two-seat couch and went in for our first kiss. She had great lips and we had a wonderful, slow and sensual kiss. It seemed to go on forever and neither of us seemed to want to stop so I carried on. I ran my hand through her hair, gripping it firmly and giving a gentle tug which made her moan slightly. I then decided to be a little bolder and moved my hand up the back of her jumper, stroking and gripping. I had a huge hard on by now which was getting uncomfortable in my jeans.
Bolder still I moved my hand down and eased it into the waistband of her trousers, cupping her buttocks. All this time we continued kissing, exploring each others mouths with our tongues. She then broke off at this point telling me that if we were going to do this I should understand that it was a one off. I agreed though I would have agreed to anything by then.
We then moved to the living room floor, stroking each other, kissing and started to remove our clothes. First my shirt and then shoes and socks and then, for the first time, she touched my cock through my trousers, rubbing it slightly and looking very turned on. She undid the button and very slowly unzipped me before reaching her hand inside and exposing my cock. This was unbelievable to me and I was feeling great. She then lowered her head and begun to lick along my shaft before enveloping the whole thing. Her head bobbed up and down and it felt wonderful.
Kate was still fully dressed at this point and I was desperate to see more of her so I pulled her off me and began by pulling up her jumper, kissing her tummy slowly as I did so and then as she pulled it over her head I finally got to see her small but perky breasts. I kissed them and sucked the nipples before working my way down her tummy again and unbuttoning her trousers. I got these down and found a very damp pair of knickers. She urged me to pull them to one side and lick her. I'm not sure that she expected much from a novice like myself but the noises she made seemed to indicate that I was doing something right.
I licked for some time with her writhing beneath me before I judged that it was time to get down to the action. We broke off while Kate got a condom from the bathroom and then she very sexily put it on my cock with her mouth. She then got on all fours and I positioned myself behind her. This was the moment, I was no longer going to be a virgin. I pushed my cock in and started thrusting. Despite being so turned on I managed to last ages, varying my rhythm, sometimes going fast and then slowing down. Eventually I came inside her with a gasp and we flopped down together on the floor.
We were caressing each other and I thought that would be it but she reminded me that she'd not come yet and I had work to do. She guided my hand over to her vagina and rested my fingers on her clitoris. I started rubbing with my fingers and, with the occasional bit of guidance from her, she started moaning and then writhing till eventually she came.
Despite what she said about a one-off, we carried on for over 6 months. She was a great teacher.
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