This is a story of one of those 'first-time' experiences that all guys have dreamed about having and, I should imagine, the kind a lot of girls fantasize about giving. It happened to me when I was a lot younger than I am now and sex was an entirely different game...
At the time I was still a lustful and vastly inexperienced teenager living with my parents and half studying at school. I was good at school, did well at my studies but never had a proper relationship with a girl, it's not that I was unpopular as I had many friends, male and female. My main problem was that whenever I was in the company of a great looking girl, for some reason (and apparently few guys feel the same) I had an uncontrollable urge to be nice to them. To be friendly, warm and understanding. What puzzled me is that girls at this age loved me, they could talk to me about anything, including sex, but not one ever fancied me. I had the hated title of 'friend', it is painfully obvious that at my age girls want a guy with too many designer labels and too much confidence for his own good. I thought I would never reduce myself to that so I began to think I would be a virgin forever.
On the way home from school on a tiresome Monday afternoon Becky, a sexy brunette friend of mine with a great figure and glasses that made her seem even sexier, caught up with me
"I'm glad I didn't miss you" She said, a little out of breath from running after me, "How was Chemistry? Did I manage to avoid any homework?".
She had missed chemistry, the last lesson of the day, to be with her ape of a boyfriend. His name was David something and he was 17 and played for the college football team (Soccer as you Yanks would call it) . He wore expensive clothes. I hated him.
"Yeah, but you'd better catch it up, Bruford's having another which-hunt on irresponsibility."
I'll spare you the rest of the dull conversation and get to the relevant bits, I asked her how things were with 'Dave'.
"He asked me to show him my tits the other day" she admitted quietly, I can understand his needs if not his methods, Becky has a great chest that she always does well to highlight with her tight tops and low cut shirts.
"I thought it was sexy at the time but he wouldn't let me get dressed again, we just sat in his car as he kissed and touched my breasts". You can understand I found this concept very appealing and I was getting a little uncomfortable as the image of a topless Becky caused a strain on my tight jeans. I tried to tell her (again) that this David guy was bad news, she seemed almost to agree but was scared of what he might to her if she broke up with her. I must say that I was concerned as well, she and I had been friends for years and I didn't want to see some numbskull hurt her because she wouldn't suck his dick.
We ended the conversation as we parted for different roads and I went home to think things over. When I arrived my Dad came down and told me that they would be going out around 7 tonight an Sandi (san-dee), the usual babysitter would be here to look after my younger sisters. I was never disappointed to hear she was coming over, I had a huge crush on her. Sandi was 18, she was at the local college taking Fine Art, she was a tall blonde with long legs and fantastic breasts. There were many occasions I laid in bed at night as she watched TV downstairs, imagining her posing nude for my very own artistic pleasure.
At around 6:45 as my parents started to leave, I got a call from Becky. She was calling to find out the homework she missed but she seemed a little rattled and I knew there was another reason she called. 'Dave' made his second appearance of the day in our conversation. She had gone out for a coffee with him and one of his teammates.
"Me and Dave, we were sitting there, getting close when this other guy, Sam, starts asking questions. "Broken her in yet have you mate?" he says. Dave said we had done it loads of times. He started telling him all sorts of details about our sex life. I've never slept with him Alex (that's me), honest"
"It's OK Becky I believe you, what kind of things was he saying?".
At this point the doorbell rang and Sandi arrived, she smiled at me and poked me in the ribs playfully as she passed, I admired her again despite my 2 inch height disadvantage. It was summer and the evenings were warm enough to excuse shorts and girls rarely need an excuse to wear revealing clothing. Sandy was wearing a pair of tight denim shorts that hugged her extremely closely they were cut off well above the knees. Her top was bright red and stopped above her unpierced belly-button. It held her round, firm breasts tight enough to let them move as she ran but not as she walked. The outline to her patterned bra was clear through the material. Her blonde hair was tied back and fell just short of her waistband, her fringe falling over her smooth face that contained her big brown eyes and delicate lips. One of the great things I like about her was that she war hardly and makeup and this highlighted her natural beauty.
"Loads of stuff" I snapped back to reality,
"He said we fucked in his car, that every time he scored on the field he scored in my bedroom. He said I gave him blowjobs while he was on the phone to his friends. Dave even boasted that while we were at that trophy evening where he got his 'golden goal' award I had my hands down his trousers during the other presentations, that I stroked him off for half an hour before we went out and he came on my tits."
As I sat there my dick got harder and harder, I felt guilty but I had gorgeous brunette cheerleader on the phone describing erotic situations to me and an 18 year old Arts student in the next room. I eventually persuaded Becky to get rid of David before she ended up regretting something and the call ended there. I was now extremely horny and wanted to get some relief before going to see Sandi. I booted my Laptop PC and pushed my magazine stack against my bedroom door. I loaded up some of my favorite pictures of Britney Spears and unzipped my jeans, as I had done for many lonely nights I reached for the tissue box and stroked myself off as I lusted for Britney's stunning teenage curves. I tried to imagine what she looked like naked as she lay there in her cheerleader outfit and within seconds I was starting to cum. I pumped my hot load into the tissue and then lay back on my bed wishing Becky was here right now. Why did she go for Dave and not me? Why was I not the one feeling her tits?