Where it happened: His House
Langauge: English
Sex: Female
Rating: 5
Category: Straight
As I was growing up I always considered myself to be unattractive. I was also shy and had difficulty making friends and meeting new people. When I graduated from high school I got a job at an insurance company and met Kim. We hit it off right away and she asked if I would like to share her apartment with her. I agreed and moved in with her.
Kim was more outgoing and when it came to sex she was experienced. Being frustrated sexually anyway when the conversation turned to sex it only made me want to be with a man all the more. Kim sensed this and took to a doctor to start birth control pills and gave me some suggestions on how to get a guy to fuck me. She suggested someone a little older with some experience to help make it better for me.
I had taken a part time job at a pizza restaurant. The manager’s name was Matt. He was in his late 20’s and recently divorced. I found him to be attractive and found myself fantasizing about him as I masturbated at night. But being shy I wasn’t sure how to get him in my bed or if he was even interested.
One night after close Matt and I sat around and had a few beers. Some how the conversation turned to his ex wife and how he left her when he caught her screwing the guy next door. He became very emotional and as I put my arm around him to comfort him he gave me a hug followed by a deep kiss. Embarrassed by his display of emotion he got up and said we had better leave.
The next time I worked we stayed and had another couple of beers and he started to ask about my life. I gave him all the details about my shyness and my insecurity about life. He told me he found me to be attractive and enjoyed talking with me. He asked me out the next weekend and I gladly accepted.
I was impatient all week for Saturday to arrive. Matt picked me up at my apartment and we went out for a nice dinner and a movie. Leaving the theatre he asked if I would like to go to his house to talk. Of course I said yes.
As we sat on the couch talking about various topics he began to hold my hand. He than asked if he could kiss me. It began as short kisses that turned into long deep French kisses. He began to kiss my neck and upper shoulders. I had never experienced the sensations of being kissed this way and found myself getting quite excited. When his hand wandered to by breasts I knew that tonight I was going to have my cherry popped. His skilled hands found there way to my bra, which he unhooked, grabbing my bare tits.
After a few minutes of the kissing and fondling he asked if I would like to get more comfortable in his bedroom. I could only nod my approval as he took my hand and lead me to his bed. I was so nervous. I still wasn’t sure if I could actually bring myself to have sex with him or whether it would really go that far anyway.
Once in his room we lay on the bed and resumed with the foreplay. I could feel the hardness of his penis through his pants as he pressed against my leg. I removed my shirt and bra allowing his mouth to explore my hard nipples. I realized my cunt was soaking wet as Matt continued to kiss my nipples and neck.
The he asked the question. Would I like to make love with him? I smiled and told him yes, but there was something he needed to know first. At first he looked surprised when I told him I had never done it before. He asked me if I was sure I really wanted to go all the way. At this point I was completely sure that I was ready to have sex and told him so. He then removed his clothes as I removed the rest of mine. We lay together naked in each others arms kissing. I could feel his hard cock pressing against my leg, with drops of precum on its tip.
He then excused himself to get a comdom when I told him I was on the pill and would prefer he not wear one. (Kim had told me it was great to feel the semen ejaculating inside you and that a condom prevented some of the sensation.) He positioned himself between my legs and pressed his cock against my waiting vagina. As he attempted to enter me I could feel the resistence of my cherry. With a gentle push it broke sending a small sharp pain through me. Then Matt began to moan, his cock stiffened and I felf his cum shooting in me.
Embarrassed Matt rolled off me and apologized for not lasting longer. He than told me how he hadn’t had intercouse in over a year since he left his wife and how the excitment of being with his first virgin was more than he could handle. I leaned over, kissed him and told him we could continue when he was ready.
After about 15 minutes I found Matt entering me again, this time pushing his penis in all the way. I had two of the best orgasms ever as he made love to me. We must have fucked for about 15 minutes before he came a second time.
I spent the night with Matt as we made love again before falling asleep. We spent the next morning exploring each other’s bodies as I sucked my first cock and had my pussy sucked for the first time.
Matt and I continued to make love to each other over the next several months. However he was offered a better job in another city and moved. Ironically a month after Matt left I met his younger brother Michael. We fell in love and eventually got married. Michael was a virgin the first time we made love and knows about the affair his brother and I had.
Although I love Michael and we have the best sex together, I still remember that first time with Matt with a great deal of fondness.
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