My First Time

Since I already wrote about my first sexual memory I figured it was time to write about the first time I had sex.

The young man I lost my virginity to wasn't a boyfriend, infact I hardly knew him... I was 17 and spent most of my summer helping my aunt set up yard sales. This is what she did for a living, from May until October she had yard sales. I didn't have to interact with customers, I just helped set up tables and made sure things were in order, I also took signs around town for her to.

My aunt's name was Emily and she lived almost 2 hours from my parents, so I pretty much was living with her for most of the summer. I had a lot of fun at my aunts house. She treated me as if I was her own daughter, she never had any kids though. The week before I was going back home a young man not much older then me started coming everyday to the yard sale. At first he didn't buy anything, but finally he came and made casual conversation with me, though I was sitting in a chair watching everything going on. He was so handsome and sweet, he seemed more mature then the boys back home. I just wanted to kiss him so badly. I was getting sexual frustrated because I had found myself thinking of him so much and I could only masturbate when my aunt was either sleeping or not home.

Finally on our last yard sale he had asked if I wanted to go to a movie and I said yes. I lied to my aunt and told her that I was going with some friends to the mall. Sadly she believed that I had a friend in that town, I didn't. The young man's name was Richard. He was a gentlemen. I had walked to the top of the hill far enough away that my aunt couldn't see me, he picked me up in an old car, I really think it was from the 1970s. I never did ask him what type of car it was but it was nice. We drove around and talked about our life and families and at the movie for the first 40 minutes we just watched the movie.

I can tell you that the theater was dead almost. We were the only ones in the back row, and the next couple was at least 5 rows away, closer to the front. And the other side at the front row was an elderly man. We shared a small popcorn and each had our own drink after the food was gone he started to hold my hand. I had butterflies racing in my stomach, no one had ever held my hand before. The movie started to get boring and I think he could see that I was getting restless, so he leaned in and kissed me. It was as if it was so met to be. I got so caught up in the moment that I started stroking his hair and face. During the kiss he let us hand gracefully slide from my face to my breast then my stomach. I was getting turned on by the kissing but then he pulled away and went back to the movie.

I had this feeling in my gut that I was a bad kisser and wanted to ask but was to scared to. After the movie he asked me if I wanted to go to his place. I said yes and soon enough we were driving to his home. There were no lights on which told me there probably wasn't anyone home.

He gave me a quick tour then we went straight to his room. Once in his room he showed me some writings he had been working on. We talked for a long time then ended up on his bed. The talking slowed down and then he leaned in and kissed me again. This time it was slow and something to savor. A moan escaped my lips. I think we made out for a good 10 minutes, then he slowly motioned my body to lay down. We layed down kissing and with his hands he explored my breast. I could of stopped him but I didn't, I was hoping he was going to masturbate me, I was just so horny. He sat up and started unbuttoning my blouse. The temptation was killing me, as soon as the blouse came off I unhooked my bra and threw it on the floor. He started kissing my neck and made his way to my breast. He tenderly kissed and licked each nipple with care. At this point I was bucking forward a bit. He reached his hands to my skirt and pulled it down along with my panties. I was sitting butt naked infront of him and just had this huge smile across my face.

I didn't expect to have sex that night but I wanted him to at least masturbate me, I really needed it. To my surprise he told me to lay down and spread my legs. He took his shirt off and pants and bought his head my pussy. He came down slowly and kissed my thighs then I felt his tongue on my clit. I couldn't believe the sensations. I began to relax greatly and let him do what he wanted. I could feel my juices running down onto my asshole, that is how wet I was. I had never been so turned on before. Each time his tongue circled my clit I was getting closer and closer then it took me by surprise I was cumming. I had never cummed so hard before, my body was shaking. I didn't moan or make a noise just loud and heavy breathing. I could hear him say "Oh yeah, just like that" as he licked my pussy juices clean. He bought his face up from my love spot and kissed me. We just layed there for a bit and I asked him if he liked it. He said he had loved it. I was feeling really good. An hour had past of us laying there talking then he leaned in to kiss me again. This time he used his fingers to rub my clit. My pussy sprung to live with the touches begging him for more. This time was different though he just kissed the top of my body while rubbing my clit then he pulled his boxers off. His cock looked big, it was the first one I had seen in person though.

He asked me if I wanted to have sex. I thought then said yes. He walked over to his desk and put on a Durex condom. I was laying on the bed nervous, I had heard bad stories about the first time sex. I spread my legs and waited for the pain to start. He slowly, very slowly just let his cock explore the outside of my pussy. Every so often he touched my clit, it felt so good. Suddenly the feeling had stopped and I felt a harsh sting course up my body. He was trying to get his cock inside but I kept resisting. "It hurts...Go slow.." I had tears in my eyes. He calmed me with a kiss and said it would hurt. What ruined it for me was when I felt him inside a bit further I could feel a coldness dripping down to my ass. Each thrust as a painful sting. He kept kissing me. Whenever he kissed me it didn't feel quite as bad but I was in a lot of pain. He was going very slow and yet it still hurt. After 20 minutes of this, I had a bit of numbness down there and I couldn't feel as much. I asked him to go a bit faster. Once he had a rhythm going I could tell he was enjoying "Oh... Your so fucking tight baby." I started feeling light stings but some pleasure too. I told him it felt good and to keep going. the feeling of him enjoying it was turning me on.

Before I knew it though his thrust slowed down and he pushed his penis far inside 4 times which hurt then he pulled out. He kissed me and asked me to get up. When we both got off the bed there was a huge spot of blood on his covers. I was so embarrassed but he told me not to worry.

He was nice and let me clean up in the bathroom. I didn't like the after soreness I had from sex but I ignored it. He drove me to the top of the hill before my aunts street and asked me to hangout the next day.

That night when I was in bed I felt a bit of depression for not saving myself for an actual boyfriend but I really liked this guy. I had dated some guys at my high school but never could see long term with them. This guy was different though.

The next day I lied to my aunt again and she believed me. This time He didn't have his car instead we walked around some parks talking. He took me to a quiet area by a deserted beach. He had bought a blanket with him. We spent the night talking but then the same thing started to happen we kissed and touched. This time he asked me if I wanted to suck him off and I said no because this was my last night here. I lied to him because I didn't want his cum in my mouth. I was selfish and didn't care. We ended up having sex again but the fear of being caught ruined it for me. He was having a blast though. I was close to cumming but he pulled out and sprayed his cum on my breast. I got angry and asked him for a towel. He offered me the blanket. It was at that point that I realized he had no condom on, which angered me. He told me not to worry because he had pulled out. I quickly got my clothes on and ran away crying.

At first it was innocent but I liked this guy and felt used. He never came around before I left to get the bus back to my hometown.

Oddly enough the next summer when I was 18 the same thing happened, he showed up asking me to hang out. He later told me he had a girlfriend of 3 years. My heart sank, I was the other girl... I didn't feel bad though because that summer I had a boyfriend. Like the summer before we had sex again but more often. While we were apart I had sex with my boyfriend and learned some things. Richard was surprised at how active I was and apparently i gave great head. As the summer ended the last night we had sex I had let him enter my ass. I wouldn't even let my own boyfriend but I let Richard.

To this day the memories of those 2 summers haunt me in a good and bad way. The sex with Richard was amazing but we never got together. And after my final summer there I never saw him again. When I got back my boyfriend knew I cheated. He said he could sense it and dumped me right away. My regret was losing my first love because I had cheated. But I didn't regret giving my virginity to Richard from my 2 summers because it felt right.