I don’t get to tell many people about my first time because what happened was basically illegal.
When I was in high school, we had a family friend, I’ll call him Ben. He was about my Dad’s age, in his late 30s. Tall, meaty kind of guy. My parents are Caucasian, too, like Ben, but I’m Asian, adopted when I was a baby. I had never had a boyfriend or dated anyone, partly because I felt too self conscious about being an adopted child to white parents. So anyway, Ben would come over, hang out with both of my parents. He paid a lot of attention to me. He’d ask how I was doing in school, what kind of music I was listening to, what movies I had watched. And he really listened. I liked that. I had a sort of crush on him. He would horseplay, like grab my hair (lightly) or tickle me on the neck, even in front of my parents. It was flirting, but no one minded. I used to day dream about being his girlfriend and I didn’t know much about sex, but I knew I was feeling sexy for him and I also knew the difference in our ages made things impossible. Once, I was doing dishes after dinner. My parents were watching TV with Ben in the living room. He came in and stood behind me real close, teasing me. I bumped my butt into him as a joke and felt his erection! He held my hips for a and pressed himself into me, but a noise from the living room made him release me and he went back to watch TV.
Another time, we were having a small party at the house. A couple of my Dad’s office mates and their families were over, and Ben was there too. Everyone was drinking wine so the laughter was really loud. I had decided to dress a little sexy, feeling kind of grown up. I had on a halter top kind of dress make out of this really soft, silky and clingy material. I had on bikini panties and that’s it because I couldn’t wear a bra or the straps would show. So anyway, Ben sat across from me at the dinner table and he was really quiet, kind of staring at me, especially down the front of my dress, even though it wasn’t that revealing.
After dinner, we were sitting in the family room. Everyone else was playing board games but Ben was sitting in the LazyBoy. I went and sat on the arm of the chair, pretending to watch everyone else playing. Ben’s arm was behind me and in a little while, he was running a finger gently up and down my back. It gave me goosebumps. I pretended not to notice. I straddled the arm of the chair and that felt good because I could press my pussy against it. The skirt of my dress was short but full so I wasn’t revealing anything. Ben got braver and slipped his hand up the back of my dress and tugged at the panty until he could cup my bare ass with his hand. He had these huge hands and they were hot. I squirmed around on his hand, still pretening nothing was going on, but I had goosebumps from this sexual touching and funny sensations between my legs. I finally lifted my pussy up from the arm of the chair. That must have been what he was waiting for because in a flash, he had his hand there so that when I came down again, the palm of his hand was between my legs, tickling my pussy. I could feel myself getting really wet and it seemed like I was drenching his hand and the chair. We must have been in that position for an hour. Every so often I would shift a little, to give the blood in his hand a chance to circulate, but he wouldn’t take his hand away and when I put my pussy back down, he would squeeze it gently.
Finally, it was time for people to leave. My parents saw people to the door. Ben stayed behind in the family room on the pretext of helping me put the board games away, getting all the pieces back in the boxes. We were both breathing heavily and I couldn’t look up at him as I put the Scrabble tiles away. I could hear the guests and my parents outside at the gate, and I knew it always took a good 20 or 30 minutes for them to say goodbye, so I thought Ben and I would have some time together. Ben was sitting on the floor, watching me, quiet.
As I stood up to put the game back in the cupboard, Ben reached over and touched my legs. It was a slow, sweet move–from ankles up my calves, pressing me gently, caressing my knees, and then stroking my thighs. I just stood there, frozen, feeling his huge hands on my skin, knowing when he got to my panties, they would be drenched. Sure enough, he rubbed his hand on the crotch of my panties and we could both feel how wet they were. I moaned with pleasure because his hand was warm and firm. He lifted my skirt a little and pulled me to him so that he could sniff my panties and kiss my pussy through them. I felt overwhelmed and my knees buckled. I sort of collapsed on the floor next to him, not caring if my parents came back in and caught us like that.
Ben got up. I thought he had changed his mind. Instead, he turned off the overhead lights and locked the door! He came back to me on the floor where I was lying, my heart beating in my mouth.
He took off my dress and played with my breasts for a long time. We whispered to each other. He said he loved me and I believed him. He kissed my nipples and sucked them gently. His hands were so big they covered my breasts. I kissed him, too while he played with my tits. He finally lifted my ass off the floor and pulled my panties down. He got down there at my crotch and sniffed a little and whispered that I smelled really good. Then he licked me slowly and I think he put a bit more saliva in my pussy to make me wetter. He unzipped his pants and pulled them down around his knees. I remember thinking how sexy it was that he wasn’t wearing any underwear. His cock was circumsized and really hard. I don’t know how big it was in inches, but to me back then, it being the first I had ever seen in real life, it looked incredibly huge. He brought it up to my lips and asked me to suck it. I couldn’t quite do that because I didn’t know if he would ejaculate on me so I just kissed it a little (probably looked really prudish, but hey…I ). He was gentle, though, and didn’t insist.
He put a knee between my legs and rubbed it on my pussy, making me spread my thighs further apart. He slowly pushed his cock into me, each time asking if it hurt. It did hurt, but just a little, so I would say I was okay and then he’d push in some more. Finally he was all the way in. I guess my hymen was gone because I didn’t feel anything give, the way I had expected. Must have been from riding bikes or too much gymnastics. Anyway, he starting moving his hips, bucking his cock in and out but slowly, and he’d stop once in a while to check if I was okay. I loved that he was staring at me, and every so often, kissing me on the mouth. It began to hurt a little in my vagina because I was a bit tight. So he stopped and then would start again. He seemed to go on for quite a bit. Maybe he didn’t come right away, because he had to keep stopping to see if I was okay.
Finally, his face contorted (this part scared me a little) and he jerked his cock out of me and collapsed on top of me. He was having his orgasm and his cum was spurting all over my belly.
He asked me if I had come and I said, no, because I hadn’t felt anything different. He asked if I wanted to and I said not tonight. He stroekd the outside of my pussy lips and bent down to kiss me there. Finally, he got me up and we cleaned the mess on the carpet.
Ben suggested that I sneak up to my room and sleep and he would sleep there in the family room (he’d done that before) and get up in the morning to tell my folks he had mistakenly fallen asleep there. I hated leaving him. I wanted to spend the night with him, but he didn’t want me to get in trouble. I did sneak up to my room. My parents were in bed (I found out later that they thought I had gone on up to bed while they were saying good bye to everyone). I didn’t get any sleep that night, reliving what had happened between me and Ben. He must have left early in the morning because when I got up around 8, he was gone and my parents didn’t say anything about him. Mom asked me why I was limping (I was actually walking funny because my pussy felt a little sore) and I said I must have pulled a muscle.
I was so sexually excited for days after that. My panties were always wet and I would fantasize about me and Ben doing things together. I didn’t have very specific fantasies since I didn’t know too much about sex. Ben would come over more often after that, but he was careful not to pay too much attention to me so my parents wouldn’t get suspicious. We didn’t get to have sex again for a while. Sometimes, he would come to me in the kitchen and cop a feel of my ass or breasts, rub his erection into my ass. Very frustrating!
Once he took a day off from work when I had a school holiday, and he came over. We spent the whole day in bed, my bed. He ate me into 3 separate and distinct orgasms before he fucked me and allowed himself to cum. He said he’d felt guilty for a long time because I hadn’t had an orgasm our first time together and he didn’t want me to be traumatized about sex and think it was all for the guy to get off and nothing for the female.
Another time, he picked me up a couple of blocks from school and took me to his apartment and we had sex till about 11 that night. I just couldn’t get enough of it with Ben. I also knew he’d get in big trouble if we got found out.
My most memorable time with Ben was when I got on top of him and rode him. I orgasmed in about 2 minutes. His cock hit my G spot at just the right angle. What made me really hot was looking down at him, seeing his sweet face filled with lust for me and his big hands on my breasts, covering them, squeezing and rolling the nipples.
Ben and I continued to have a relationship until I was in college. By then he was in his 40s and he was going through this thing about being twice my age. I couldn’t believe it but he finally broke up with me and stopped coming around to visit my parents, too. They didn’t know what was going on and would wonder out loud why he stopped visiting them cold.
I’ve been married now for 20 years to a great guy, really sweet and considerate in all aspects. We have a healthy and FREQUENT sex life. I still think about Ben, though, and wish that he hadn’t freaked out about our age difference. He was probably the best guy I know who could initiate me into sex and love.
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Naomi
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