My name is "Sally." I'm going to write about the two times I lost my virginity. Yes, two. I count them as two separate firsts, because one was making love and the other was fucking, and you have to experience each if you want to really know what sex is like.
The summer after my senior year in high school (after I had turned 18), I was dating a shy boy. He was very sweet, though, and I felt like I was in love with him (although looking back it was just puppy love). July 4th weekend rolled around, and all we'd done so far is kiss. But this night we were parked in a car and we made out for a long time. I kind of thought he might try something cause even though we were sitting up I was pushing against him and stuff, but he was so gentlemanly to try anything. I was frustrated but it was kind of cute too. So I finally asked him did he want to take it out. And he actually said, "What?"
And I said, "Uh your dick." He kind of looked at me for a second but I said, "It's ok" to reassure him.
So he started to unzip and he was gonna just take it out of the hole in his briefs. But I said, "No pull your pants down." He was breathing really fast now and I was so fucking wet and horny! The moon was out so there was enough light that I could kind of see. At first I just looked at it and I think we were both turned on a lot just by him having his dick out and me looking at it. I started touching it and just squeezed it a little. I'd read about how you were supposed to stroke it, but when I tried to move my hand up and down it there was too much friction. I think I giggled a little even. I knew what I was gonna do though. I bent over and took it in my mouth and just held it there and sucked it -- like literally sucked it. He didn't last long cause he'd never done anything before, so he shot all this come in my mouth. I liked swallowing come right from the start but I couldn't keep it all in my mouth this time because there was so much. When I sat up I was so proud of myself that I actually bounced up and down on the seat and stamped my feet a little. But it felt kind of weird too so I helped him wipe up and then said we should go home. On the way home he thanked me several times which made me smile from ear to ear! After he dropped me off, I went to my room and just thought about what we had done for a while. Then I realized I was really horny. I guess I was just so amazed that we did it that I had forgotten how wet I was. I got out my vibrator and I fucked my pussy with it while I rubbed my little clit. I swear I fucked myself all night. I just couldn't stop. I'd do it and come and start to fall asleep, then think of how his cock looked or how it felt or how it tasted or just the look on his face afterward and I'd need to fuck myself again!
I knew it wouldn't be long before we finally did it, so I went on the pill. When the shy guy's parents were out of town, one of my friends covered for me and said I'd be staying at her place overnight. It was fun being at the guy's house without his parents there, but also weird because it felt like we were living together or something. I made dinner for us and washed up while he watched TV. Yes, I know it's totally pre-feminist but what can I say I was just so giddy with playing "wife" that I loved it.
Then after dinner we watched TV on the couch, but it wasn't long before I was licking his ear and kissing his neck. It was hot cause he was really getting turned on and I knew what we were going to be doing soon. But Jesus was this guy un-aggressive! (I'll bet you anything he's on his hands and knees somewhere right now kissing some woman's high heels. At that age I didn't know enough to try Domming him or even realize that I like it sometimes.) After what seemed like forever I finally said, "So you wanna go to bed?"
We got to his room and I started pulling my clothes off. He watched for a moment (it was kind of sexy being watched undressing), but then he took his clothes off too and we got under the sheets together. We were feeling each other up but he was too tentative with my pussy so I took his hand and showed him how to get his fingers between the lips and into the hole. I'd figured out how to stroke a cock by now so I was doing that and I was really tempted to just jerk him off: I wanted come on me NOW! But I wanted fucked too so I slowed down. Finally he took the initiative and got on top. He starts poking around but he's not really getting close so I reach down and guide him in. He didn't last long of course but I was like, "Fuck yeah! I've got come in me!" He asked did I like it and sounded kind of worried that I didn't. But I honestly did like it a lot even though it didn't last very long. I gave him a big smile and said "Yes, I loved it! Can we do it again in a few minutes?" The second time he lasted a little longer, and he tried to go to sleep after that. But I kept playing with his dick and rubbing my pussy against his leg and stuff till he fucked me a third time. That lasted long enough that I finally came. I discovered that night that I'm a screamer!
He was a sweet guy and it was a beautiful first time, but I still count another time as my second first time. It's like my first first time was my sweet losing my virginity and my second first time was my getting fucked losing my virginity.
My parents took me on this cruise and of course I buy this insanely small bikini. My dad was like, "You're not wearing that!" I thought I was going to have to fight about it but I was surprised to find that my mom took my side and said that's what girls wear now. During the cruise this middle-aged guy started flirting with me. This guy was really pretty smooth, cause he got to know my parents as soon as he started flirting with me so they'd be comfortable with him being around a lot and wouldn't be suspicious if they saw me with him. He was a lawyer and I pretended I was really interested in becoming an attorney, at first cause I was flirting with him and then because it made my parents happy to see me talking with him all the time cause they thought I was getting interested in a career!
So one day we're on deck sitting on deck chairs in the sun and flirting like crazy and we notice this woman looking at us really disapprovingly. She's too far away to hear but he smiles and says, "I think that woman thinks I'm a bad influence on you."
I said, "Maybe she thinks I'm a bad influence on YOU!"
He laughed and said, "Maybe you are."
So my heart was racing and my stomach was doing flip flops but I said, "Maybe we should go back to your cabin so she can't see us." He smiled and nodded and all I could think was, "Ohgodohgodohgodohgodohgod!"
When we got back to the cabin I wasn't sure exactly how far we'd go or what he'd do, but when the door closed he kind of leaned over me so I had my back against the door and he was towering over me. (So hot!) He started asking me questions: "Do you have a boyfriend?"
"Kind of, but he's really young and immature and he's back home." (Yeah, it was low to say that about the nice guy behind his back to another guy. I do feel bad about that. But I was young and horny.)
"Have you slept with your boyfriend?" (It made me so wet that this older guy was right next to me asking this intimate question!)
"Yes."
"Was it good?"
"Kind of, but he wasn't very experienced and I'd like a more experienced man."
So then he just starts looking me up and down. He's staring at my tits and my legs and how my bikini bottom is so tight against my pussy that you can see the outline of the lips. I was breathing heavy and my nipples were hard. I couldn't stand it so I said, "What are you going to do?"
And he takes his hand and gently puts it under my chin and lifts my face up to kiss me softly on the lips. It was JUST like in every TV movie you've ever seen! He was really great. He knew just what to do. We kissed for a few minutes really romantically with my back to the door, then he stepped back and took my hand and led me over to the bed. He sat down and told me to take my bikini off. I was kind of scared but it was also really hot to strip for him and I didn't want to disappoint him so I did it, as gracefully as I could (given how I was wedged into those bikini bottoms!). Then he undressed. Honestly, I was kind of shocked how different his body was from the first guy. I mean I should have known. This was a middle aged guy as opposed to a teenager. My boyfriend only had a little hair on his chest and he was so skinny. This guy was SO HAIRY and his body was more filled out the way older guys are. (Think of Dustin Hoffman in The Graduate as opposed to in Kramer vs Kramer. You'd do either guy but they're just really different.) I guess he could tell I was unsure cause he sat me down on the bed beside him and took my hands and put them on his chest. I ran my fingers across his chest and got used to the feel of his body. Then I held him and pushed my face into that hairy chest. He put his big arms around me and my boobs were squished against his big hairy chest and he hugged me and I felt so small and sexy. All of a sudden I was back to being super horny. I didn't especially have a thing for older guys before this but that experience made me a total convert.
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