Where it happened: home
Langauge: English
Sex: Male
Rating: 7
Category: Straight
OK, Great site. I can’t stand those fake stories that say’s “Yeah I laid my mom’s friend” so Let’s start with some background, cuz if you’re like me you get much more hornier if you know the back story and that this actually happened and not some body’s wild fictitious story . So this happened during the summer of ‘94 when I was 18. I was in college and just started hanging out with a group of new friends. That summer, I went over to one of my friend’s house and I met her family. She had 2 younger sisters. One was 16 and the other was 14. This is going to be kinda weird. So here we have 3 sisters. 18, 16, and 14. And NO! This story isn’t going to turn into a threesome…I WISH!. Well all three of them ended up having a crush on me. The oldest, was a 100% tomboy and I wasn’t really interested in her at all. The 16 year old was a total flirt. She was short, about 5’1, but had big soft tits (34C). I always flirted back at her and was kinda attracted to her tits. I usually hang out with the 18 and 16 year old in a big group. Sometimes, the 18 year old is busy so just her sister would come out with us. I loved flirting with her and night after hanging out it was really late and when we dropped her off. Her parents had bolted the door (as punishment) so she couldn’t go home. She ended up sleeping over at my place. We stayed up all night talking and flirting and play fighting. I got a horny cause I could see her soft tits bouncing all over the place. I ended up shoving my face in her tits and fondled them while she laid on my bed for about 30 seconds :p. One of our other guy friends was with us, and he just sat in a chair watching. She was somewhat of a tease, but I think if I had pushed for more I would’ve gotten it. But being a virgin and having that “good boy” reputation I didn’t go any further. Well anyways, as the summer went on. I found out the sister that I was most attracted to was the 14 year old. Actually I thought I was in “love” with her at the time. She was definitely the cutest of the three sisters, but also the shyest. I didn’t find out she had a crush on me till much later. But when I did, we ended up talking on the phone and started to secretly date… I only told the two guys in the group that I was closest to. It was pretty rough, I would come over and sit in the living room, I could talk to everyone there,yet I couldn’t talk to her less someone find out about our secret! She would always try to find some reason to sit next to me or talk to me, and a couple of times her 2nd sister would be giving her these dirty looks.
Anyways fast forward JUMP TO THE GOOD PARTS….We never really got a chance to spend time together alone, since no one knew we were dating..all we could do was talk on the phone, and on the occasion where I come over sit next to her on the couch!. Well you know after about 2 months of “talk” I wanted to touch her bad! Things never really worked out for us. Either I had to work or she couldn’t leave the house. One day we finally got our chance!We were on the phone and arranged a meeting. She made an excuse to her mom, telling her she was going to hang with her friends after she went to school in the morning orientation. But I instead I would meet up with her and take her back to my house. On the phone, I was telling her that I felt really guilty (which I did because of the age difference) but I really loved her at the time. I told her being a man with needs and because I found her so darn cute and hot, I was afraid of what might happen if we were to be alone together. So we laid out some rules. I told her I don’t want to take her virginity because she was too young. She agreed and was like “OK. So we’ll make out. But let’s keep the pants on and the hands above the waist.” I said: “Hands above the waist? So does that mean I can fondle your tits?” She was like “Yes”. Bam….I got a boner right when she said that. We ended up talking about sex that whole night…and I got so worked up, I had to settle myself down (if you know what I mean) I knew she had a boyfriend for very brief while last summer and asked her if she’s ever got fondled before. She said no. The furthest she got with her last boyfriend was a quick kiss. Apparently, she stopped liking him as quickly as she started to like him.
The next day we implemented the plan as scheduled. I picked her up at the intersection we had agreed upon, and took her over to my house. No one was home so we had a lot of privacy. She was wearing matching green basketball jersey with a tank underneath and shorts. I wanted to go slow, so I threw in a movie and went to sit next to her on the couch. But as soon as I sat down, she jumped on my lap and started kissing me! I was shocked! She noticed that I was pulling back so she stopped and asked me if I was OK. I said “Kind of. It just feels kinda weird”. She said. “What? Because of my age?” and I nodded. She started to tear up and said how much she loved me. And I told her I loved her too. But me being 18 and her only 14, it would look really BAD, and people would be upset! But she kept telling me that age didn’t matter and after a while I started to believe that that too. So I told her “You’re right! You’re awesome and age won’t really matter. When I’m 34 you’ll be 30….Big fucking deal!” She smiled and kissed me again. This time I returned the kiss.
After a few moments of kissing and tonguing. I slowly moved my hands down, and began to fondle her tits. They were much smaller than her sisters. She was 32A. I fondled them outside her jersey for a few minutes, then I stopped and looked at her. She returned my gaze and smiled. Then she pulled off her jersey and tank so that I could see her bra. She was wearing a black bra with laces on the edges. I smiled…(I had told her the night before that I thought women in black bras turned me on). I unhooked her bra and took it off. I was thinking, Wow, this is really happening. (In the past I’ve made out and fondled a lot of tits before, but always with the shirt and bra on so this was my first time actually seeing tits with nipples and everything in real life. She had a little mole close to her nipples. I forgot which side) With that, I opened my mouth and started sucking on her nipples. This went on for quite some time. I was obsessed with her tits so sucked and licked her nipples, switching back and forth between her right and left tits until they both started turning red. I asked her how it felt, since this was the first time her tits have been fondle or sucked by anyone and she said it felt good. Well as you can imagine, I started getting really horny! The next thing you know, we were on the floor. And I was dry humping her! She knew I was horny cuz she could fell my hard dick rubbing against her thigh. I couldn’t control myself, and I grabbed her hand and slowly glided it down to my dick. I still had my pants on and she just rubbed her hands on top of it. In between the kissing and sucking of her tits, I asked her if she knew what to do with her hand. She said no. She’s never even seen a porn before! So I unbuttoned my pants, took her hands and wrapped it around my dick and started moving it up and down. She was like, “does this feel good?” and I told her yes! After a while, I was getting soooo freaking horny, she was still moving it up and down and playing with my balls but not fast enough to make me cum! As she was doing this, she mentioned the rules we laid down on the phone the night before and I told her: “No, We’re definitely not going to have sex today. That’s why I purposely didn’t buy any condoms.” But we had already broken the “above the waist” rule. So I said OK. NEW RULE!!! Hahaha. Let’s just enjoy ourselves, but NO SEX. She nodded in agreement. So then I said, Well since there’s “above the waist” rule, can I touch your vagina? She smiled and said yea. So I slipped my hands down her shorts and found her vagina. She spread her legs apart and I started to teasing her by moving it around her lips. I asked her how that felt, and she said it felt kinda weird. Next I slowly slid my finger into her vagina and started moving it in and out. She closed her eyes and started moaning. She was like “it feels so weird but also really good at the same time”. We spent several hours lying on the floor. I kept sucking on her tits and fingering her and she was giving me a hand job. As we kept doing this I got so freaking horny that I wanted more, but there was that freaking “no sex rule” and both of us was intent on not breaking it! She knew I was really horny and that I wanted more than the hand job. So she asked me, “What else can I do? You’re so horny right now but we can’t have sex”. So I told her “Suck it!” She was just like what?! I told her. “Give me a blow job”. She was like “That’s gross.” I told her no it’s not. All girls do it. She was like “I thought only porn stars do that”. I told her “That’s not true.” So she said OK. But she didn’t know what to do. She said her friends joke about it a lot but she’s never actually seen or know what it really entails. So I told her to just open her mouth and pick my dick in it. Then, pretend my dick is a lollypop and suck and lick it. She nodded and started doing just that. This was my first EVER blow job and I was in heaven…..Thinking back on it, she actually did a real bad job…but being the first blow job I’ve ever had…it was awesome. She was licking and moving her head up and down and a couple of times she stopped and said…”It taste’s funny”. I didn’t want to tell her it was my pre-cum that she was tasting, since that might gross her out and make her stop :p. Well she continued and it didn’t take long before I shot my load. I pulled it out of her mouth just in time and I squirted on her cheek. Afterwards, as I was lying there. I started feeling guilty again. So I told her how sorry I was. We were only supposed to meet, spend some time together and have a little make out session. But it turned into her sucking my dick till I came. She was like, don’t feel guilty. I wanted to do it….Then she smiled and said why’d you think I wore these shorts. They come off and on real quick, in case someone walks in on us. :p.
We ended up having sex a few weeks later. But the story isn’t as intense as this. It happened in my bedroom that time. I had bought a condom, and slowly pushed it inside her. Every guy talks about how crazy their first time was but for me it was OK. It felt great, but during the whole losing virginity my dick hurt like hell. I’m not circumsized so when I put it in, the foreskin folds back and rips, and that shit hurts like hell! And it keeps hurting each time you go in and out. I’m about 7.5” in length and my girth is about the size of a bratwurst so I don’t know if that’s considered big or not. But it didn’t stop hurting until probably the 20th time I had sex. That’s when my foreskin finally got used to being pulled back so far and sex was much better after that (no pain). We broke up shortly after she went back to school. I was heartbroken, it wasn’t until years later that I came to realize that everything we had was just a dream. The age gap of 34/30 doesn’t matter…but at 18/14..it’s matters quite a bit! We were in two different worlds. I’m 34 now, married with children. But I still remember the great time I had with her.
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