Loosing my virginity

I have only recently realized that I have a big dick. I realized sometime in school it was above average but never realized how big even with all the clues.
My first time was at a small party. We were at this girl’s house, in the finished basement. Drinking and things that 18 yo kids do. Somehow the topic turns into massages and I say that I think I can give a nice back rub/ massage. One girl, Chrissy, says let’s go to my room and I can be the judge of that. So off we go. She has me turn around and takes her top off and lays face down on the bed and says ok, let’s see what you got. I begin out by rubbing the lotion all over her back and down the sides then begin working areas one by one until I’m down to the sides. I work in them and as I go I begin to graze her side boobs (she has pretty big boobs, prob about a 36D). I realized and made an effort to not do that and finish the sides. I say I’m done unless she wants something else and she says I wondered you were going to massage my boobs. I ask if she wants me to and she said yes, so I begin rubbing them on the sides from behind and work to the front. I tell her I need her to flip so I can do a better job. A little shy but she does, so I begin when next thing I know we are making out while I’m playing with her nipples. We spend the next hour making out and playing with each other topless. I decided I was going to take a chance and see if I can touch her pussy. I slide my hand down into her pants and feel it. It was warm, and wet. She stops kissing, rolls and sits up and unbuttons her pants and kicks them off. Now I’m excited, and nervous cause I have never been this far. I knew she had been with a couple guys and would probably guide me. We go back to kissing and I begin to explore her pussy with my hand and fingers. Having no idea what I’m doing I just awkwardly fumble around with it and insert my middle finger inside. He seems to like it so I keep thrusting my finger. Her pussy is really wet by now. She asks if I wanted to go inside her, and if course I say yeah. She tells me there are condoms in that drawer over there. So I go get one. I take my pants off and walk back to the bed. As I am taking the condom out of the package she starts playing with my dick and says something about it being big and hard. I could have cut diamonds. I get the condom on and it was super tight. The base of the condom hurt but I figured that was ordinary. I get in front of her in missionary and line my dick up and try to put it inside. It’s hard to get in so she says wait and starts playing with herself. I begin to go soft so she played with me and gets me hard again. We try again and I manage to push it in a little. I have a hard time staying hard but manage to get my dick inside her and awkwardly try to thrust a little before going soft. I didn’t know what was happening and get embarrassed. She assured me it was ok. At this point I figure it’s over so I begin to get ready to go back out and she says she thinks I should stay the night in her room. I say ok. We both go back out to the main room to hang out. After not very long people are starting to go to bed so we head back to her room. We made out a little and she stroked my dick for a bit before we went to sleep.
The next morning we wake up and begin to mess around again. It doesn’t take long before we are naked making out. She asks if we should try again I say sure as in rock hard. She grabs a condom and i put it on and we try again. It was difficult and I went soft again. So now I am thinking I have something wrong with me. I take the condom off and she plays with me and get rock hard again. Then she says, try it with out. So I do. It was hard to push inside of her but it goes in. I couldn’t believe how warm, tight, and soft it felt. I try to keep going and she stops me and says it’s enough and to go in and out from there. Didn’t think much of it so I did what she said. After a few minutes I feel like I’m going to cum so I tell her and she says don’t cum in me, I’m not on the pill. So I stop and pull out and jerk off into a solo cup sitting in the night stand.
We kiss and make out for a bit more then get up and dressed for the day.
The next weekend we were back at her house. I was hoping to do it again but didn’t know what to expect. We are sitting around drinking and Chrissy is trying to cheer up her friend Jamie as she just got dumped. Chrissy tells her I give a good massage and she should get one. We head off to Chrissys bedroom and I give her a massage like I did Chrissy. When I get to the sides I rubbed the sides of her boobs and moved to the fronts a little. She turns her head and says, be careful, your turning me on. I half jokingly says, that’s the point. I keep running my hands around and playing with her boobs when I decided to be bold and rub over her nipples. As soon as I begin to slide toward them she lifts giving me easier access to them. As I’m rubbing she lets out a really soft moan. I ask if she needs her legs rubbed and she says sure and lifts her but up to unbutton her jeans and pushes them down to take them off. I help her take them off the rest of the way and begin rubbing her thighs. I move up little by little until I’m at her butt. I keep rubbing and moving my hands around going up more and more on her butt then eventually my hand is under her panties rubbing her whole cheeks. She rolls to her side a little and says I have turned her on but she isn’t sure if she should keep going. I say no worries, we can be done. She puts her clothes back on and just as she finished Chrissy came in the room and asked what we were up to. I had to use the bathroom so I step out real quick and when I come back they are both laying in the bed and tell me to get in. Chrissy says Jamie’s tells me you gave her a great massage. I say hopefully she liked it and Jamie’s says absolutely, it was great. Then Chrissy says, which one would you pick to spend the rest of the night with? I say why not both? She says she is not into girls and Jamie agrees so I say you don’t have to do anything with each other. They agree and Chrissy says I want to see you kiss Jamie. So we begin making out. After a while Chrissy says she wants some, so I turn my head and we begin making out. Jamie unbuttons my pants and starts to pull them down. I stop kissing Chrissy and get my pants off and pull my shirt off. I continue with Chrissy while Jamie starts playing with my dick and says wow Chrissy, you were right. Chrissy responds, see, I told you . Again, wondered nothing of it. Jamie is stroking me while I’m making out with Chrissy and playing with her tits with one hand, Jamie’s tits with the other. Chrissy takes off her shirt so I can lick her nipples. Then she says I want first, I got new condoms for you. I say ok and she goes to grab them from her dresser. Jamie’s asks if I have ever kicked a pussy before to which I say no, but I would. Chrissy comes back to the bed and takes her pants off and lays down while handing me a condom. Jamie was sitting on my left still and proceeds to get nude while I get ready and enter Chrissy. The condoms still pinched me a little but were way better than the other ones so I was able to stay hard. Chrissy stopped me when I was like 3/4 the way in and says that was deep enough. As I was fucking Chrissy I put my hand on Jamie’s pussy and played around. She guided my fingers to her clit and said to rub there. It didn’t take long before I was ready to cum so I said so and Chrissy said she was ready and leaned up so we could kiss. It felt so good to cum inside her pussy. It was amazing. I cleaned up and tossed the condom in the trash can then went back to the bed Jamie said she wanted me to lick her pussy. I said I didn’t know how and she said she would show me. As I licked around she guided me to the right spots. As I was laying there doing that Chrissy grabs my arm and puts it on her pussy so I rub her as in doing this. After a few minutes Jamie starts to pant and breath faster and squirm around. Finally she grabs my head and pushes me in her pussy hard while she cums. I sit up and begin to concentrate on Chrissy using my fingers and I manage to discover her clit and I rub that. Jamie’s tells me to use my thumb and push a little in circles. Before I knew it Chrissy was saying she was going to cum. Jamie she wants to ride me. Something else I had never done. So she has me lay down and she gets on top of me. I get a new condom and put it on. Jamie lines her pussy up over me and slowly lowers herself down. She tells me to sit up and we make out as she rides me. At one point she put her arms around my head and had her tits in my face so I took one in my mouth and kissed and kicked her nipples. After a while Jamie ask if we can do it regularly (missionary). She lays down and I begin to go in and she puts her hands up and says wow, you are really big. Chrissy says, yeah, isn’t he? Jamie says he is way bigger than my ex. Takes directions better too. Chrissy says Aaron (my friend that introduced us) has a big one but not like this. I am not really realizing what they are saying I just focus on what I’m doing and try not to cum. The Chrissy gets on her knees and gets in front of me and starts to kiss me while I’m thrusting inside of Jamie. It was hot. At one point during that Jamie says I want to feel your boobs and put a hand on Chrissy tit, gave it a squeeze then put her arm back down. Chrissy reached around behind me and was pushing my butt while I was pushing in and out of Jamie. I can feel myself building up, I was going to cum soon so I said so. Jamie said she was gonna also. I exploded inside the condom inside her but kept going cause I wanted her to finish. After a few more thursts she says she is cumming. I lay down exhausted and Chrissy rolls on her side and outs her head on me so we can kiss more. I say I need to toss the condom and get up as Jamie heads for the bathroom. I jumped back in bed and Chrissy lays on me in a cuddly fashion and when Jamie came out and comes back to bed and does the same. We end up all sleeping in the bed. The next day I say I have to go drop off something to my uncle and both girls say they want to go with me and we could go to breakfast. Of course my uncle sees that and asks if one of them is my GF. I say neither, I don’t have one. He still brings that up once and a while. If he only knew.
A few weeks later I was at a party out in the woods at a cabin with them. Jamie was with he bf and Chrissy told me she was seeing a new guy. I say ok, and continue in as usual. At one point we had to drive somewhere to drop someone off or something, don’t even remember. Chrissy went with me. On the way back up the 2 track about half way Chrissy said to stop. My car was a hatch back and the seats folded flat. She climbed back there and said come on. We made out for a minute or two then she said she wanted to ride me. She is wearing a jean skirt, shirt showing nice cleavage, and a jacket. She unbuttons my pants just enough to pull my dick out, put a condom on, then slides her panties to the side and lowers herself onto my throbbing dick. She rides me while being bent over kissing me the whole time. After a few minutes she sits up a little and says she is cumming. That is enough to set me over and I cum right after. She collapses on me and we kiss for a little longer before she says we cannot do that anymore, she has a bf. I tell her ok, you were the one that got in me. She says, can you blame me? I cannot help it. We went back to the party and she went rub her boyfriend and hung out at his side all night. That was the last time I ever saw either of those girls.

NSFW: yes

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