(M)y (F)irst time having sex | 2016

Ok, I would like to hear about the first time you had sex. Was it good or bad ? Would you do it again if you had the chance? So I will go first since I asked the question. I'm using a throwaway account due to the usual reasons. This is a long one, but you can skip down to the bottom for the TL;DR.

The Back Story: I was a late bloomer when it came to dating. With that being said, I was very interested in sex and had reviewed a lot of research (porn) about being a good at it. I was also interested in learning about massage at the time which as I later came to find out was a very good thing.

So after leaving high school I decided I was going to join the military.I was at the recruiting station with a female friend from high school. I wanted to hook up with her, but as she was taller than me, and my game sucked, it was not going to happen.

So anyways we are both joining the military together, and are at our Delayed Entry Program (DEP) meeting. This is when I see a good looking girl walk in through the back door of the station. I'm immediately drawn to her, and I tell my friend that she looks cute. My friend says no she does not, and that I should not talk to her. I said fuck it, and approached the new girl.

So, ask her name and she says "Latoya". One thing leads to another and before long I got her phone number, and her promise to help me study my DEP booklet.

The Main Event:

A few days later I was talking to Latoya on the phone and she tells me that she wanted to come over to review some of the DEP booklet information with me.She comes over, and we review the information for a while and she starts to tell me about how sore her body was. I told her that I could show her some of the things I had learned about massages.

As we were in my living room she lays down on the floor and I start to massage her. I move my hands to her shoulders and start to work my magic. After ten minutes of this, I tell her that the message would feel better if she took off her shirt. She takes off her shirt but leaves her sports bra on and lays back down. We continue this for a while, till she dares me to massage her front of her body.

I take up this challenge turn her over and start to work on her chest. She asks if I was willing to do it without her bra on. I said sure, she takes the bra off and I was able to see her breast were a full D cup. Wanting to give a good massage I took my time working them over. When I had finished the massage, we got up and moved back to the couch.

After some small talk we started to kiss. I employed all the things that I had learned from my first girlfriend, which was while kissing a girl you should try to suck on one of her lips while gently trying to nibble on it at the same time. (this is harder than it sounds)

While I was doing this, my left hand had a firm grip on her hair, and I gently tugged her head back (old girl friend told me about that too ). While my right hand moved down into her shorts. She was cleanly shaven and her pussy lips were wet so i began to tease her pussy. We did this for a while then decided to go to my room.

We both take off our clothes and continued what we started outside. My hands were touching her all over, but my index and middle fingers of my right hand soon settled on being at home in her wet pussy. As I was finger fucking her, I kept on being amazed by how smooth and wet her pussy was. Even now over a decade later as I think back to the event I can still feel that silky smoothness.

This was not my first time getting to third base but I did not know anything about what a G-spot was. I do remember that in the position I was in, her on her back with her legs spread, with me kneeling by her right side my fingers kept feeling some ridges on the top inner portion of her pussy. While I was leaning over and kissing her. She seemed to be enjoying what I was doing because I started to feel her pussy rapidly contract on my fingers so I kept rubbing this area. As this is happening she start giving me a hand job. I was so excited that it was not long before I could feel the pre-cum on my dick, and saw it all over her hand.

It was right about this time that I was thinking that I did not have any condoms, but because I was so far gone in the experience I decided to just go in. I get on top of her and she guides me in to her soaking wet pussy. And in this instant everything changed for me. The moment before I was a virgin, and the next I was sinking my dick into this girl.

We started out in the missionary position, and as I’m pounding this girl at a good medium rate, she is loving what I’m doing, her head is turning side to side as she is biting her lips and grasping at the sheets, and it was not too long before I felt her pussy start to contract rapidly around my cock. I did not know what was happening so I stopped and waited for it to stop before I continued. I kept this up for a little while longer until I lifted her legs up to my shoulders. She was now moaning and groaning louder each time I buried my hard cock into her.

From this position I looked down and I was amazed by the amount of her girl cum that is on my dick! So this turn me on even more, so I keep pounding her pussy and it is in this position I can start to feel the tip of my cock hitting those ridges inside her pussy again. This happens when I enter her, and as I get balls deep I can also feel that my cock is hitting something soft and round at the back of her pussy. I don’t know if this is normal ( I think it is her cervix) but I’m not stopping for anyone!

I then move her legs from my shoulders and start to use my hands to push her knees toward her chest. This of course lifts her ass up and angles her pussy in a way that allows me to really hit her g spot. By this time she is going wild on me and I’m just pumping away to glory. Every few minutes her pussy would start pulsing, and she is shaking and I’m still thinking damn I’m having SEX!

We change position a few more times, one of the positions I move her into is to move my hand from the back of her knees and put her feet on my chest. I then use her feet and legs to hold me up and then transfer all my weigh to my hips. I tried this because I was tired from holding up my weight from before. This position really allowed me to use all 132 lbs. of my weight to drive me cock into that soft pussy. But by this point I was starting to feel the need to cum.

I moved out of this position after a while and got her into the doggy style position. I got behind her and just slid my cock all the way in. I wanted to cum, so I picked up the pace and started to fuck her quicker, each time I would pull nearly all the way out. By doing this I could watch as my dick came out of her pussy coated with her white girl cum and then watch as it plunged back into the soft wetness that was her pussy.

It was here that I learned that the doggy position was my favorite. I became so turned on by fucking her in this position, I started to feel my balls tense up and I knew I was going to cum. Because I was not wearing a condom and I did not want a kid, I waited until the last minute before I pulled out and grabbed the tip of my dick. I ran to my bathroom and let it all go into the toilet.

When I got back to the room she was lying on the bed with big smile on her face. She then proceeds to ask me “how many times I’d had sex before?” I told her “none, this was my first time!” She tell me to stop lying. I repeated to her again, no I’m serious this was my first time. I think that she finally starts to believe me, as I lay back down on the bed. She then decides to get up and use the bathroom, and this is were I got to see firsthand why she had a hard time believing me.

When she got up she had trouble standing. She had to hold onto the wall for a good 20 seconds before she could limp to the bathroom. She told me that her legs did not want to work.

After this we took a shower, and then went to the mall and hanged out for the rest of the day.

If given the chance I would go back and have her be my first again.

We started to date after this but, broke apart due to her cheating on me twice.

TL;DR

Met a girl while at a military recruiting office. Got her number, and a promise from her to help me study the basic military information you should know before going to boot camp. She comes over to my home a few days later. I give her a massage, and instead of studying basic military terminology, we started a human reproduction course. I did not know I was giving her multiple orgasms for hitting her g spot.

EDIT: changed formatting and spelling errors. EDIT : changed a few words around, added a question prompt and what happened with the relationship.