My first time – part 3

14 years ago I posted a couple of stories from my first sexual experience, which had been about 6 years before that. I am finally continuing the story…

A guy named suckboy who I had met in an AIM chat room had convinced me to let him suck my dick for 50 bucks.

We met up, he came over to my parents house after school one day and suck my young dick off until I came in his mouth.

After I got up and was walking around naked he got some more ideas but we did not have enough time…

Fast forward a few weeks, and we found the opportunity for me to come to his house.

We wasted no time and before I knew it I was naked on all fours. He slid underneath me and began sucking my dick and rimming my ass. I’d never experience something so amazing.

For too long I told him I was going to come and he took my whole dick in his mouth and swallowed my load.

This happened several times over the next few months. I always felt a bit of shame afterwards but I enjoyed the feeling I got and the money he paid me.

Fast forward a few more months… He had graduated from the local University and moved out east. I didn’t know until he had already left and I was sad at the loss of my dick sucking ass eating slave who is willing to pay me lol.

He emailed me and let me know that he had moved but he would be visiting at the end of the summer for some reason. I really don’t remember what. He said he would be getting a hotel room and would like to see me. I was all about it.

Has it got closer to his visit he asked what I would like in exchange for our usual fun and I told him that a couple packs of cigarettes and a $50 bill would do just fine. But I got the sense that he had other ideas, and indeed, he did.

Finally he emailed me and laid it all out. He wanted to fuck my tight little teenaged asshole.

I didn’t know what to think… I was certainly intrigued though.

Finally I agreed to it under the following conditions:
LUBE. Lots of it. A sex doll. I picked it out. $150. And he has to stop if I say so. All was agreed And I excitedly awaited his visit.

The Day of the tryst, I snuck out under the guise of participating in a community service group of which I was a member… Of course the only community that was getting serviced that day was suckboy.

I drove to his motel and anxiously awaited him to text me the room number. As soon as he did I left out of the car and quickly walked to that door. He had the door cracked and I went on in. On the dresser next to the TV I saw the box containing the sex doll, and an envelope with $150. On the nightstand next to the bed was the biggest bottle of lube I’ve ever seen. He already had his pants off and was stroking himself. It wasn’t a huge dick thank God, but it was at least average. About the size of mine. I started to shake with anxiety.

Sensing this, he came up to me, took my clothes off, began to kiss my nipples and then melt down and started sucking my dick which was semi-hard. In no time at all I was feeling much more relaxed, and more than that, I was excited.

In short order, he moved us to the bed and put me in doggy position, laying on my arms with my ass in the air. He grabbed the big bottle of lube and positioned the spout right into my asshole and squirted. Lukewarm liquid filled my anus and dripped out. It sort of took my breath away.

I looked back and saw that he was now rubbing lube all over his incredibly erect penis. I don’t know that I had noticed it being that big before. Suddenly it looked long and thick.

He was obviously very excited. So excited in fact that in one breath he asked if I was ready and before I could even really get a response out, I felt the head of his hard dick pressing against my sphincter. I felt the incredible pressure, and wish that he would try using a few fingers first. I started to say that when THWOP! In he popped. I held my breath and unwittingly clinched my ass around his dick. He let out a surprise and satisfied moan. The next 90 seconds are a blur.

He grabbed my hips, and pulled me towards him as he thrust deeply into my ass. Then with little warning and despite my somewhat unconscious pleas for him to stop, this 20 something year old man spent the next minute and a half taking my virginity and destroying my tight little asshole.

He pounded my ass with reckless abandon. At some point he fell onto my back and continued to pound deep, hard, and fast. I could sense that he wasn’t going to last very long. His pace quickened. His breaths were shorter and closer together. He was moaning. He was telling me what a great ass I had and that there was no way he could stop. How he wanted to fuck me since The first day he sucked my dick. He went so hard and so deep and so fast I felt like my ass was going to just break apart. As he climaxed I felt his pace slow but his thrust were just as deep and hard. Suddenly, with a very deep grown, almost a growl, I felt his cock twitch in my ass and his cum spewed forth like a fountain, deep into my teenage hole.

He relaxed, I could feel his breath on the back of my neck. Slowly it returned to a normal pace. He slowly pulled himself up off my back and I felt his now shrinking cock plop out of my wrecked hole. Then an excited gasp escaped from his lips and he told me to leave my head down, lift myself up and look underneath me. Behind me I saw his dick with cum and lube dripping off onto the hotel bedspread, and between my face and his dick was my leaking asshole. Cum and lube seeped from my asshole.

He patted my ass and told me I better go get cleaned up. He directed me to the bathroom where I sat on the toilet and tried to push everything out. I then jumped in the shower and bent over and spread my cheeks to let the warm water clean me out.

After 5 minutes or so I got out and towel off. I went back into the bedroom and saw that he was laying on the other bed, as it was a double room, stroking his dick. Straight to the point, he asked if I thought I could do that again. He must have seen the look on my face, which was of shear astonishment as I recall, as he quickly dismissed his own suggestion and asked if I was okay. I said that I was. I was feeling so many emotions though. Excitement, shame, regret, repulsion, anger, and maybe most of all, I was horny.

I didn’t cum during his pounding of my ass, as I’d heard was possible (and kind of seen in the movie Road Trip). Sensing this he motioned me to approach the bed.

If I’m being 100% honest, my dick was semi-hard the entire time I was getting fucked, and had remained so while I cleaned up. I had slowly stroked it the whole time.

He immediately took me in his mouth and started sucking in a way that I can only describe as grateful. He owed me one.

After a little bit I climbed onto the bed and on top of him, in 69, with my ass in his face. I was hoping he would rim me but having just deposited his load into the same hole, he seemed uninterested. He did start sucking on my cock from that angle though and it felt incredible. Looking down I noticed that he had cleaned up his dick and it was mostly hard, just a few inches below my face. He didn’t ask and neither did I, I just took him in my mouth and began moving my mouth up and down. He seemed to be enjoying it, as was I.

His enjoyment however translated into an even more intense sucking of my dick and In short order I fell an orgasm coming on. I moaned, My dick twitched, and I deposited a big load right down his throat.

Immediately feeling some sort of shame, I left up, put on my clothes, grabbed my rewards, thanked him, and left. I jumped in my car and peeled out of the lot, my big V8 rear wheel drive coupe swinging sideways as I pulled onto the frontage road and blasted towards the highway.

Again I was experiencing a ton of different emotions, but at that moment I was hyper fixated on my very loose rear end and how it felt like all my organs might fall out as I drove.

I got home, went up to my room, blew up my new sex doll, grabbed a bottle of lube and started going to town. It didn’t feel great but it was fun.

The next thing I knew however, one of my parents was home and started up the stairs to my room, I jumped off the bed, pulled up my pants, pulled the doll off and slid her under my bed. My mom stood in the hallway and talked to me about something obnoxious and benign. I could sense that she was not buying my story about community service but I took a hard line and held firm.

Soon enough she retreated to the main floor and not knowing what else to do, I took a pen and poked a hundred holes in my brand new blow up partner.

Over the years since I have occasionally received an email from suckboy, And he had wanted to get together but I never responded with any interest and have not seen him again. The last I heard, he had gotten involved with the closeted gay son of a New Jersey Mafia Don. He sent me an email of details of his relationship and while I found it interesting at the time, I thought that I probably shouldn’t keep that information, so I deleted it and have not heard from him since.

I think about my time with him occasionally and it’s mostly positive. Looking back I realize how inappropriate it was for a 20 something year old grad student to have a sexual relationship with the sophomore and junior in high school but I did have a good time… Since then I have enjoyed a great deal of illicit behavior – more to be shared here – But often is not I think about that guy pounding my ass with such excitement that he blasted his cum into me after less than 2 minutes. Sometimes it bothers me a little bit but most of the time I don’t think about it long enough to have a reaction one way or the other.

One thought that does persist though is that he got caught by the mafia dawn fucking his son and caught a bullet between the eyes. Who knows?

Good to be back. See y’all next time.