Indiscretions of [m]y youth: [F]irst time trying anal.

As with all of my tales of the transgressions of my past, I'd like to start off with a little bit about me. At this point in my life I was 18 years old and was probably in the best shape I'll ever be in. I had just finished playing football, and was still weightlifting and playing other sports for fun. At 5'10 and 170 lbs. I was solid and muscular. For those who care about cock size, I was nothing impressive, just an average 5.5". I didn't get a lot of girls while in high school, random hook-ups mostly and a few relationships that lasted about 2 years combined. However, as I was getting into my final year of school things started to pick up, a bit. This particular story is about the first time that I got to have anal sex. Bit long, but I have broken it up for you.

The beginning…

It was winter break from school and we were just coming up to Christmas, it had snowed pretty heavily a few days prior and hadn't melted away yet. My cousin Bill had been staying over a bunch, which wasn't unusual as he just lived a few blocks away, and we were bored…utterly. We had been calling people friends, girls, other friends, and hell, anyone who we could think of trying to find some party or just something to do. To our credit, we had procured some rum (stashed it between the bed and wall in my room) and were having "cokes." What we didn't have was anything to get into.

Eventually, we called up a girl named Angie. She told us that she had a friend coming over, who just happened to be from another school in town and that they didn't really have any plans. Bill and I started working the game. Though, if I am being honest, the big selling point for her was that we had some liquor.

I had dated Angie for a short time previously and since she had developed a bit of a reputation for being a little easy. She was 18, as well, and she had a body built for sex. She was 5'4, about 120 and had a classic hourglass shaped figure. Angie had developed a terrific body and sported a perfect pair of C-cup breasts with big, round nipples, but what usually caught my attention with her was her ass. She had an ass that just begged to be grabbed and spanked. Much to my chagrin, Bill said he wanted her, so I was not going to make a play there. That left me playing for the unknown girl, Mandy. I didn't know much about her other than what Angie had told me. She was "cute," eighteen, and had big boobs (Angie knew what was up). We got a few movies out and I picked out something that was in my mind good. It had a bit of nudity and was fairly long. I figured even if the night went south at least I would have something decent to watch.

As they arrived we all headed up to my room to watch the movie. I was kinda nervous and wasn't paying attention to anything in particular. Just headed to my room on the double (so young and inexperienced). When we got up there, I finally noticed Mandy. She was actually cute in the face, and had dark brown hair that was ridiculously curly that went down to her mid back. She was initially covered up with a heavy jacket, but as it came off, I got the first surprise of the night…she had a phenomenal body. Mandy was about 5'6, her stomach was lean and narrow, not supermodel skinny, just well toned. Her stomach accentuated the rest of her features, which were a tight, muscular ass and and a pair of full D to DD-cup breasts. Even with her completely covered, I could tell this girl had some tremendous assets.

The setup for the main event…

I started up the movie and we all took seats on my bed. Initially we were all talking and having a drink, but we soon started to get comfy as the movie previews gave way to the movie. Bill had already started hitting on Angie, though it looked like to a somewhat limited effect. I was just laying back and joking with Mandy. I threw out a compliment here and there, but mostly I was just trying to break the ice.

After about a half an hour or so of the film I could sense that the tension had built up. In retrospect, I think everyone knew what was going to happen, but everyone was hesitating to make the first step. Then the dam broke, Bill went in for the first kiss with Angie. From that point on it was just them making out, and not silently. Mandy and I were loosely spooning, mostly to keep our backs to the scene behind us. The combined sounds of their making out, along with this girls succulent body so close in proximity to mine and the general horniness of a male teenager, led to my cock starting to stiffen.

I tried to casually re-adjust a few times to get things situated comfortably, and somewhere along the way my hand touched Mandy's curvy ass. She looked back at me, and I just kind of apologized. I told her I was a little uncomfortable and was just adjusting position. She didn't buy that. She kept looking at me and that's when I went in. I just kissed her. Nothing passionate and long. Just a quick kiss. That led to the a flurry of the passionate, deep kisses where her full lips parted and our tongues darted and swirled around each others mouths. I had placed my hand on her hip and I was slowly moving it higher. She stopped me though and broke the kiss. She whispered that she didn't want to make out or do anything else directly beside my cousin and her friend. She said it would be weird. Eh, whatever. So I convinced her that we should get down to the floor and take one of the blankets and several pillows. We could get comfy there and they would really be able to see us unless they were looking. Maybe it was just being horny herself, but she followed my line of reasoning.

Game on….

I very quickly noticed two things once we had gotten to the floor and made ourselves comfortable. One, Mandy had managed to undo her bra without me seeing, and two, I didn't have any condoms. We resumed where we had left off, still spooning, but now with her ass grinding back and forth on my maddeningly hard erection. I had left all pretense that I was trying to go slow behind. I slid my hand up under her shirt and grabbed onto her left breast. It was so big! Her nipples were hard and very thick, about the size of a dime in diameter. As soon as I started caressing her nipples she turned her body to lay on her back. I could tell she was giving me easier access and I also took that as an invitation to raise her shirt. As the shirt finally crested over her magnificent globes, I finally got to see the puffy areola and thick, erect nipples I had been teasing with my fingers. I quickly put a nipple into my mouth and flicked my tongue across. I continued playing with her other breast in my other hand. They were much more than a handful and were firm to the touch.

During my ministrations to her perfect breasts she had slipped a hand down to my crotch and was gripping my hard cock through my pants. She was slowly rubbing me and it was sending pleasure to every nerve ending. At one point I groaned so deep that I let go of her nipple altogether. I quickly started unbuttoning her jeans and as i tried to slide them down she asked if I had a condom. (see above for the answer) I told her that I didn't and she said she wouldn't take the chance on getting pregnant, but that we could still play around.

I was utterly defeated. Then in one glorious moment a thought came to me. "Can I put it in from the back?" She looked back at me, her face looking somewhat confused, and then I clarified somewhat, "Have you ever tried it from the back?" She quickly comprehended and said that she hadn't, but that we could try it. I knew nothing about anal sex outside of porn. But the one thing I did know was to use lube. I didn't have any lube, so I was determined to use a lot of saliva. We were trying to mess around without the other two on the bed seeing and now I was going to need saliva on my hardened cock. I told her to give me a sloppy, wet blowjob…just for a second or two.

Mandy ducked under our shared blanket and grasped my penis in her right hand and started to kiss the head softly. She gave small, quick licks to the coronal edge of my glans – swirling her tongue and then giving another kiss. After a few passes and her hand stroking up and down the shaft, she took me into her mouth. My stiff prick was enveloped by her warm, wet, and inviting orifice. I was straining not to make a sound as she took the shaft down inch by inch until she reached the base. Her head bobbing back up for a quick second and then bottoming out again moments later. She was getting me close, and I wanted to cum. I could feel every movement of her tongue, every suck from her lips and mouth, and god I wanted to spurt my seed down her throat. Yet, I had other plans that I really wanted to play out.

I reached under the covers and pulled at her hand, trying to signal for her to come back up. When she finally understood she gave one last deep kiss to my cock and came up without sucking the saliva back off of it. Unbeknownst to me she had also taken her jeans down along with her underwear. She had pushed them to about her knees. I couldn't see her ass, but once she laid back down beside me, I could feel this curvy, muscular ass against my swollen, saliva-covered member. I whispered into her ear to spread her ass. As I felt her cheeks spread apart i gripped my cock and started stroking the edge of her tight little hole. I pushed in a little and couldn't quite fit the head in. So I continued slowly pushing the head in and out, hoping that she'd loosen up. After a few minutes I had gotten my glans past the opening and was feeling the pressure of her anal sphincter. She was so tight. She let out little pained gasps as I continued my soft assault.

Now that the head was in I was free to use my left hand again so I had been alternating from playing with her nipples to rubbing her sopping wet pussy. I noticed more than a couple times during this process that as my hand made its way down from her nipples that her hand was there as well. She was fingering herself and coating her clit in her juices. Again, I was not overly experienced at this point in my life, and as I was attempting to finger her, she took my hand and guided it to the sensitive little nub and started making me rub in a slightly oval motion.

Suddenly, I felt my cock pop in past her sphincter. She gave a little wince and a groan. I asked if she was ok and she told me that she was. She said it hurt a bit. I asked if I could keep going and she said to hold on. I stayed motionless with the exception of pulsing my cock. A few moments went with me still rubbing her wet slit and my cock barely inside her ass, when Mandy did one of the most pleasurable things I had to that date ever felt. She started tightening and releasing her little anal ring on my cock. I couldn't take it, it felt so fucking good, I started to move my hips. She told me to go slow. As I started to push in, she tightened around my cock, it made her wince again. The next time that I started to push, she pushed out instead. At that point, I found out that I loved anal. As I pushed my throbbing cock into her, she pushed out with her anus. Nearly all of my cock plunged into her. I was all but an inch from being completely buried in her. She didn't wince, nor did she make the tell-tale sounds of pain; this time she moaned, softly.

From that moment she started moving her hips on her own, I just sat back and let her take it at her pace. She was bottoming out on my cock with every few movements, but mostly she kept to the point of where my head popped in and out of her sphincter. As she started to pick up the pace, I started to push my hips forward. Now each thrust was bottoming out in her ass. My cock was devoured by this perfectly tight and warm hole. All the while we were trying to keep from being noticed.

I had abandoned trying to play with her pussy and just kept my hands on her full breasts. I would pinch her nipples here and there, but I was nearly completely focused on fucking her ass. I could feel my orgasm building. I think she could tell, too. She started squeezing her ass around my cock as I would pull back to her anal ring. It felt like a sucking motion …it felt amazing. Just as I was about to cum, I whispered in her ear again, "Can I cum in your ass?" and she bottomed out hard in response. I exploded. I could feel pulse after pulse of my seed shoot deep into her ass. I had to bite my own arm to stop from yelling out loud. She just kept fucking, pushing her ass back and pushing my cock as deep as it would go.

After the orgasm had subsided, my cock began to soften. I felt drained and I was utterly satisfied. As I started to slip out of her ass, she could feel my cum start to leak out. She carefully got her panties and jeans back up over her ass, and I got my cock back in my clothes and we just laid there until the end of the movie.

Interestingly, she never excused herself to the restroom. Even when they were leaving, not once did she go to clean up. I asked her about it the next time and she told me that I was leaking out of her all night. More interesting, was that she wanted to feel me leaking out of her again.

Source: reddit.com/r/gonewildstories/comments/3ytivp/indiscretions_of_my_youth_first_time_trying_anal