It was an experience that I will never forget. It has already been three years and I can vividly remember the details. I relive the night almost every single day.

It was a Friday and it was my friend, Jeni’s birthday. I have known Jeni for over ten years, and was pretty pumped up for her 21st celebration. Being a good friend that I was, I offered to be her DD for the night. The plan was to get dinner and hit up a friend’s hotel room near a club where we had a bottle reserved.

Jeni and I were never very close, but we hang out regularly with a bunch of other friends. She was shy, insanely cute, and recently single. I’ve always had a fantasy that involved both of us naked, but little did I know that was about to come true.

She is Indian, exactly 5 ft, and extremely petite, weighing at just under 100 lb. I know this for a fact because we weighed her during a drunken debate at the hotel.
She has long dark hair and breasts just begged to be grabbed and sucked. I am not very good at sizing, but I would say she has a solid B cup. I wish I could post a picture of her because words really do not justify.

There were five us at dinner, and before the food arrived, we already ordered her a glass of wine and a white russian. By the time dinner was finished, she had already downed a second glass of wine and half a cranberry vodka.

We arrived at the hotel where more of our friends showed up. I was mingling with some of the other guests but numerous cheers and shouts of “Happy Birthday Jeni!!!” was enough to tell me that she was going to end up drunk as fuck.

It was about 10:00 PM, 3 hours and numerous drinks later, that we decided to go to the club. Needlessly to say, the alcohol already had taken a hold of Jeni, and she had trouble walking in a straight line. Being the gentleman that I am, I offered to hold her steady while we walked into the club. As I took her arm, I got a whiff of her perfume and something stirred in my pants. She smelled so DAMN GOOD! Her aroma was so arousing that I had to shift my junk around with my free hand, hoping that no one had noticed.

As the night progressed, and she got more and more drunk. Watching her dance in that tight white dress made me incredibly horny. She was swaying her hips, grinding up against her other girlfriends, and at one point bent over so low that I caught a glimpse of her white thong. I had a hard time hiding my boner in the slacks that I was wearing. As I finished my second beer of the night, Jeni came over and sat down next to me and pressed her face close to mine, “Wow! I am having so much fun!” she shouted over the thumping music. “Thanks so much for coming!” She gave me a big hug and pressed her tiny body into mine. My boner nearly ripped through my pants as I inhaled her intoxicating scent. It was everything I could do not to just rip off her dress and fuck her right there in the middle of the club. However, to my disappointment, one of her girlfriends pulled her away to the dance floor.

Soon it got to the point where she could barely keep her eyes open and was leaning every which way. Regardless of the fact that we paid over $1,000 for a table, the bouncer told us that we needed to take her out because they could not have her falling asleep in the club.

It was already 1:30 AM and everyone was already pretty wasted and most of our friends decided to go home. After saying good-bye to everyone, I guided Jeni back to my car. She had difficulty walking, and was stumbling all over the place. However, I managed to get her into passenger seat, thoughtful enough to recline the chair all the way, and we started the drive back to her house.

Once I got on the freeway, I looked over at Jeni to check on her. She was on her back, with her legs spread open and completely passed out. I noticed that her dress was hiked up enough to reveal her thong and I immediately got hard. I leaned down and asked, “Jeni, how are you feeling?” I got no response which made me bolder. I asked her once more, shaking her gently and still got no response. I slowly slid my right hand from her arm down to her leg and stroked it lightly. I slowly inched my hand between her legs, prying them apart. My hand brushed the front of her panties and I felt the warmth between her legs.

Unable to concentrate on the road at the same time, I withdrew my hand and managed to get home without having my boner rip a hole in my pants. Parked in the driveway, I reached over and started to rub her pussy through the thin, silk cloth, gradually increasing the pressure. Amazingly, Jeni was knocked out cold and did not even flinch as I pushed her panties to the side. To my utter amazement, her pussy was slick with juices. I gently rubbed up and down the opening of her pussy, spreading the juices all over the outer lips.

I decided that I had to get her to my room. Reluctantly, I pulled away from her pussy, and exited the car.

She still couldn’t walk so I carried her into my house. I dumped her gently onto my bed and I turned on the light. She looked amazing laying there in the middle of the bed with her dark hair spread all around her.

My heart was racing. I finally had her to myself. I crawled onto the bed and kissed her on the lips. I worked my tongue into her mouth, as I reached up and squeezed her left breast. I slowly glided my hand down her body and reached and rubbed her pussy through her panties once more. Her juices had soaked through her panties, and the silk material was damp with her juices. I hiked up her dress and slowly peeled away her panties revealing a smooth, shaven pussy that was glistening wet. I couldn’t help myself as I pushed her legs further apart and brought my mouth close to her pussy. It smelled so damn good. I stuck out my tongue and slowly licked the outer lips. First the left one, then the right one. I then licked along the middle, circling the entrance to her vagina. Pushing my tongue into her tight pussy, I massaged both of her breasts with my hands, squeezing them through her dress and bra.

Pulling my face away from her pussy, I slowly pushed my index finger into the opening of her pussy, surprised at how tight it was. I began to finger her, slowly at first, but gradually increasing the speed of my thrusts. By now, it was getting very wet, making quiet, squishing noises every time my fingers entered her. I managed to slip both my index and middle finger into her pussy. The two digits slid in easily, and I curled my fingers upward and started to rub at her g-spot. Jeni gave a slight moan as she shifted, opening her legs a little wider as I continued thrusting.

After maybe 30 seconds, she twisted her body away. I stopped and looked at her face, but she was still passed out cold. I decided that I needed to see her fully naked. After shaking her slightly to make sure she was still knocked out, I rolled her on her stomach, unzipped her dress and slid it off of her. I unhooked her bra, and flung it on the floor. I realized then that it was the first time I got to see her ass. Holy shit, I almost ejaculated right then and there. It was the hottest ass I have ever seen. Not only was it small, just like the rest of her, it was a perfect, firm, bubble shape. I spread open her cheeks and the sight of her small, puckered ass hole made my heart race even faster.

I stuck a finger back into her wet, sopping pussy, and gave it a few thrusts. When I withdrew it, I saw that it was glistening with her pussy juice. I then placed my finger at the entrance of her asshole, and slowly pushed. It was extremely hard to get in, and I had to push pretty hard. I finally got my finger into the first knuckle and felt her ass tighten up instinctively. I slowly worked my finger in and out, enjoying the warmth of her asshole.

After awhile, it got a little dry and I pulled my finger out. I rolled her onto her back and got undressed. As I pulled off of my boxers, my 7” cock sprung to attention. As I got onto of her, I saw her breasts for the first time. They were perky, with tiny nipples and a nice, dark areola. I flicked her right nipple with my tongue, and then covered it with my mouth, sucking it gently. I did the same with her left nipple, but as I stroked my cock, I started sucking on it harder.

My mouth never leaving her nipple, I pushed her legs open and positioned myself at the entrance of her already wet vagina. While sucking and nibbling on her breasts, I rubbed the head of my penis up and down her wet slit. Jeni let out a small sigh as I gently pushed my dick into her wet pussy.

Oh my God, the feeling was incredible. I started thrusting slowly, afraid to wake her up. But looking at her perfect body, and watching my dick slide in and out of her pussy, turned me on so much that I began to thrust faster and harder. The bed started to rock as I held up her legs and started pounding her pussy as hard and fast as I could. Jeni started moaning and I guess she woke up a bit because she tried to push me away. However, I was already inside of her and no way was I going to stop. I hooked my arms under legs and held her wrists above her head as I continued to slam into her pussy.

The loud slapping noises reverberated throughout the room as I fucked her pussy. I felt her struggle against my grip, but she was still unaware of what was really happening. I leaned down and stuck my tongue deep into her mouth and was surprised to feel her tongue weakly meet mine. However, after a few seconds, she turned her head away and I resumed pounding her pussy.

After a few minutes, I felt an orgasm coming and I quickly stopped and pulled out. As I released my grip on her wrists she turned away, still asleep, and almost rolled off of the bed. I quickly caught her and pushed her back towards the middle of the bed. I then got an idea.

I positioned her so her head was hanging off of the side of the bed while still on her back. I then knelt/squat above her face and began stroking my cock which was covered in her juices. Aiming for her half-open mouth, I pressed my dick into it and was immediately greeted by her limp tongue. After a few thrusts into her slack mouth, I again felt an orgasm coming up quickly. This time I didn’t fight it; groaning as I shot three big loads into her mouth. The cum rapidly spilled out the side of her mouth, dripping into her hair and onto the side of the bed.

Apparently that was too much because it was then that I heard a gagging sound and a second later, Jeni threw up on the ground. The smell immediately hit me and I stepped away still naked to clean it up, wiping the vomit and cum from her face and the floor.

After the puke was cleaned up, I looked at Jeni, now curled up on her left side with her back towards me. My eyes instantly fell to her luscious ass, and my cock started to harden. I rolled her onto her stomach and wet my index finger and gently rubbed her puckered asshole. Receiving no response, I pressed harder and harder until the tip of my finger entered her tight orifice. I started probing deeper, and once I got to the first knuckle, she stirred and mumbled something. I started to thrust my finger in and out of her ass, slowly at first. As I started increasing the pressure and speed, her arm shot up and she tried to push my hand away from her asshole. It was getting dry so I pulled out.

My dick was already rock hard and i really wanted to fuck her in the ass so I went to the bathroom and retrieved a few bottles of lotions that they provide at hotels, and returned to the bed. I positioned Jeni so she was on her left side, with her knees curled up to her chest and her butt just barely hanging over the edge of the bed. I emptied half a bottle of lotion onto my palm and rubbed it all over the entrance to her little brown asshole, and the remaining half of the bottle went all over my rock hard dick.

While stroking my cock, I thought to myself, “Wow, I can’t believe this is really happening.” Placing the tip of my cock at the entrance of her anus, I pushed. Her asshole was so tight that the first few attempts failed. My cock would slide to the left or to the right, into her pussy; her anus refusing to accept my throbbing member.

I decided to loosen her ass up a bit and stuck my middle finger into her ass. It slid in easily with the help of the lotion and I fingered her for a bit. I then added my index finger and pushed back into her tight hole. I managed to get to the second knuckle when Jeni woke up and yelped in pain.

“Owwww! That hurts!” She exclaimed as she tried to sit up and push me away at the same time.

I firmly held my two fingers into her ass as I pushed her down with my free arm.

“Shhh, it’s ok. It’s ok.” I told her.

Still in her drunken stupor, she asked “What are you doing?”, flopping back onto the bed.

“It’s ok.” I repeated as I pushed my two fingers as far as they would go.

She tried to jerk away but I firmly held my fingers in. After a few moments of fighting, she relaxed and it seemed like she passed out again.

I decided that it was time.

I withdrew my fingers, and saw that her asshole had barely enlargened.

Stroking my dick once more, I once again positioned myself at the entrance of her asshole. This time, I aimed carefully and pushed forward firmly. I felt her sphincter tighten at the pressure, but gave way as I pushed harder.

The head and a good 4 inches burst into her tight asshole. That definitely woke her up.

“Owwww! FUCK!” she shrieked in pain, turning onto her stomach as she tried to crawl away.

With my dick still in her asshole, I gripped her waist with both hands and held her down as I started to thrust in and out of her tight anus. The feeling was incredible. As I thrust in and out of her, she tried to push the invading cock out by tightening her sphincter. This in turn made the feeling even more arousing, and I pumped her asshole even harder.

By now, she was crying in pain, begging at each thrust to stop the torment.

“It’s ok Jeni. It’ll be ok.” I kept repeating over her cries.

After a few minutes, I felt myself coming close to an orgasm and I stopped thrusting. I wanted to enjoy her asshole a little bit longer.

I pulled out quickly, my cock sprung out with a wet pop, and she yelped and immediately curled up in the fetal position, sobbing.

I crawled onto the bed and pried her arms and legs open, positioning her so she was on her back.

Grasping both of her ankles, I pushed them towards the headboard so her knees were by her ears, and her ass was up in the air, fully exposed. I looked at her asshole and I could see that it was pink and very moist from the lotion and the pre-cum.

She protested and struggled weakly as I gripped both of her ankles with my left hand while stroking my stiff cock with my right, guiding it to her asshole. I was standing over her now, and positioned the tip of my cock at the entrance to her ass. I gave one look at her tear-streaked face and plunged the entire 7 inches of my dick into her ass.

I have never heard someone scream so loud before. She gave an ear-piercing shriek as I bottomed out. I held my dick deep in her asshole for a few seconds, before I started pounding her asshole mercilessly, her legs still pinned above her head.

“OH GOD STOP!” She screamed, “IT HURTS SO BAD!”.

This time I didn’t even bother to answer her as I continued to thrust in and out of her asshole.

“STOP!!! STOP!!!” She begged over and over again.

I pulled my cock completely out, and plunged it back in again, hard.

Jeni gave a gut wrenching cry, “UUUGGGHHHHH!”

I resumed thrusting into her, squeezing her breasts and inhaling her scent.

The sight of her little body balled up and taking a cock in her ass was too much for me. I gave one last thrust, burying my cock deep into her asshole, and shot the largest load of my life into her colon.

I released her ankles, and collapsed on top of her, my cock still lodged into her asshole.

She whimpered as she tried to roll away. I didn’t try to stop her, and my semi-limp cock slid out of her asshole with a wet sucking sound.
Jeni rolled onto her side and resumed her fetal position, sobbing softly into a pillow.

After catching my breath, I got up and looked at the damage that I have done. There was cum, lotion, and some blood leaking out of her asshole. The fluids had mixed into a pinkish white color, and had dribbled out of her ass and left a small damp spot in the middle of the bed sheets.

I got some wet paper towels and cleaned Jeni up. Every time I wiped near her asshole, she jerked and winced in pain.

After I was done, I gently shook her and asked, “Jeni, are you ok?”

I got no response and I realized she was once again knocked out cold. I smiled to myself and carefully dressed her; sliding her thong back on and with some difficulty, zipped her small dress back up. I carried her to the couch, and covered her with a blanked and I went back to my bed. Sleep came to me in a matter of minutes.

For those of you who wondered what happened next well I woke up in the morning and she was still asleep on the couch. Now that I was sober, I was scared that she would remember all of the details from last night. I woke her up, making sure she was ok, and walked her out to her car. She half limped/half waddled the whole way there.

“What happened last night?” she asked me when we got to her car.

“What do you mean?” I asked, my heart pounding.

“I don’t remember anything after leaving the club. And when I woke up…” she trailed off.

“What?” I probed.

“Well…” she said, one hand behind her, “my back was very sore.” she finally said.

I smiled to myself, knowing the true source of her pain.

“I have no idea. I wasn’t with you the whole time. Maybe you fell when you were drunk.” I said.

“Yeah, that’s probably true.” She said, rubbing her butt. “Well, thanks for driving me home and taking care of me. I hope I wasn’t too much trouble.”

“Oh no, you weren’t.” I assured her. She gave me a quick hug, and limped to her car.

Yeah, I know. I was fucking lucky as hell. I look forward to the next time I am the DD for her again.

---