Anal Sex Stories
238. Man's Story: Backdoor Birthday (7/17/04)
A couple of years ago, I was in a relationship with a married woman who was 20 years older me. This woman was great in bed and gave fantastic head, but would never let me go up her ass.
The day before my birthday, she rang me and told me to come around the next day as she had a "birthday treat" for me. I was able to guess what it might be so I was almost hard with anticipation when I rang her doorbell. I was completely hard when she opened the door wearing only stockings and suspender belt. She dragged me into the house, got on her knees and blew me until I shot off over her tits.
She gave me a while to build back up again, and then sure enough, she produced some lube, and smeared it generously on my cock. She went on all fours, I applied a little lube to her ass, and inched my way in. She gasped with pain at first, but it soon turned to moans of pleasure as pumped away in her tight, virgin asshole.
I shot my load in her, and pulled out to watch it come back out of her gaping hole. I really enjoyed my birthday present, and she must've too, because I went in her ass a few more times after that.
229. Woman's Story: A Great Massage (6/29/04)
I lived at the beach for a summer when I was in college. I worked at a restaurant with this really cute guy, Kevin. We hung out all the time, but just as friends. He always rubbed my shoulders and said he gave great massages. We were hanging out drinking at the beach and we went to my apartment to refill the cooler. He started rubbing my shoulders, saying what a great massage he gave. I led him into the bedroom and told him to prove what a great massage he gave. He put lotion on my back and did give me a great massage. I felt him start to pull down my bikini shorts and didn't stop him. He rubbed my ass and legs and slowly spread them. He teased my bum hole and I got really wet and excited. Then he slid a finger into my pussy, then two. I just let him go. Then he pushed a finger in my bum and made me have the most unbelievable orgasm. He kissed the back of my neck and whispered, "I told you so." Then he left and returned to the beach. I had to take a couple of minutes and then went back too.
195. Man's Story: Ass Passion (12/10/03)
My wife and I love to watch X-rated movies when we really want to have a passionate encounter. One night after we enjoyed our movie I started to lick her cunt. She was really turned on and I expected that. As I was licking her, I let my tongue start to explore the area between her ass and her pussy. She began to go absolutely crazy. She got so wet it was incredible. I began to lick her ass while I played with her pussy with my fingers. I thought maybe she would be put off and ask me to stop, but instead she lifted her ass in the air and spread her legs, making her beautiful anus fully available to me. As I was sticking my tongue in her ass, she had one orgasm after another. She told me to put my finger in her ass and to lick her pussy. That produced similar results until she couldn't stand it any more and told me to go get the Astroglide. I went quickly to the night stand and got the small bottle of lube and she told me to pour it on her ass. I ask her if she wanted me to put two fingers in her ass, and she said, no, she wanted my cock. I was so excited that I think I came as my cock was going in, which made her ass really slippery. I came but did not lose my hard on and fucked her until she passed out. It was absolutely the most intense lovemaking session we had ever had. We try to repeat it about once a month, and my tongue in her ass is a weekly event.
22. Woman's Story: First Time Behind
It was the first time my boyfriend had rented a hotel room for us, and I was sure that he wanted to fuck more than just my pussy. As we began the foreplay, I knew immediately that he was going to fuck me in my ass. He began sucking on my tits holding me tightly with one arm around my waist while his other hand was finger fucking me. I was extremely wet. He then got up and proceeded to lay on top of me, holding both my hands above my head with one hand. He softly began kissing my ear and as he did that, his other hand moved down my ass. With his legs, he spread mine slightly open and then with his finger searched for my asshole until he found it. I was startled and he began to whisper into my ear..."shhhhh, you're going to love it". He then stuck his tongue into my throat and wouldn't let me move. He moved his finger all around my asshole, until I finally let out a moan. That was when he let me go.
He turned me over and I quickly got on all fours, thinking he was going to fuck my pussy, but all of a sudden, I felt his lips and the heat of his mouth on my butt. It was the best feeling I had ever had. He stuck his tongue in and out of my ass, while his fingers were getting wet with all of my juices. After a few more pleasurable moments, I let out a scream when I felt his huge cock going into my tight, virgin asshole. It kind of hurt, but after a couple of seconds, I started to really enjoy the massiveness of his dick fucking my asshole. I was extremely turned on and I felt so dirty, but I loved it. He finally asked me if he could come inside my ass and I let him. It was great. He fucked me in the ass all night long. I think now I'm addicted to assfucking.
36. Man's Story: First-Time Anal
The first time I ever fucked a girl up the ass was in my Senior year of high school. We had been having vaginal sex and oral sex for a while before then. Anyway, one night we were making out when I told her we should try something new. She agreed with a look of wonder on her face. I went into the bathroom and got myself all lubed up. When I returned (lube in hand) I told her to get on all fours. She did as directed and I moved in from behind. A quick squirt of lube on her asshole was all it took to get her attention. When I put my cock-head on her asshole she made an uneasy groan. I slowly popped it in and got the whole shaft in. When I started pumping she made moans of pain. I asked her if she wanted to stop, but she said "No, I have to get over the pain". After a few minutes of getting her ass used to being full, the cries of pain turned into moans of pleasure. She rubbed her clit as I ass-fucked her for about 15 minutes. We both had huge orgasms. For another good 6 months (until we broke up), I'd do her up the ass almost every other day. I can still remember how her little pink hole looked with my cock ripping it at the seams.
42. Woman's Story: First Time Anal
I have always been this adventurous woman when it came to sex and almost anything else, but anal sex scared me and seemed somewhat forbidden. I knew so many people who had done it before, but for some reason I remained an
anal virgin until I met the right person to trust and I knew I had to try.
He leaned me forward over the rail. All I could see was the ocean below us as he raised the skirt of my dress and ripped off my panties. He was so hungry for this. He had waited so long. I felt his fingers go deep into my wet cunt and he was pumping me getting his fingers so creamy. He took his fingers out and started to massage my asshole. It was so hot! I tensed at first because I was scared, but then I felt his fingers slide right in. "Oh God!" I screamed. It was the most intense feeling ever. He was sliding his fingers in and out of my ass so deep. He pulled the fingers out and I felt his cock head press against me. Now, I was really scared but at the same time crazy for him. He grabbed my hips and plunged deep into me. I screamed like I never have before as he pumped me against the railing. His cock felt huge! There was no pain only pleasure as he fucked my ass. He pumped me so hard until I felt him start to tense and I told him I wanted him to fill my ass with his cum. Just hearing me say this made him rip his load deep into my asshole and I came with him. It was more intense than anything I have ever experienced.
50. Woman's Story: Wedding Night Plan
My fiancée wants to fuck me in the ass. I never really though about it in any way, but he has started climbing on top of me whenever I lay on my stomach. He rubs his dick against the crack of my ass, and it starts to get me real excited. I rub my ass up against him, and my pussy gets all hot and wet, and then we usually have some great sex. I think I'm gonna surprise him on our wedding night and let him bareback me. I haven't told him, but I have been getting off while imagining him pounding his cock deep into my asshole. I can give myself more than one orgasm at once, just thinking about that big dick inside my ass.
166. Man's Story: Anal Intermission
I went to the movies with a friend and my new girlfriend. We kept kissing during the film and finally we had to go outside because it was disturbing people. I took her to the men's room and it was empty. We went in a stall and locked the door. I took charge and ripped off her clothes. Without foreplay she put a finger in her mouth and slid it into her ass. I always wanted to fuck a girl in the ass, and now it was happening. I pushed her against the wall and forced her ass in the air, then did what she had done to my own cock to make it wet and slidy. I pushed a finger in first as I wanked my cock to get more juice from the tip of it. I managed to get her ass to grip my finger and said, "Do that to my cock and I will give you your cum like a good girl." She moaned in anticipation, and I held her hair tightly with one hand, guiding my cock into her young firm asshole at the same time.
It took a moment to slide in and for her to get over the pain, then I spat on my cock some more and pulled her hair. She knew she couldn't scream because there were a few men in the bathroom by now, talking. I slid hard into her teeny asshole and pulled her hair towards me. It took a few strokes, then I knew I had to cum in her, so for the next 30 seconds, as the men talked and pissed outside, I silently ass fucked my baby as hard and fast as I fucking well could, imagining it was her punishment for being a bad girl. As I came inside her it was the warmest most amazing thing ever. I pumped hard and grabbed her hips to pull them close into me as I fucked her and came deep. I bit her as I jammed into her one last time. We kissed deeply after and she was shaking.
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