• ← Older Blog
• Newer Blog →

True ANAL Sex Stories

By Escort-List World Wide Escorts Directory, 4th October, 2015

Man's Story

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.

 

Woman's Story

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.

 

Man's Story: Ass Passion 

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.

 

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. 

 

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.

 

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.

My boyfriend and I were out one evening having a few drinks and he told me he had a surprise for me. We left the bar and he took me to the beach. As we walked around the beach, things started to heat up as we were touching and deeply kissing each other everywhere! He took me by the hand and walked me to this beautiful old lighthouse we had seen many times during our visits here. He looked at me and asked if I wanted to go in. I was eager to explore all of him and the lighthouse, but was afraid we would get caught. He said that was part of the thrill and he wanted to show me the thrill of trying new things.

We climbed in through an open window and walked to the top. The view was beautiful as we stood leaning against the rail. His hands reached around me from behind and started to massage my tits as he kissed and sucked on my neck. I leaned back into him and felt the pressure of his cock against my ass so I started grinding my ass against him and he began to moan. (Actually, it was more of a growl.) It was at this point that he whispered in my ear, "Do you want to experience the thrill of something new?" I knew I was ready. I wanted so much to feel his hot throbbing cock in me...all of me. I wanted to give him my ass. I told him to fuck me!

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.

We are still together and anal sex has become a regular part of our sex life. It is one of the most erotic things we do because we always remember the first time and the power of living for the thrill.

 

 

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.

 

 

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.

 

Surprise development

At first anal sex was a definite no with my wife. She made it quite clear from the start and I never bothered raising the issue. One night during some play she was laying on her front as I was fingering her pussy and I leant forward, parted her legs and licked her anus; it just seemed like the right thing to do at the time. As I did this I thought she would either be turned off or make a comment about 'not going there' but instead she responded by pulling herself up on to her knees and bending right over, I licked her anus more and used plenty of saliva as I started to push my tongue further in to her.

After doing this for around 5 mins I took some of the lube I had been using on her pussy and gently rubbed it on to and around her anus, I used plenty of it and slowly and very very gently passed my fingers around her anus sliding them around in the lube and she asked me to carry on in a very turned on and sexy voice. After a while I took a beep breath and really gently started to put ONE finger in her anus, I was waiting for the 'dont do that' but all she did was move herself nearer me and pushing my finger farther inside, I was surprised to say the least but carried on with this, then with more lube and again very slowly I pushed two fingers in.

She started to move herself forward and back on my fingers so I moved them in and out as if I were fucking her, at this point she became super aroused and was moving faster banging her cheeks on my hand, I used my other hand to rub and finger her pussy and she just went wild, pulling at the bed sheets and shouting 'yes yes' and I can't tell you how amazed I was, this continued until she had an orgasm and laid back on the bed, she was bright red with panting, about 2 mins later she was asleep.

The next time we had sex I did the same as before except this time I took the courage to penetrate her and one thing that made her scream 'fuck me fuck me' was having my dick in her ass and my fingers in her pussy, I came so hard in her anus that I was out cold in no time. On the third occasion we had the usual foreplay, some pussy and anal fingering then she broke her own second rule. She gives a great blowjob no problem but I never ever came while she did it. This time she sucked me until I could not hold on any longer and I told her I was going to cum but she just kept sucking until she had the whole lot in her mouth. I have no idea why things suddenly changed like this but let me tell you I ain't complaining.

 

Winning her over- Jess, Age 25

I used to be disgusted about the thought of having anything around let alone in my anus. However, one night my husband gently rub by rosebud while giving me oral sex. I just about went through the roof. It felt so good. Then he asked me if I wanted to try anal sex and I said yes. He made sure that he was really lubed up (we find astroglide works best as it stays slippery without drying). I had my first true orgasm that night. It was incredible. The key was lots of lube, going slow and communication.

 

Careful research

I've recently had my first anal sex experience with my long term partner. It's been my fantasy for many years, but I've had medical problems which required surgery in my anus. I've since been too scared to try anything back there.

After my partner mentioned he'd like to try anal sex, I came clean and said I would too, but was scared of ending up back in hospital due to injury. We set about buying toys & lube and did some research. We had a couple of goes, but were disappointed after I chickened out, but I didn't want to give up. My boyfriend said not to try again if I found it too uncomfortable, and I appreciated the pressure being taken off. I found this site and must have read every single story for tips!

We were having sex, and I knew I was ready to try again. The best tip I got was to have him penetrate a bit, wait and relax, then a bit more etc... Deep breathing was also very helpful. He followed my every instruction, and I think a respectful partner is paramount here.

I was amazed it wasn't painful, and there was no blood, which I expected after my previous problems. I had the most intense orgasm, and so did he. He said "you've never made a noise like that before"! In fact, I think I'm a lot more keen on it than he is!
I think anal sex will feature regularly in our future sex life. Thanks to everyone for posting their tips and helping us out!

 

With the Ex 

The first time I got anal was when I was married to my otherwise frigid ex-wife, Heather. We were uncharacteristically naked and messing around one warm, lazy Saturday afternoon when I dared to act on a longtime fantasy of mine and started to gently finger her anus while I ate her pussy. She started to respond to my gentle probing much to my surprise and I got a little more aggressive. However, I didn't get my hopes up until she suggested I get some lube. I wasted no time in sprinting for the bathroom where I grabbed some Vaseline - the only lube we had. I leered to myself in the mirror and shot
myself a wink before running back to the bedroom. Imagine my surprise when I found her face down on the bed, her fat ass already in the air. My dream come true! I quickly knelt between her thighs, generously lubed up my engorged prick and her tight asshole and started to ease it in as best I could - I was so hot I was ready to explode. She then said that I shouldn't come in her ass but should pull out instead. "No problem", I said. I didn't mean it but what the hell.

She moaned in pain as I slowly pushed my cock deeper into her and she begged me to finger her clit, but it was out of my reach, so she frantically fingered herself instead. I finally got my thick six and a half inches of meat in her behind and I rested a minute so I could enjoy this ass-fucking as long as possible; I knew it was probably the first and last time she would ever let me enjoy such a delicacy again. I finally responded to her pleas to hurry up and I started to slowly stroke my cock in and out of her. I reveled in the new sensations of her tight virgin ass wrapped around my cock, her sphincter drum-tight, and how good her fat ass felt against my belly, as I ignored her earlier request and proceeded to have the orgasm of my life when I unloaded a tidal wave of semen into her rectum. I did pull out and gave her butt a final courtesy squirt of come, just to show her I did listen to her.

Afterward, as she sat on the toilet, she bitched to me how that was fucking and not making love and I had to agree with her for the first time in our marriage!!!

 

An older married man

The first guy to do me anally was an older married guy I played with for a while. His wife wouldn't ever do anal for him and he practically begged me to let him in my ass. I hadn't before (I was only 18 then) but I was ready to try it. He was so sweet about it, going slow, making sure it was alright. Which was good right at the beginning, but after a couple minutes of that, I was like "quit being so nice and just fuck my ass". And he did and it was great. He had the most intense orgasm I've ever felt a man have. Lot of years of built-up anal frustration came out in my butt I think. I got off so much knowing what it meant to him to finally do something he wanted to so badly.

 

 

 

Related Blog Posts

• Types of Clients – (An Escort’s Perspective)
• We have the most open minded escorts girls in London
• Interview with Party Escort Reina
• Pegging and Strap-On Escorts A Beginners Guide
• ANAL PLUG. Diana's Bunny Tail Butt Plug for Halloween