My Anal Wife and Girlfriends

I was felling pretty pleased she had got off, and she offered o give me a hand job by way of relief, I declined but asked id she would show me her arse while I finished my self off. She was a sport and did a little strip, rolling her skirt down and fondling her arse for me, then she leant forward on her knees, resting her elbows on the sofa, and pulled her cheeks apart a little. Well that was more than I expected, I shot my load in my hand, the sight of her luscious bum framed by those suspenders, and with her cheeks pulled slightly apart I could see a semi circle of the brown pucker of her anus each side of the thong, and her soaking crouch, covering what felt like a very nice little cunt.

We settled down then, and talked all night, we really hit it off, and we made a date for the next evening.

The next evening came and I went to her place. She was looking good, and we kissed as soon as I got in the flat. We carried on without any delay and pretty soon we were down to our underwear, she looked good, she still had a bit of a tummy and she was a bit self-conscious about it, we got on the bed and played for some time, she asked me if I wanted a blowjob, “well if you don’t mind” as long as we do a 69, which gave me a great look at that luscious arse of hers. She still had her suspenders on and no knickers or bra. I began to eat her gorgeous pussy as she sucked my cock, to be honest I’ve had better head, Donna gave great head, but it was our firs time, and the view of her arse made up for any oral deficit. Suddenly she took it up a notch, and the sucking was quite superb. Keith obviously trained her well.

There was some humour too I begged her not to fart with my nose practically wedged in her arsehole. At this point I noticed her anus looked like it had been fucked before? I suppose I shouldn't have been surprised, Keith had been fucking her for years, only make sense he must been slipping it up her bum from time to time.

Going back a few years for bit, I have only deflowered one girl’s bottom, my first proper girlfriend Haley when we were both 17, and not very well I might add. We only did anal a few times, and she really hated it. Of course she was very tight, and I was not skilled enough to make it pleasant. I suspected I had put her off anal for life, but she dated a friend of mine Spence and he told me when she was drunk one time that she had let him fuck her in the arse! She told him he was the first (I’ve noticed over the years this often happens)? He was really fishing to find out if I we had done it, and I told him with some glee that I had been up her bum at least six times when we were dating. He seemed a little put out by this information. I don't know if this news had any impact on the relationship but they did split up soon afterwards.

Haley confronted me after the split, asking me if I had said anything to him? I denied it blaming her girlfriend, who I know she had told about me popping her anal cherry, as she had given me a hard time about it (Girls who took it in the arse were pretty rare in the 80’s in the UK, at least round where I lived). For a girl who hated anal Haley let practically every one she slept with do her in the arse, in fact she something or a reputation for in our circle for taking it in the bum, so she must have developed a taste for it? Eventually she shacked up with a much older guy and had a couple of kids.

Joanne was an anal virgin (no doubt about it, anus as tight as a button) and despite have fucked quite few guys was determined to remain so, as were all the other English chicks I have slept with.
Anne and I moved on from oral to some missionary fucking. As I penetrated her for the first time she was a little vocal, she said “go slowly as I haven’t done it for a while”, but as I said she was a bit self-conscious about her tummy, and after a short while she asked me if I would like her to turn over? I said sure if that’s what you like, she rolled over onto her tummy. I straddled her and carefully aimed for her cunt, sliding up her with ease. Everything seemed to line up better in this position her pussy was quite near the back. I started to thrust into her watching her arse cheeks squish against my groin with each stroke, I could get in deeper like this as one usually can from behind. She coaxed me on telling me to pull it out slowly, as far as I could. Now I’m not that long but I have a good girth, and I didn’t want to slip out and accidently (no honestly!) push it up her bum, know girl really falls for that “woops wrong hole” line. I put my hand over her anus to guide me back into her pussy, as I was withdrawing completely with each stoke now.

I felt like a change of position so I made the first request of the evening, “can we do doggy?” she stuck her bum up in the air without a word, one obedient girl! And I started really fucking her hard like she requested, she seemed to be loving it, and again that gorgeous are rump was slapping against my groin as I drilled her cunt like a dog. I started to talk to her.
“You like me banging your pussy don’t you?”
“Yes I like it”
“You like it like a little doggy don’t you Anne?”
“I like it getting fucked from behind, like a dog”
“How many men have fucked you like a dog Anne?”
“Not many I’m a good girl?”
“Your not a good girl, If I asked you to bend over the bed head I bet you would?”
With that she quickly got up and bent over her bed Head as I asked. I asked her.
“Would you like me to get behind you and give a good seeing to from behind?”
“Yes do it, fuck me from behind!”

I slammed her from behind as she wanted, we finished of the session with her on her tummy, which is one of her favourite positions.
The next few dates progressed well, lots more get too know you, and lots of fucking pretty soon it was a month latter and I was up for another trip away. I didn’t want to go. Anne was already back at work and I knew she had dated some guy in London over the last few months, so I wasn’t over the moon about leaving her at this point but I had too go the states again, for a couple of weeks.

After shagging a lot over the last few weeks or so I started playing with her anus while we were fucking, she didn't complain, soon I started to slipped a finger up her botty while we were fucking. Well she could have slapped face and dumped me, which is always a risk, but in conversation she had alluded several times to anal sex, and we had watched porno's with girls getting drilled up their bums, to which she commented "I don't know how they can take up the bum like that!" The implication was I thought, she knew how she liked it up the bum? I had told her my war stories and she knew I was a kinky bugger. But she never outright said told me she took it in the arse.

One time I was in her flat looking through a draw for something when I found a tube of AnalEaze almost completely used! I so Keith must have used up on her bum? Unlike Spence It has never bothered me what my girlfriends had done with other guys, (well as long as she let me do it too!) She also had some porno mags, one title Derriere is all anal with nice looking girls with reamed out bottoms. Don't get me wrong Anne wasn't reamed out like the girls in the mag, she was a nice girl with a nice little anus, it just looks like its been fucked a few times.

I wanked thinking about her arse when I was in the US on business the next week. One time we were having phone sex I actually got her to finger her arse for me! She promised me anal when I got back, so I went to the local sex shop and bought a few toys. She said she wanted to try a vibrator, and I got a couple one bigger for her pussy and a slim one for her bum. I also bought a pot of anal lube, as they were out of AnalEaze, the crazy looking goth woman in the shop told me it was the best, presumably she knew first hand? I had to pack them in my case and hope it wasn’t opened by customs on my return to the UK.
When I got home she was looking sexy, she had lost a few extra pounds in my absence and she was wearing a little red skirt suit she had worn to work that day. Don't get me wrong she wasn't fat, but the extra few pounds really bought out her figure. We hadn't said we were exclusive yet, and I had a dalliance with my American ex Donna. She had just split up with suit guy who she left me for.

I was a bit jealous when Anne told me on the phone she had dated some guy she knew who was a client of the firm she worked for a few times, as we talked I got turned on as she told me how he wanted to fuck her, but she made him wait until the third date. I was a bit green now I didn’t like the thought of her bending over for someone else, but at the same time it turned me on.

I arrived back at her flat we shared now. As soon as the door opened the atmosphere was palpable, we started kissing and feeling each other up, she had suspenders on and a thong under her skirt, and I copped a good feel of her backside gently finding my way to her wet cunt! I asked her if she was thinking about him, she replied “no he wasn’t as good as you!” (That’s a confidence booster) I slipped a finger into her wet pussy and asked her “If she liked his cock up her?” She was leaning forward against the sofa now wiggling her bum as I explored her moist vagina and clitoris. I wriggled my thumb up her crack until I found her anus, she let out a small gasp! I asked her “did he do you from behind?” she replied “what do you think?” She did love it from behind. We continued kissing and I was now in my position behind her kissing her neck with a hard on like milk bottle. I pushed my thumb into her anus about an inch. She wiggled her arse with approval, the only lube I had on it was pussy juice and I didn’t want to make her sore.