Written by MrsBridges

18 Aug 2010

Hello, This is a story about what me and my ex did. Yes it’s long - pity he wasn’t - but I enjoyed the encounter and wanted a way of remembering it.

Thomas approached me in a chatroom offering to clean my shoes whilst he was dressed as a maid. I was a little shocked at first but went along with the role playing chat. Little did he know until we actually met, that I own over 150 pairs of shoes so he was going to be a very busy submissive maid!

Thomas was perfect for me as he lived in a Scotland, me England and there was no chance of him popping round to mine whenever he felt like it as I liked my space and he liked his.

I’m not into men dressing as women as I personally feel that unless they can carry it off convincingly, and most on here cannot I’m afraid, then in my opinion they just look ridiculous. I’d also never thought that I would be turned on by a man wearing stockings and suspenders but that was until I found out that an ex of mine was into wearing them.

Thomas liked to wear lingerie when wanking on cam in the chatrooms and

I found it very horny watching him as he stroked his small cock whilst he wore stockings and suspenders.

Our first meeting was in a hotel and I was hungry so sent him out for a KFC and got myself ready for his return. I wore a tight fitting basque that showed off my ample bosom, sheer black stockings, panties and black stiletto heels. I lay back on the bed waiting for him to return and he told me that when he got back he didn’t think I would still be there so was excited that I was.

As he put the bucket of chicken down, I pulled him towards me and started to kiss him passionately for some time until I moved down his body, unzipped him and started sucking on his already erect cock. He told me he wanted to be dressed in lingerie when we had sex so reluctantly pulled his swollen cock out of my eager mouth and went into the bathroom to get changed.

He came out dressed in a basque, stockings and suspenders and I could feel my clit tingle and my panties get wet as I looked at him. He climbed onto the bed and started to kiss me again but for some reason he couldn’t get hard! We decided to watch TV and eat the chicken, hoping that this would make us feel more relaxed. As we talked we both mentioned what we did and didn’t like sexually. Eventually we went to sleep without having sex but we’d had a great time despite this.

I woke up first and remembered something Thomas had said he liked being done to him so I decided to wake him up by burrowing under the covers and taking his cock in my mouth. He told me afterwards that what was most thrilling about this was the way I just held his cock in my mouth first, letting it start to stiffen in the moist warmth. Then as it filled me I began to take long deep sucks on it, using my tongue around his head to lap up his pre cum. When he was nice and hard I climbed on top of his stiff cock.

“Tell me what you want me to do.” I said as we rocked in the missionary position, he told me he wanted my finger in his arse. I put my hand between us and got my finger wet from my juices, then I inserted my middle finger deep into his arse. I was immediately rewarded as he began thrusting harder, faster and deeper. As hard as he thrust forward into my pussy, he pushed back onto my finger. After a time, I began inserting my index finger alongside the first. He started making animal noises as the pressure in his rectum and against his prostate began an ejaculation like no other he had experienced. His ecstasy triggered mine and we shared explosive orgasms.

That night launched adventures in anal sexuality that I dream about. After we recovered from our first orgasm, he moved down my body, kissing and licking. He wanted to focus instead on my anus. He hooked my legs on his shoulders, widened my crack and inserted his tongue into my arsehole. My reaction was immediate and wildly enthusiastic: “Yes, yes! Deeper!!! Yes!!!” his depleted cock stood up in no time. When I was sufficiently aroused, he straddled me and inserted his cock in my now fully lubricated arse. From then on, I guess he came in my arse about as often as in he came in my pussy.

For my part, I showed up at one of our meets with a present for both of us – a strap on cock. I could tell from his immediate and intense responsiveness to my anal ministrations that Thomas was a man who would enjoy being fucked on his back, legs in the air with an eight inch black cock in his arse.

As it was, I could clearly understand how much I enjoyed this aspect of our sexuality and he seemed to enjoy it too, since whenever I wore it his cock was perpetually hard. We had no inhibitions about discussing our sexual history and experiences. When the subject of group sex and swinging came up I admitted to him that the closest I had come to group sex was having sex with a boyfriend in a room with another couple. They were screwing as well and we watched each other fuck then I enjoyed the cocks of both men.

I told him with great pleasure how much I got off on kneeling before them, taking one, then the other, and finally both cocks in my mouth at the same time. Thomas asked if my partners seemed uncomfortable having their erect cocks in contact with each other. I assured him that they seemed to enjoy it so much that I would make a point of rubbing them together. The highlight of that night was my first double penetration. I looked at Thomas meaningfully and told him I wanted to experience that with him. He was happy to oblige and admitted that the idea of a threesome with me, him and another man would be extremely horny.

Thomas thought we should advertise for a third but I was wary of doing this and told him we should go with a known commodity, known to me that is.

I knew Rob before I met Thomas and we’d had some horny fun together. Rob had told me he enjoyed sucking cock and fucking other men in the arse.

Thomas came down from Scotland and I introduced him to Rob at the bar we’d arranged to meet at. I had thoroughly briefed Rob on the plan for the evening and our conversation at the bar, lubricated by several rounds of drinks to overcome inhibitions became ever more sexual. I know that I was getting aroused and judging by the flush on Thomas’ cheeks, he was as well. Rob talked about being picked up hitch-hiking by a gay photographer and his seduction. It turns out that somewhere in the world of porn are a number of photographs of a younger Rob sucking on the cock of his patron.

That anecdote seemed to signal that the time was right to head back to our hotel. We were oddly silent on the ride up to the room, each of us probably wondering exactly how this encounter would play out. I opened the door, stepped in, turned on the light and invited them to begin having sex with me once they were dressed in stockings and suspenders, so they went to the bathroom to get changed. When they emerged, Rob didn’t hesitate in starting to kiss me passionately. At first Thomas was simply a spectator, stroking his small cock and somewhat at a loss, but in a moment he saw an opportunity as Rob began kissing my neck. Rob replaced his lips on me and could sense in my kiss the intensity of my excitement. While our tongues caressed each other, Rob began stripping me, unbuttoning my blouse, opening my skirt, and exploring my body.

Rob and Thomas each sucked on one of my huge lush nipples, their hands encountered each other at my pussy and at the crack between the ample cheeks of my sexy arse. Bit by bit, without speaking, Rob and Thomas figured out how to share the erotic territory of my body with a degree of grace. One would stand and adore my breasts and nipples and one would kneel and worship my labia, clitoris and anus. They switched positions once and then I asserted myself.

I pulled Rob from between my legs and the three of us stood briefly kissing and embracing. I was mildly surprised to realize that Thomas was kissing Rob as well as me and that his tongue was in his mouth from time to time. The novelty and taboo nature of all of this had their cocks as hard as iron. I was in a haze of sexual excitement. Thomas found my right hand exploring Rob’s bottom as his left explored mine. I broke off from kissing them to slide to my knees. I took Thomas’ painfully erect cock into my mouth first. While I sucked his cock, Rob began tweaking his nipples and sucking on them. He moaned with pleasure. Suddenly, he found a stiff 8 inch cock in his hand and experienced a surprising thrill. He had never touched another man’s cock and couldn’t believe the excitement he felt. Nothing could have prepared either of us for what happened next. Rob slid to his knees and started tonguing my arse as I continued swallowing Thomas’ cock. As I felt Rob’s tongue penetrate my arse Thomas thrust his cock down my throat. I was in Heaven! All of this was a prelude to the ultimate point of the evening.

I found myself so excited that when I rose and moved towards the bed, Thomas said he was ready to do anything to continue this degree of excitement.

In bed, I first arranged Rob and Thomas so that I could easily alternate sucking their cocks. Before long Thomas sat up and I directed him to kneel over Rob and take his cock in his mouth. He said the pressure was gentle, but determined. He hesitated a moment but was actually excited at the prospect. It was a handsome cock, smooth and very hard.

Thomas leaned forward, opened his mouth, and welcomed Rob’s cock by swallowing as much as he could. I made approving noises and occasionally would kiss Rob deeply. Thomas became intensely absorbed in Rob’s cock. Rob and I were very absorbed in each others mouth and nipples. I made several comments about what a good bottom Thomas was going to be and that after tonight he may give up pussy for good.

After some minor changes in position, we were ready for the main event.

I arranged myself in the missionary position and urged Thomas to mount me. He was a bit surprised that we weren’t immediately going to do DP, and then realized what Rob and I had obviously planned in advance. Thomas was so hard and excited; he had no choice but to thrust his aching cock deep into my totally lubricated pussy. Next Rob’s fingers penetrated Thomas with a load of Vaseline. After working his load of lube in, Rob inserted a second and then a third finger. In spite of his experience with anal penetration, three fingers penetrating his arse so quickly caused him to gasp. It seems he knew what he was doing though as Thomas never lost his hard on and pumped my pussy energetically.

As his arse got accustomed to being stretched by Rob’s fingers, he began responding as he did to my strapon by pushing back to increase penetration. As he began easily thrusting against the fingers, Rob withdrew them slowly. Thomas felt Rob’s hands on his hips and realized that Rob was preparing to mount him. As the head of his cock began pressing against his sphincter, he almost passed out from excitement. Since he was well prepped, his cock was quickly buried in his rectum. He moaned like a bitch as I held him and Rob began fucking him. After Thomas’ initial surrender to anal penetration, his own cock asserted itself and the three of us established a mutually pleasing rhythm. We fucked like this for a long, long time.

I loved the feeling of Thomas’cock in my hot pussy and he loved the hard cock in his arse. As I played with Thomas’nipples he would start thrusting reflexively. We went back and forth, changing tempo, touching each other in the most sensitive places. I felt like I could do it forever. Finally, Rob brought things to a wild conclusion. He began spanking Thomas’cheeks sharply. In seconds,the blood flow to his arse energized and excited Thomas to such an extent that he began pounding my pussy wildly. Rob’s grip on his hips tightened and his cock pumped his arse powerfully. As he started to come, his sphincter tightened around Rob’s cock convulsively and his thrusts quickened. I started screaming, Thomas started screaming and Rob simply yelled. I don’t know who came first, but it was certainly a three-way come. We screamed, we swore, we collapsed. We were covered in each other’s sweat, panting, sighing, exhausted.

After a few minutes, Thomas’ diminishing cock slipped out of my pussy as I gave it a last squeeze. He continued to massage Rob’s cock with squeezes of his sphincter until at last it popped out. Thomas could feel his semen trickling between his arse cheeks and felt incredibly satisfied. We were exhausted. The three of us spooned, me in front of Thomas, Rob behind and before long we fell soundly asleep.

The sky was just beginning to show some light when Thomas was awakened by the insistent pressure of an erect cock between his arse cheeks. He moaned a bit, but Rob shushed him with a hand to his mouth. He wanted this to be just boys play while I slept.

His cock slipped into his stretched and swollen anus easily, lubricated by the remains of Vaseline and a huge load of semen. They lay on their sides, still spooning while Rob gently fucked Thomas. Before long, my eyes shot open. “So you two are having sex without me!” “Well, you’re the one who taught me to love a stiff cock in their arse,” Thomas retorted. I laughed. “No, really, it really turns me on to see you getting fucked. I just need to get off. Here I am in bed with two virile guys and they’d rather fuck each other than fuck me.”

They decided to include me by making me place my pussy, still smelling of Thomas’semen from last night, right on his face. Rob grasped Thomas’ankles and pulled his legs toward him, exposing his now gaping arsehole to Rob's raging erection. He entered him and immediately started fucking him hard. Thomas begged for it and his moans and groans were muffled by my gaping cunt which I pressed hard into his face as I madly played with my clit. After Rob and I had each climaxed, we took turns sucking Thomas’cock, trading it between our mouths, one sucking and swallowing it while the other held the shaft and stroked it. After Thomas came in my mouth, I shared his with him in a deep, passionate kiss.

An encounter that was exciting and sexually fulfilling.