Tiffany stays in the city

Ever since I was a teenager I had been fasinated by the thought and feel of dressing up in womens clothes. The thrill and exitement of possibly getting caught in the act, and the fantasy of what the consequences might bring. I loved to entertain the thought of being sprung all dressed up like a sexy slutty girl and then being made to perform sexual favours for my discoverer so as he would keep my secret. Like all young crossdressers the thought of being forced to kneel at the feet of a horny well hung guy and be made to take his hot hard cock between your glossy red lips and swallow his manhood into your mouth and throat until delivers you his salty reward is a fantasy that can never seem to come true fast enough.

I had been talking to David for a while now, each letter and phone call seemed to be getting raunchier and raunchier...we had to meet. He was always a little coy about his personal details, I knew he was married and a successful businessman. I could tell from his voice he was a strong dominate man, which appealled to me. David had arranged to meet me in the lobby of one of the cities upmarket hotels. "Wow" I thought, as I mingled around waiting for his arrival. I had arrived dressed in my man clothes, unfortunately I didn't have the confidence or quite the right feminine styling to be passable out in public places. I had packed myself an overnight bag containing Tiffany's things which was drapped over my shoulder. I had been there for quite a while by now, wondering if this was a mistake. Would he even show up? Has he already seem me and not liked what he saw? Thoughts were constantly racing through my head. I was daydreaming about the luxury hotel suites upstairs, thinking this was a fantasy come true. My mind was miles away when a charming older man in his 50's put his hand on my shoulder and whispered "hello". "David?" I asked. "Yes" he answered, "follow me", he said as he made his way down the corridors. We went left, we went right, up, down, I was getting lost. Finally we exited through a doorway into the carpark. I was getting a little confused. "Hop in", he said. "Where are we going?" I asked with a puzzled look. He explained that he was staying in a motel on the outskirts of the city, and had only asked me to meet him here because it was nice and public. He opened the door and gently ushered me into his car. My mind was starting to think worrying thoughts, I am getting into a car with a total stranger not knowing were we are going or what he will do to me, was this even really the David I had been speaking to? He hopped into the drivers seat and placed his hand on my knee, "Don't worry, it is only a short drive and then you will have time to get changed and have some fun". We made a little small talk as we drove through the traffic, before I new it we were pulling into a motel carpark. I grabbed my bag and walked up the stairs and down the long corridor, David walked behind me with his hand on my shoulder. "Here we are", he said, "You can get changed in there if you like, I will make us some drinks", he said.

I went into the bedroom, taking my time to make myself as feminine as I could. I laid out the clothes I had chosen onto the bed, a sexy black bra, panties and suspender stockings, my favourite sleek little red dress which hugged my curvy athletic body and a pair of sexy ankle boots which made me look just that little bit slutty. I looked at myself in the mirror, my dress sat nicely, hugging my perfect round ass and my long silky legs looked amazingly sexy. I continued to get myself ready, fixing some false nails to my fingertips, putting on some makeup and some nice bright lip gloss and fixing up my wig. It was the first time I had worn a wig and I was suprised at what I saw when I looked into the mirror. It made everything come together perfectly. I could feel myself getting aroused, hopefully David would like what he saw also. I put on some jewelery as the finishing touches and I was ready to go back out into the lounge area to give David a bit of a fashion parade. I was feeling a bit nervous. I took a deep breath and about to open the door when I paused for a second. I could hear voices coming from the next room, there was somebody else in the room talking to David. I couldn't make out what they were saying but I could hear laughter. I listened carefully at the door, I was sure I could only hear two men. What was going on I thought to myself?

"How are you going in there Tiffany?" David asked from the lounge room, "I have someone else here I would like you to meet." I thought to myself that this night had not gone at all how I had planned or imagined. I hardly knew David, I mean he seemed like a nice guy, but I had never meet him before tonight and who was this other man, and why hadn't David mentioned him before. I nervously opened the door to see the two men sitting laughing together on the couch drinking some wine. The other man was a similar age to David, about mid 50s and quite handsome, he had a stocky build but not overweight. "Well hello there," the other man said, "I say, you are a pretty little thing aren't you, David warned me you were a bit of a stunner, My name is Richard." He stood up to greet me, taking my hand and giving me a little peck on the cheek. "Thank you", I said, "Nice to meet you too." I walked over to where David was sitting and he stood up, smiled and gave me a nice lush kiss on the lips. "Wow, I must say you do look special don't you, I hope you don't mind if Richard joins us tonight also". I looked back at Richard, he was very handsome and smooth talking. He had almost instantly put any fears I may have had initially to rest. "Of course not", I replied with a cheeky smile. Richard poured me a drink of wine and I nuzzled into the couch between these two handsome gentlemen. I felt instantly at ease the these two men, we drank wine, laughed and made small talk. I was feeling totally in character with how I was dressed, a sexy young girl. Soon the conversation started to get a bit more risque, both men started to rub their hands up my legs and up under my dress, Richard was nuzzling my neck and nibbling on my ear, it was making me all hot with goosebumps. I placed my hands on the two mens crotches, I could feel that they were both getting quite erect at this stage. One by one I loosened off each mans trousers exposing two quite thick semi-erect cocks. "Mmmm", I moaned to myself as I worked both my hands up and down on these two beautiful cocks. David lent over to me and gave me a long passionate kiss, as Richard continued to caress my legs and bottom. As David and my lips parted from our passionate enbrace I looked down into David's lap, seeing his nice semi-hard cock poking up at me. I smiled and looked back up at David and he gently put his hand on the back of my head and guided my mouth onto his already hard cock. My lips parted, engulfing the knob of his quite thick cock. My lips and tongue traced up and down the length of his manhood, slowly working it in and out of my mouth taking more and more of his length each time. Soon he was fully hard and I had managed to englulf his entire length. I could feel my nose and chin pressing hard against his crotch and thigh as his thick cock filled the width of my throat. I continued sucking up and down on his beautiful cock, exploring every bump and vein along his length. As I took his cock deep in my mouth and throat again I felt a firm hand on the back of my head pushing me further onto his cock and holding me there. I tried to stay relaxed, but my mind was starting to panic from lack of air, as he continued to hold me hard against his lap thrusting deep into my throat. Finally his hold loosened and I was able to gasp some welcome air. "You know Richard, this slut realy knows how treat a cock. Tiffany, how about you show Richard what a good girl you are." As I had turned to see Richard, he had already removed the rest of his trousers and had positioned himself on the couch, laying back giving me easy access to his raging hardon and hairless balls. I worked my way over to him, nestling in between his legs instantly taking the whole of his length to the hilt. "Wholly dooly!" he exclaimed as he watched his cock disappear deep into my mouth and throat time and time again. Both men were very similar in size, around eight inches and both quite thick, very much quite a mouthful. This felt amazing, very natural indeed, I felt totally feminine sucking on these two beautiful cocks.

I could feel some movement behind me, and soon felt Davids hands gently pushing my dress up over my bottom exposing my silk panties. I felt a slight tug as he guided my underwear off of my bottom and down my legs and onto the floor, leaving my bottom exposed and slightly cold. He squeezed my cheeks and gently cupped my balls giving them a gentle massage. He started to kiss my lower back and a could feel his tongue tracing my exposed man pussy. "Oh my god", I tried to say with a mouth full of cock, I jumped a little as David tongue darted in and out and across my hole. I could have almost came there and then, such was my state of arrousal. I finally composed myself from the initial shock of Davids's tongue in my ass, relaxed and warmed to the unexpected feeling of sensitivity that my man pussy was giving me. David's tongue darted in and out of me making me moan as I continued to suck on Richard's enraged manhood. My moans were starting to affect him also, as the gentle vibrations from my moans stimulated him even more. I could feel his cock harden a little bit more as he placed his hands on my heads pulling me onto his cock a little bit harder and deeper than before. I felt a cold sensation on my bottom as David poured some cool lubricant over my ass, slowly I felt a small pressure at my entrance as one of his fingers started probing my pussy, first one then two fingers as my muscles relaxed and my ass was nice and ready. Next I felt a hand on my hip and some pressure at my entrance as David rested his knob against me and slowly pushed, there was a little pop as my bottom accepted his quite large knob making me gasp. A warm pain engulfed me as my bottom adjusted to his size and I started to relax a little. Sensing I was ready, he grabbed my hips firmly and gently pushed his big cock inside me in one long slow movement until his balls rested against mine. Then slowly he began rocking back and forward, slowly thrusting his cock deep inside me. I let out a deep moan as he slowly started fucking me, his grip on my hips tightened as his thrusts became harder, deeper and more intense. Every time he would drive his cock into me he would push mouth further onto Richard's cock. I was being filled to the maximum at both ends. What a slut you are Tiffany, I was thinking to myself, so glad that I hadn't chickened out with all of my original doubts. By now David was getting very vocal, calling me a dirty little whore and really giving my arse a good pounding. He was fucking me like crazy for what seemed like an eternity, I could feel him getter harder and harder but he just kept going, grabbing my hips and slamming his cock into me. Finally he gave out a huge holler as his body went all stiff and he shot his hot sticky load deep up me. His thrusting eased off as he gently massaged his softening cock in and out of my bottom. He sat his spent body down on the couch next to me with the hughest smile on his face, I looked at him and smiled, then slowly lowered my mouth to meet his softening cock, gently sucking it and soothing it with my lips slowly sucking the remaining cum from his spent cock. At this time Richard had positioned himself behind me and in one uninterupted movement plunged his cock to the hilt up my now supersticky bottom. Richard was more gentle on me than David was, with nice long, slow, deep thrusts. He must have been hitting the right spot because it was feeling amazing, I could feel my bottom quivering on the verve of climaxing. He was keeping me on the edge of cumming. It wasn't long before his thrusts started to get quicker and more intense, I had a feeling he wouldn't last as long as David had, especially since I had been sucking his cock for almost an hour. He reached his hand down to grasp my now rock hard cock, it only took a couple of touches and my body couldn't take it anymore. My arse muscles clenched tight around Richards cock as I spurted my cum into his large hand. This must have pushed him over the edge because he pushed me hard into the couch, as last few furious thrust nearly split me in two before he too shot his hot sticky load up me, before collasping onto my back, still buried deep inside me. He slowly eased his cock out of my bottom as he slowly softened. He lent around to whisper thank you in my ear. I turned my head toward him and smiled, "No, Thank you", I said. He lent forward further and gave me a nice long passionate kiss.

We all got up to straighten ourselves out, David had already got up to shower earlier and was walking around in his bathrobe. Richard and I went into the bathroom to have a shower and wash off some of the sex that was starting to run down my leg. We hopped into the shower, Richard soaped up my back and began massaging my shoulders and down my back, having a playful squeeze of my bottom and legs as he went. I turned around and let him rub my chest, tummy and hips. As his hands got down to my waist he lent forward and gave me a long passionate kiss, his tongue darted in and out of my mouth as he pulled me close to his hairy, stocky frame. It was one of those kisses that makes you go week at the knees, very tender. I could feel his manhood starting to swell and begin rising to attention once more. I slowly guided my way down his body and on to my knees, the warm water from the shower was keeping my back and neck warm, I reached forward with my lips and drew his hardening cock into my warm mouth, Richard let out a low moan as I began once more to take his manhood between my lips.....