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Cindytranee meets the maintenance crew

Cindytranee gets caught crossdressing and gets fucked by three men
This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private and I really enjoyed being there. This was the first time in years that I had lived alone and I loved it. It gave me the freedom to enjoy my favorite thing, cross dressing and having sex with as many people as possible. I had settled into a routine of dressing up every night and all weekend and living as a female as much as possible. The only time I dressed as a man was when I had to be at work. I even went grocery shopping in drag since it was winter and got dark before I got home. The darkness hid my feminine attire from neighbors so I always shopped in the evening. I am somewhat passable but still got some knowing looks from some people which I found exciting.

I had developed quite a large wardrobe and a nice collection of sex toys as well. I would spend a lot of time surfing various websites looking for hookups and if I couldn’t find a date I’d break out my toys and play alone. The week this happened I had been very busy at work and gotten behind on my housekeeping. There were panties, stockings, and other items of my lingerie lying around everywhere and I had slid my box of toys under the sofa instead of putting them away in my closet as usual. I lived alone so what’s the harm? I planned on catching up that weekend but that was not soon enough. I was shocked to come home Friday evening to find that yellow hazard tape blocking the stairway that leads to the level above me which happened to be right next to my door. It was very cold and about half the stairs were covered in ice which is unusual since the stairway is covered and it had not rained.

I was even more shocked when I entered my apartment to find that some of my furniture had been moved away from the front part of the apartment and the carpet at the front had been pulled back to expose the padding underneath. The carpet was still wet and there was a fan blowing on it to dry it quicker. To my horror the sofa had been moved and my box of toys had been set on the dining room table with some lingerie that had been lying in that area. I called the office and was informed that a pipe had frozen and burst in the apartment above mine so my apartment had become partially flooded. The maintenance crew had moved my furniture and exposed the wet padding so it would dry. They would be there Monday to tack the carpet back down and finish up.

I had no choice but to hang out in my bedroom that night but the carpet was dry the next morning so I decided to move the sofa back in place so I could spend the rest of the weekend in the living room as usual. I caught up on my cleaning and by late afternoon was lounging on my sofa with my laptop and making a date for later with a female friend that I sometimes have sex with. She loves to fuck me with a strap on before switching places and getting me to fuck her in the pussy and ass. She wasn’t going to be able to make it until after 11pm though so I had some time to kill before she arrived. I cruised a few sites trying to find someone to hook up with before my date but had no luck so I had a couple of drinks and decided to play with my toys some. I had already showered and shaved, had a douche, powdered and perfumed, and dressed in a very slutty outfit so I was ready and feeling horny from my preparations and the drinks.

I put in a shemale video and lubed up my favorite dildo and was slowly and casually sliding it in and out of myself when there came a loud knock at the door followed by a mans voice shouting, “Maintenance”. My heart almost stopped! I pulled the dildo out and hit pause on the video and listened. He knocked again and shouted, “Maintenance”. I hoped that if I was quiet he would just go away and come back Monday. I sat with the remote in one hand and my dildo in the other expecting him to leave but almost died when I heard a key being inserted into the lock and someone unlocking the door. I jumped up and barely made it inside my bedroom before the door opened and the voice shouted maintenance again before shutting the door behind him.

I was in a panic and not sure what to do so I went into my walk in closet and quietly shut the door. I planned to wait until he was done and left and then go on about my business but instead I slipped and almost fell when the strap to one of my high heels came loose. I grabbed the wall to catch myself but ended up knocking over a set of golf clubs that was leaning against the wall. The clubs fell over onto a box of wine glasses also stored in there with a loud smash. I was totally freaking out! There was no way he didn’t hear that! I bit my lip and listened to see what he would do.

“Who’s there?” he said as he walked into the bedroom. “I know you’re in there. Now come out or I’ll call the police!” he said from just outside the closet door.

My heart was beating out of my chest and I almost fainted as he flung open the door to the closet. Both of us were speechless at this point. I was met by the sight of a large guy in a blue uniform holding a hammer in a defensive posture and he was met with a tranny dressed like a slut in a defensive posture!

After what seemed like an eternity he lowered the hammer and smiled. “Oh! It’s you,” he said. “I didn’t recognize you all dressed up like that. You know I thought you might be a tranny when I saw all your stuff in there yesterday.”

Still too much in shock to respond I just stood there.

“It’s cool, don’t worry, I won’t tell anyone your secret. To tell the truth I think you look hot! I’ve always had a thing for trannies. I even went to the XXX theatre over on Ponce one time with the other guys on the crew, you know, Earl and Jerome. My name’s Tom by the way. Yeah we went there one Saturday and hooked up with two trannies right there in the theatre! It was great!”

This made me feel much better and I was finally able to exhale. “Thanks, you guys sound like fun. You’ll have to introduce me some time,” I said. He was actually a nice looking white man. About 6 feet tall and a little stocky with a little bit of a beer gut. He had the first few buttons of his shirt unbuttoned and I could see that his chest was nice and hairy just the way I like them. I noticed a bit of a bulge in his pants too.

“They’re not here today but I can bring them by some time if you want. It’s just me today and I really just came by to get my fan. I need it at home. I could stay for a little while though if you need some company.”

“That would be cool, can I get you a beer?” I said

“That would be cool,” he replied

“Have a seat on the sofa in there and I’ll get you one.”

I gave him my sexiest walk as I led him into the living room then turned to go to the kitchen. I brought him his beer and sat next to him on the sofa. He noticed the paused video on the TV screen. The scene was stopped with a shemale on her knees giving a dude head.

“Looks like fun,” he said.

“It is fun,” I told him as I pressed play on the remote. The action n the screen resumed and you could hear the slurping sounds as the shemale on screen continued to suck the dude’s cock. I noticed that Tom shifted in his seat a little to reposition his growing cock. I was getting horny again too but was not sure how to proceed.

We sat watching the action on the TV until there was a break as the shemale stopped giving head and stood up to remove her bra and panties. I looked over at Tom and he looked at me and then without saying a word he leaned in and kissed me. His tongue invaded my mouth as he wrapped his arms around me and I melted into him. While our tongues danced I was extremely turned on by his rough whiskers on my soft smooth skin which is something I always love. He moved one hand to my hip and started pinching my nipples with the other as we continued making out like a couple of teenagers. His kisses were very passionate and made me want more.

I slipped off the sofa and in between his legs on my knees. I unzipped him and slid his pants and boxers down to his ankles. His cock was nice. It looked to be almost 8 inches and was uncut. I stroked it a few times pulling his foreskin back to expose his head then licked it up and down like an ice cream cone. He moaned as I took him into my mouth. I bobbed up and down on it while massaging his balls and took my time to make sure he enjoyed it. I loved the musky smell of a working man and his precum tasted very sweet. It wasn’t long before he filled my mouth with quite a load of hot sticky cum which I savored as I swallowed it down. I licked him clean and was surprised when he leaned down and kissed me afterward. I’m sure he could taste himself on me but his kiss was still very passionate and I melted into his arms again. I sat on his lap and we kissed until his cell phone rang. It was his wife and he had to go. He told me he was sorry that we didn’t have time to finish but he would make it up to me, gave me a kiss and then he left.

I had enjoyed the excitement of being caught in drag and the spontaneous hookup but was frustrated since I didn’t get to finish. I had another drink or two, ate some dinner and settled down to watch TV until my date came over later on. It was about 8 and I was just about to doze off and the doorbell rang. Wow, I thought, Linda must have gotten free early. I peered through the little hole in the door and was surprised to see Tom and the other two maintenance men, Earl and Jerome standing at my door with a case of beer and a bottle of wine. I opened the door and let them in. Tom said that they were all planning on going out together anyway so he had suggested they come over so he could finish what we had started. We opened the wine and they all grabbed a beer while I poured myself a glass then we sat on the sofa together.

We drank and chatted casually for a few minutes and Tom asked if I would put on the video we were watching earlier. It was still in the player so I pressed play on the remote and restarted the show. The attitude in the room changed almost immediately. Everyone got quiet and Tom started kissing me. His wet tongue in my mouth and his rough whiskers on my face made me melt again and I knew I was theirs to do what they wanted with me. Tom stood up and I helped him remove his pants and boxers while he took off his shirt. I cupped his balls in my hand and started deep throating his cock. He had showered by then and now his musk was mixed with the smell of body wash. Earl and Jerome alternated between watching me give Tom head and watching the video and they both were rubbing their cocks through their pants.

Tom pulled his cock out of my mouth and told me to bend over the arm of the couch so he could finish what we started earlier. I handed him some lube and took off my panties before bending over the arm of the sofa and sticking my ass out for him to take. He squirted some lube on my hole and stuck in a finger. I moaned in pleasure as he inserted a second and then a third finger. He was rubbing my ass cheeks and fingering my hole at the same time and I was about to cum thinking of what was about to happen. He positioned himself behind me and slowly slid his cock into me. Starting slowly he fucked me until we had a good rhythm going and then started pounding me good. Our bodies were making a slapping noise as he fucked my tight hole. I was loving this! My semi hard cock bounced back and forth between my legs as he pumped me.

I looked up to see Earl and Jerome were getting undressed. Jerome was the youngest of the three. He was a young black body builder type with a shaved head and some tattoos on his arms. He had big pecs and biceps and a nice fat cock. It looked to be nine inches or better and I remember thinking “finally I get to have a really big cock.” But that was before Earl took his pants off. Earl was the oldest and was a tall and skinny black man. He had short hair and a mustache and his cock must have been eleven inches or better but was not quite as fat as Jerome’s. Honestly it kind of scared me but I’ve always wanted to try a monster cock and since I’ve been fucking men it’s by far the biggest I’ve encountered. There was no way I was not going to try to take him.

By the time they were naked Tom and I had a good fuck going and he was very close to cumming. Jerome got on the sofa on his knees and fed me his cock. I had to strain to open my mouth wide enough to fit him in but managed to get a good portion in and he started fucking my mouth. I relaxed my throat and slowly but surely he started sliding his cock in and out of my throat until he eventually got all of it in. Earl had walked up on my side and started pinching my nipple while stroking his shaft. I reached out and grabbed it and helped him stroke it as it slowly got hard. Tom finally groaned and sunk his cock as deep as it would go before shooting his load deep inside me.

Tom pulled out and came around in front of me and said he needed to be cleaned up so Jerome moved around back to take his turn fucking me while I licked and sucked Tom clean. Jerome lubed his rod and positioned himself behind me. I reached back and spread my ass cheeks apart to make it easier for him to penetrate me. It went in easier than I thought it would and Tom’s cum deep inside me made it easy for him to fully penetrate me. Soon I was taking all nine plus inches of his fat cock as he pounded harder and harder with each stroke. Earl then took his place in front and fed me his monster. Since it was thinner that Jerome’s was it easily slid down my throat. I never dreamed I could take something so long down my throat and I felt like a sword swallower at the circus. Meanwhile Jerome was pounding harder and harder and slapping my ass every few strokes. His huge balls were slapping my taint with every stroke as tears streamed down my cheeks from the throat fucking I was getting.

Jerome soon let out a howl and blasted my insides with a huge load of cum. It felt like I was getting an enema there was so much and when he pulled out a bunch gushed out and ran down my balls and thighs. Earl didn’t waste any time taking his turn. He pulled out of my mouth and walked around behind me. He had me flip over on my back with my head and shoulders on the sofa and my ass on the armrest so it was pointed upward. He pulled my legs up and apart then grabbed his long cock and started feeding it into my hole. With all the cum in me and the double pounding I had just taken he slid in easily and I soon felt his course bush bumping my taint as he slowly stroked in and out of me. He was more gentle than Jerome which was good cause I don’t think I could have taken that kind of rough fucking from this huge cock. It felt great and he was so deep I swear I felt him in my stomach. Our fuck was interrupted though when the doorbell rang. I had completely forgotten that Linda was coming over. I told Earl to pull out for a minute so I could let her in.

Linda walked in and surveyed the room; a naked black and a white guy sitting on the sofa drinking beer and a tall black guy standing at the end of the sofa with a huge erection still wet with lube and cum. She smiled and said, “Looks like you’ve been busy," as she started removing her clothes. I didn’t think this night could get any better but it just did. We were having an orgy now!

I resumed my position on the sofa and Earl soon had all eleven plus inches deep inside me. He knew what he was doing and soon we had a good rythym going with him pulling almost all the way out before plunging back in. It felt so good! He must have been hitting all the right places because I soon shot my load all over my chest and tummy.

Linda who had been sucking Tom off saw this and interrupted her blowjob to come over and lick it all up. I could tell that Earl was getting close so I begged him to pull out and cum in my mouth. After a few more strokes he pulled out and I quickly took my position kneeling before him with his cock in my mouth. I used one hand to stroke his long shaft and the other to cup his balls while I sucked and sucked until he gave me his load. There was a lot of it but I didn’t miss a drop; it tasted so good! It was then that I noticed Linda on all fours on the floor with Jerome’s cock pounding her pussy from behind and Tom fucking her face.

I got Earl a beer and myself another glass of wine and we sat to watch Linda getting spit roasted. Tom fed her a load and soon after Jerome shot one in her cunt. I had to put my wine down and eat the cream pie. I just love a man’s cum mixed with a woman’s juices! It was great!

The fun went on for hours until all of us were done for. We had all fucked Linda in the mouth, pussy and ass and she had been DP’d too. I had been fucked once more by all of them and Linda and I had eaten several cream pies from each other always making sure to share some with each other. The guys thanked us and left and Linda and I limped to my bed and passed out. She said this had been one of the greatest nights of her life.

“Me too," I said before passing out.

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