Florida Vacation


I was in Florida, on a break from my job and visiting friends. I was staying in a dive motel in Pensacola Beach and visiting different people each day. Each evening I would return to the hotel and then plan the next day's visit that evening. There wasn't much to do after that though and my mind started to wander.

I imagined myself going out and buying a few women's outfits while I was there. I had been dressing for many years now and even brought some panties and a bra with me on the trip. I always liked to dress when I travel, even making sure I have panties and a bra on when I drive on a weekend trip.

I felt brazen because no one knew me in this town and if I paid in cash, they wouldn't know my name. So what if I got a few weird stares, I would never see those people again. So the second day after visiting my friends who lived to the east, I drove back and stopped off at a K-Mart. I walked all through the store and couldn't bring up the courage to buy anything. I hopped back in my car and moved along.

The next store I stopped at was a super Wal-Mart. I wandered through the store and noticed they had self-checkout lines. That was the push I needed. I could scan and bag all the goods I was going to purchase. I still didn't have the courage to select items from the women's department, but I did pick out three things. It was Halloween time, so I picked up a barmaid's dress and a wig, then two t-shirts to put on either side and hide the fact that I was carrying a women's costume around.

I made my way to the checkout, got into a short line, and scanned and bagged my items as quick as possible. I got back to the hotel and immediately tried on the dress and wig. It felt smooth against my skin and I stayed dressed the rest of that evening.

The next day, after visiting my next group of friends to the west, I found another super Wal-Mart on the way home. This one was in a shady part of town, so there were no self-checkout lines. I wandered the women's wear and then headed to the Halloween section. There was a greater assortment of costumes, including some short dresses for adult women. One particularly caught my attention. It was a sexy maid's outfit. I went and picked out a pirate costume, then grabbed the maid's outfit and another little dress for a pixie and made my way to the checkout.

I got into the shortest line, but the woman in the front ended up taking forever. I just stood there nervously, going over a story in case anyone talked to me. However, being a stranger, no one did. When I got to the checkout, the cashier just scanned the three costumes, bagged them, then handed me my receipt and I went on my way.

I made it back to the hotel and grabbed the bags with the costumes out of the trunk. I started to make my way along the outside corridor to my door when three black guys came out of a room a few doors down from mine. They started walking my way, obviously heading for the parking lot. As I passed them, I turned slightly so we wouldn't bump shoulders, and the first guy looked down to make sure he had clearance from me and my bags. He stopped and I could see him looking through the clear plastic bag which was on facing him. I looked down too and noticed you could see right through and read the cardboard attachment describing the maid's outfit and in an adult women's size. I was even with the third guy when I realized the first one had turned around and had begun to follow me back towards our rooms.

I got to my door and he came up and asked if I planned on wearing the maid's outfit soon. I don't know what possessed me to confirm that I was, but the words came out of my mouth. I slipped my card key into the lock and pulled it out. I saw the green light illuminate and then saw the first black guy's hand open my door and step inside. He went in and sat down at the desk that was next to the bed. I followed him in and then heard the other two file in and then close the door.

I was told to put on my costume and model it for the three of them. I was so horny at this point that I did. I went into the bathroom, slipped on the costume, my panties, and the wig. I came out in the black maid's outfit, black panties, black long hair, little silky cuffs, a headpiece with lacy trim, and a little fake duster.

I saw the guy at the desk unzip his pants and pull out his cock. He told me to come over and clean his dirty rod. I went over, bent over, and began dusting it with my fake duster. It started to rise and I estimated that it was halfway erect at five inches after my dusting. He told me it was still pretty dirty and might need a spit shine.

I dropped to my knees in front of him and began to lick up and down the length of his cock. This got him all the way erect and his long black cock stood ten inches to attention. I gave his shaft a thorough licking, then took his head into my mouth and circled it with my tongue. I licked around the edge and then spent some time pressing the tip of my tongue into the slit of his cockhead.

The leader, who had his cockhead in my mouth, then stood up and told me he was going to treat me like a golf ball washer. He grabbed the back of my head and began moving his hips so that he was fucking my mouth. I understood the ball washer reference as my mouth became the hole filled with liquid and he was driving in and out of it to get his cock cleaned.

With each thrust, he tried to drive his cock further into my throat. I gagged on each attempt for the first twenty or so, but then began to relax and let his cock slide down my throat. A few minutes later, he was long dicking my mouth. He would pull out until only his head was in my mouth, then drive his shaft inside me until his balls were on my chin. He would pause there until I would look up at him, then he would pull out again. Finally, I just stared up into his eyes and he just pounded away on my mouth, driving down my throat followed by a withdrawal to the edge.

I managed to take breaths through my nose when he would pull his cock out of my throat, but they were short breaths with the break neck pace he had begun to set. After what seemed like an eternity, he had only his cock head in my mouth when I felt a flood of cum begin shooting. Thankfully, he didn't drive forward again, but just let my mouth fill with his seed. When he had drained himself totally, he commanded me to show him how much I had. I did as ordered and then swallowed it all when he told me I had to. It felt thick and tasted salty, but not as bad as I was expecting.

The leader tucked his cock away and the other two guys stood up. He grabbed my hand and pulled me to the doorway. He opened the door and the four of us walked outside and toward the parking lot. He told me that they were heading to get food when they came upon me and that they were going to go know. I was obviously along for the ride.

The leader let go of my hand when we got to the car, but it was shortly grabbed again by his buddy. He led me around to the passenger's door and opened it. He slid into the bucket seat, used his free hand to slide the seat all the way back, and then pulled me inside so that I was on my knees in front of him. The third guy jumped into the back.

The car was started and the guy in front of me unzipped his fly and fished out another monster cock. I grabbed it with one hand and guided it into my mouth. I started sucking him off, taking about half of his nine inches into my mouth. When I felt comfortable though, I let his shaft slide down my throat like I had been taught to do by the driver.

I felt the car stop and start like we were at traffic lights, then turn and pause with the engine running. The driver asked everyone for an order and I realized he had gone to a drive through restaurant. I kept on sucking his buddy's cock while the order was placed. The driver made sure to ask for a special order. Once complete, he informed me that I was to keep sucking, but be sure to angle my head towards him so the takeout window person could be sure to see me with a huge cock in my mouth.

We pulled up to the window and I saw a young looking kid there in shock at what he was seeing. The driver just asked him if he had ever seen a white slave girl before and they all started laughing. I saw the kid go back for some of the order, then return with two other friends and a girl. Everyone wanted to see the white maid with her mouth full of cock. They all watch me staring at them as I deep-throated the guy in the passenger's seat.

A few minutes later, the complete order came. Surprisingly, as the driver was paying, so did the guy I was sucking. He pulled out of my mouth and came all over my face. His first shot hit me in the forehead, his second in the right eye as I angled my head back. I could feel the rest flying into my open mouth, then the rest dripping down over my top lip. Some of the shot that hit my right eye trickled down my cheek and onto my neck.

I scooped some of the cum away from my eye as we pulled out of the burger king. The passenger kept his cock aimed at my mouth and made me lick his cock dry as we drove back to the hotel, or so I thought that's where we were going. I just continued to have a long make out session with the passenger's cock while each of the guys ate their food.

Eventually, we came to a stop and the guys got out. I was pulled out and realized we were at a sex shop. We went inside and the leader bought a few items, including breast forms, fishnet stockings, high heel stilettos, make-up, and some anal lube. The shop keeper helped outfit me with a great set of 36c's and then let me put on the stockings, stilettos, and some make-up in a mirror he had out back.

I came back and looked a little different, much more feminine and sultrier, although the cum dried on my face and neck certainly added to that persona. The guys thanked the shopkeeper and we headed back into the car. This time I was dragged into the back with the third guy.

Once inside, he pulled me so I was lying across his lap. He lifted my dress, slid my panties aside, and pulled the anal lube out. I then felt a lubed finger penetrate my ass. Then another and another. Soon I had his three fingers sliding in and out of my ass, finger fucking me until I was nicely loose back there.

Once I was nicely primed for him, I was turned so my back was against the seat and facing forward. He unzipped his pants and pulled out his cock, a fat eight incher. He applied some lube to it, then lifted my legs up and put them on his shoulders. My little ass was fully exposed to him as he slid my panties aside once more. I felt his cockhead at my doorstep, then watched as it disappeared beyond my outer boundaries and felt his cock begin to fill me up. It took him some time to ease all the way in and I didn't think my ass could stretch to fit his girth, but he was slow and let my ass distend until I would allow him to slide further in. Once completely buried, with his balls against my ass, he peered down and smiled. I was so hot at watching him slowly slide his cock all the way inside me that my own cock was fully erect inside my lace black thong.

Then he began to fuck me. He pulled halfway out and then drove all the way back in slowly. He did it again a moment later. Then again as I looked down and saw his thick black cock emerge from my insides, then disappear. He was standing up and leaned over the top of me with my legs near the top of the back seat. I had my hands to the sides to balance myself, but as he picked up his pace I positioned them on his hips to help drive him all the way inside me. I was barely aware of the stops and starts that the car was making as I got my once tight little asshole reamed in a way I never knew possible.

Time seemed to stop as I stared into my lover's eyes, much like I had done while blowing my other two boyfriends earlier. I could feel my loose asshole being fucked deeper now. My lover was pulling his cock most of the way out of me, then driving his log back inside. Every couple of minutes though, he would change and just jackhammer my ass with shorter quicker thrusts.

I really started to breath heavily now and could feel some sweat dripping down from his chest and hitting my new fake titties. I pulled down the top of my dress to expose my new nipples and then felt him bury his cock all the way inside me.

A torrent of cum filled my insides and I exploded into my panties too. We climaxed together and then he collapsed on top of me. My hamstrings were burning from the extreme stretch they were getting and he finally pulled out and slid in next to me in the backseat. I readjusted my panties, but felt them begin to get soaked immediately from the pool of cum leaking from my now widened asshole.

We pulled into the hotel and I was shakily helped out of the car. I was led behind the leader down the corridor and into their hotel room. Once inside, I was thrown down on the bed on my stomach. The leader grabbed a pillow, shoved it under my hips so my ass was off the bed, pulled my sopping wet panties aside and shoved his rock hard cock inside me.

He fucked me hard while I grabbed another pillow and used it to muffle my moans and screams of pleasure. He was a little longer than the first guy to fuck me, and a lot rougher. He had his hands on my shoulders at one point, slapping my ass at another. At one point, he sat on my ass and pulled both my legs up one at a time until he guided my hand around the heel of my stiletto. I was bent back while he held the small of my waist and fucked me hard.

When I got into this position, the last guy to fuck me jumped on the bed in front of me and forced his cock into my mouth. The two guys found a rhythm where they both stuffed their cocks all the way inside me at the same time, then pulled out at the same time. When they were both inside me, I had nineteen inches of cock inside me.

The leader finally came inside me and pulled out. The guy in my mouth buried his cock inside me until I felt like I was going to pass out, then took it out completely. He turned me onto my side, slid up behind me, and easily shoved his nine-incher in. He also fucked me hard, holding my arms back and forcing my fake titties out. At this, the first guy to fuck me started to shift and I could see he was getting aroused again. He stripped down naked and I saw his rock hard eight inch cock standing straight up and ready for more action.

My ass was getting pounded as the first guy got on the bed. He pushed me so that I rolled onto the guy fucking me. He spread my legs so that they were on either side of the hips of the guy who had nine inches buried in my ass now. Then he crept forward and guided his cockhead against my extremely lubricated and extremely loose asshole. It took much longer than the first time in the car and hurt ten times worse, but eventually he got his cock buried inside me along with his buddy. I thought nineteen inches in my ass and mouth was bad. I now had seventeen in my ass alone.

At this site though, the leader jumped on the bed and kneeled by my head. He guided his half limp cock at my lips and let me lick his shaft while his buddies lifted me up and then pulled me back down on top of their cocks. I couldn't feel anything as my asshole was numb now, but knew I was amazingly being fucked. To add to it, the leader's cock was now erect from my tongue caressing and he guided it into my mouth. I was sucking his cockhead, and being pounded by his buddies.

We kept this up for a long time until I felt the guy under me begin to buck and flood my ass. Shortly thereafter, the guy on top of me followed suit. The leader let his buddies out and then pulled out of my mouth and jacked off all over my face as I lay there exhausted. He released a smaller amount of cum right across my chin.

Then the three guys showered and got dressed and went out. About an hour later, I built up the strength to stand up and leave the room. I got into the corridor outside and headed down to my room. I keyed in, wiped the cum from my face, licked it off my hand, swallowed it down then fell face first onto the bed and passed out.

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bydysfunctionaldreams© 13 comments/ 176565 views/ 28 favorites

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