I have been cross-dressing in secret since I was in my late teens. Over the years, I have accumulated quite a wardrobe and whenever I get a chance I like to get dressed. When there is little time, I just throw on a sexy bra, panties, and genderless outer clothes like a sweat suit and sneak off to the local adult bookstore in a totally non-passable condition. There I can usually find some dick to suck or someone to fuck my ass.

Sometimes when the family is away, I get fully dressed in clearly female clothes, wig, and make-up as a moderately passable woman. This story is about one of those times.

I had an entire weekend, home alone, from Friday afternoon to Sunday evening in late spring. I started my adventure as soon as I got home from work by stripping off my work clothes, pulling out my secret stash, and heading into the bathroom. First, I shaved my face twice with hot lather to make sure there was not a single facial hair.

Then, I rubbed hair remover with aloe on most of my body. I have been shaving my body since I started growing hair, so everyone thinks I’m just one of those men with little hair growth and don’t question it. I trimmed my pubic hair while I was waiting for the hair remover to do its thing. Then, I wiped the hair remover off with a moist washcloth. The aloe makes my skin feel so soft and feminine. I painted my toenails and fingernails, letting them dry, as I trimmed my eyebrows

Next, I stepped into the shower and removed the showerhead from the hose. I adjusted the water to a small lukewarm stream before pushing the end of the hose into my ass. I held it there for at least ten seconds as it filled my colon until I felt like I couldn’t hold anymore. I turned off the water and waited for a few minutes. Then, I sat on the toilet and expelled the water like a fire hose.

After I put the showerhead back on, I took a shower, washing my hair with shampoo and crème rinse, shaved my underarms, and then used a well-scented body wash everywhere on me. I had to blow dry my hair so I could put on the wig when I was ready. I spent the next hour using an eyebrow pencil, eyeliner, make-up brush, and lip gloss to put on a feminine face.

I don’t know how women do it all the time; it seems like a lot of work. Then I put on the brunette shoulder length straight hair wig and spent another thirty minutes trying to make it look natural. I finished with some expensive perfume that drives me wild.

It was time to get dressed. I put on a red laced thong panty with full front coverage so I could still tuck my junk. It felt so good as I pulled the strap up between my cheeks. I followed it with a matching bra with padded cups that made it look like I had some cleavage when I put my self-adhesive breast forms into the cups.

Finally, I put on a light-colored one-piece summer dress that was almost down to my knees with a deep v-neck. It would surely blow up in a decent breeze. I completed my ensemble with a pair of two-inch heel sandals for a little lift, yet still easy to walk in. There’s nothing like wearing a dress to feel sexy and free. I don’t think women know how lucky they are sometimes.

I packed a small clutch with make-up, money, breath mints, tissues, condoms, and warming lubrication. Now came the tricky part. I had to get into the car and away from the house without anyone seeing me. I timed it so I’d be ready to go as it became dark. But, I still had to be quick and careful. Taking one last check to make sure I had everything, I opened the front door, looked around, and walked to the car. I didn’t waste any time backing out and getting on my way.

It was about a half-hour ride to the bookstore, not too close, not too far. I got there a little before nine o’clock. There were not very many cars in the parking lot for a Friday night. I walked in and went directly to the theatre. They don’t charge for females or female impersonators.

There were only five or six men in the main viewing room. I sat down toward the back hoping one of them would come over and sit next to me. There was no movement among any of them. I got up and walked around the booth area. One man was standing alone in the hallway. As I passed him, he asked, “How are you tonight, Honey? All dressed up and no one to blow.”

I stopped momentarily and answered him, “Maybe,” then proceeded down the hallway expecting him to follow me. He just stood there. I’m not sure if he asked me a question to tell if I was a real women or he was another asshole. Either way, it was probably best. There was something about him I didn’t like anyway.

I roamed around for twenty minutes without finding anyone interested in anything, let alone fucking me. I spent so much time today preparing for this, including an enema. I went back to the main room and sat in the front row with my legs crossed, waiting for some more prospects. I couldn’t believe how dead it was and the lack of interest by the few that were here.

I thought about other options like the park and the rest stop. There was too much risk at the park. Not everyone likes cross-dressers, some like to beat the hell out of them. The rest stop can be equally dangerous and was another forty-five minutes away.

Finally, after almost an hour, a man walked in, spotted me, came over and sat next to me. He looked at me and said, “It’s like a ghost town in here tonight. I guess everyone went to the motel orgy advertised on the internet this week. How are you doing tonight?”

I thought I was going to cry as I answered him, “Not so good. I’ve been sitting in here for an hour by myself.”

He replied, “Such a shame. You look so good. What are you looking for?”

Almost pouting, I said to him, “I just wanted to get fucked. I don’t get the opportunity to go out like this too often.”

“You like getting fucked? Ever been gang-banged?”

I told him, “I was fucked twice in the same night here a few years ago. But I’ve never been gang-banged.”

“Would you like to try it? I know a place I can take you about twenty minutes away. I guarantee you’ll get fucked and I will make sure you’re safe. Are you interested?”

While I was somewhat suspicious, I was also desperate. I hesitantly agreed saying, “Yes, where are we going?”

“We’re going to an all-male farm labor camp out in the blueberry fields. I went to high school with the owner’s son. You can call me Dude, everyone else does. They don’t have the facilities for a coed camp and there are too many problems if they did. In fact, you can make a few bucks at the same time. Well, are you in? You can take a picture of me, my car, and my license plate, and then send it to an e-mail address for insurance.”

I followed him out to his car. It was a late model beamer. I took the pictures as he suggested and sent them to my e-mail address. Then, I got in his car. As we drove, he continued to assure me that he would be with me the entire time and all I had to do was say stop, if I wanted to stop at any time. I felt like a prostitute. Actually, I guess I was going to be a prostitute. I was getting excited at the thought of what was coming.

We pulled onto a dirt road between the rows of blueberry bushes and drove a couple hundred yards to a white stucco building. The doors were open, the lights were on, and there was reggae music playing as fifteen or twenty black men were sitting outside the front of the building. We parked off to one side near a wooden picnic table with attached benches.

Dude said, “Wait here, I’ll be right back.” I sat on the table bench while he walked over to the crowd of men. A few minutes later he came back to the car, opened the trunk, and took out a sleeping bag. He unzipped the sleeping bag and laid it out on the top of the picnic table as he said, “This is for you.”

A minute later, one of the men walked over to us and handed Dude some money, as he said in a strong island accent, “You’re right man, she is pretty.” Then, he walked over to me, put both his hands on my shoulders and rubbed them down my arms, on to my waist, and around my butt. He looked over to Dude and said, “She smells good, too.” Much to my surprise, he also smelled good. I guess I was expecting him to be sweaty and dirty. He must have just taken a shower. Then he smiled at me and said, “Are you ready for me little lady?”

I responded by pulling his sweat pants down and putting both my hands on his cock. I had been waiting all night for this and I wasn’t going to be denied another minute. I began jerking him off with both of my hands getting him hard. I pulled him by his dick a few feet to the bench so I could sit while I continued to get him worked up. He must have grown to a beautiful eight inches.

I had to have him in my mouth first. I took a lick on his tip. It was like catnip to a cat. I plunged it into my mouth until he was at the back of my throat. I moved my head back and forth, sealing my lips on his chocolate shaft. He put both his hands on my head urging me for more. I leaned down a little, raising my head, to improve my angle. I pushed forward forcing him into my throat. He let out a groan.

Then he pulled out. “Is this a bonus or the grand finale?”

“What do you want it to be?”

He answered, “Do you have a condom, sister?”

I stood up, walked to the car, and grabbed my clutch, bringing it back to the table. I took out a condom and ripped off the wrapper with my teeth. I rolled it on to his dick. I stood against the end of the picnic table with him standing in front of me. I took my plastic bottle of warming lubrication and squeezed a generous amount on to his dick, rubbing it around the tip.

Then, I leaned back onto the top of the table with my legs hanging off, before raising them straight up in the air as my dress dropped onto my stomach. I pulled my thong up, exposing my ass, but covering my dick. My ass was perfectly positioned on the end of table as I said, “Well stud, what are you waiting for?”

He stepped forward and lined his cock up with my waiting hole. He held my thighs with his hands to pull himself into me. The heels of my feet were against the top of his chest. I could feel the cool wet lubrication on the end of his cock against my anal ring. His grip on my thighs tightened lifting my ass off the table a few inches as he kept a steady push forward until the tip of his dick spread my sphincter open allowing his shaft to glide into my colon. While he wasn’t the largest cock I ever had, he was respectable. My ass felt full and satisfied. I liked this position because he had to do all the work and he could control the pace as he wished.

Once he was in me all the way, he began to move his hips back and forth sliding his shaft halfway out and back in, with the emphasis on the forward thrust. The cold warming lotion began to heat up inside me from his friction. We were looking into each others eyes watching our effect on one another. His face changed from a serious look to a smile as he continued to fuck my ass. At one point he looked away for a moment. I rolled my head in the same direction to see another man standing near us watching. I gave him a little smile as I turned my attention back to my current lover.

He began to increase his pace and the smile on his face turned back to a more serious look. He was breathing through his mouth now and his eyes were almost closed. He started making a low grunting noise at the end of each thrust. He stopped briefly to pull my body back to the end of the table. His constant thrusting had driven me away from the end. My ass and lower back was completely in the air as he was now hugging my thighs. This caused my cheeks to squeeze tightly on his cock. My ass was on fire as the warming lotion continued to gain heat from the constant and increased friction.

His face began to contort, his eyes were shut, and he was panting like he just ran the four-minute mile. He made three more long thrusts, the last one being held, as I could feel his cock twitching inside me. He let out a giant gasp confirming he came. After a minute or two, his grip began to relax. My body began to rest on the table. As I rolled my head a little to the side, I saw the same man, again, that was standing there a few minutes ago. He looked at me, smiling, as he said, “I am next.”

I fumbled around for my clutch with my one hand. The man picked it up and gave it to me. I fished out another condom and handed it to him, “Put this on.” Then I pulled out the warming lotion, “And put this all over your cock before you put it in my ass. Okay.”

He smiled and replied, “Okay, honey.”

The man still in me said to the other man, “Your turn, come take these legs.” He pulled his dick out of my ass while holding my legs up. My ass suddenly felt empty. I could feel the cool night air on my anal ring as it must have been dilated open for a short time. The second man held my legs up as the first stepped away. He pushed his cock in my ass with little resistance and started moving it in and out immediately. I was glad I gave him more warming lotion. He was moving in me quite easily and the temperature was rising, again.

This man was on a mission. He started out fast and continued that way for fifteen minutes without slowing. I often use warming lotion for lubrication since it seems to make my partner cum faster. While I love getting fucked in the ass, I have had a few men who went on for an hour until we were sweaty and I became dry inside. There’s no enjoyment in that.

My ass quickly became hot from the fast and intense motion. This guy must have been shorter than the first since I was flat on the table as he pounded away on me. Also, my feet were on his shoulders instead of his chest. He didn’t make much eye contact. But, he kept his pace until he declared, “I’m cumming, little honey.” I wouldn’t have known it if he didn’t say it out loud. I couldn’t feel him tense up or pulsating inside me. He stayed in me less than a minute after he came. He gently lowered my legs down after pulling free.

I stood up, pulled up my thong, and pulled down my dress while I rested a few minutes. Dude asked me if I wanted a cigarette or a shot of whiskey. I told him I’d take both. I smoke only on rare occasions, mostly when I drink. Tonight was definitely going to be one of those occasions. He handed me a cigarette and gave me a light. After I finished the cigarette, Dude gave me a swig from his bottle of whiskey as he said, “Here comes another one. Are you ready?” I told him I was ready as he walked over to meet him near the front of the car.

A few minutes later, number three walked over to me, “What you got, mama?”

I shot back, “What you want, man,” in an imitation Jamaican accent.

He pulled down his pajama type pants and said, “I need you to get this off.” He was holding one of the longest dicks I ever seen in person. It must have been ten inches long, yet not too big around. I put both my hands on it, one next to the other, and it still stuck out a little.

I jerked him off a little to see if it was going to grow or get harder. It became a little stiffer. I sat down on the bench and put it in my mouth. After sucking on it a few minutes, I dove down and forced his snake dick into my throat. It bent with the contour of my throat allowing me to take him deeper than I have ever gone before. I kept it down at least twenty seconds before giving it back up to take a breath.

He exclaimed, “Damn, mama, you are good. Can you do that, again?” I took a deep breath and took him down my throat, this time bobbing up and down, fucking him with my mouth. He grabbed my head and used his hips to try and continue the throat fucking. But, I had to pull up to get some air first. I took another breath and put my hands around his waist signaling him to drive it back in.

My throat must be more sensitive than my colon as I could feel the length of his cock inside. He pushed so far I thought he was going to reach my stomach. We did this several times before he asked, “Can I try the back door now?”

I stood up and got another condom out of my clutch. I rolled it down his dick until it was completely unrolled. There were still two inches of uncovered dick. I rubbed some lotion over the condom. Then I leaned over the end of the picnic table on to my stomach spreading my legs apart. He pulled my dress up over my ass and pulled my thong down in the back. I held the edge of the table with my hands as he pushed the tip of his dick into my ass.

He had to wrap both of his hands around his shaft to keep it from bending as he fed it into me. I could feel the nubs of the condom rubbing the inside of my anal ring. I always like that feeling and this time it seemed to go on forever. Although I was concerned about how far it was possible to push a dick into me without doing any damage, it didn’t stop me from trying to find out tonight.

Finally, I could feel his legs against mine. I couldn’t believe there were almost ten inches of dick inside me. He held my hips with both of his hands before he started pushing and pulling it in and out. His cock slid freely since it wasn’t too big in diameter. While there wasn’t as much friction, the warming lotion was covering a larger area due to his extended length in my colon. The heat was building deep inside me and it seemed like it was warming my whole body. His extraordinary length allowed him to take longer strokes than I have ever experienced before. Each stroke was like being fucked all over, again. I began to moan quietly without any control.

Before I knew it, I came like a racehorse all over the sleeping bag. My colon began to spasm. It was the first time in my life I had an anal orgasm. I didn’t think it was possible. The front of me was a sticky mess. Once, again, my ass was on fire as the long strokes were generating intense heat the length of my rectum. It must have started to have an effect on him as he began panting heavily.

Then he began to cry out, “Here it comes, mama.” He gripped my hips tightly pushing in as far as he could, holding that position. I could feel him recoiling inside me. He exclaimed, “You’re the hottest mama I have ever seen.” He leaned on top of me as his knees began to buckle a little. “Give me a minute to get off you.”

As I waited, I turned my head. I saw another man watching and waiting for his turn. I reached out for my clutch, pulled out another condom, and waved it in front of him as I instructed him to put it on. He took it from my hand. A minute later, snake dick stood back up and pulled his cock out of my ass. Then he said, “Oh-oh, the condom did not come out.”

This has happened to me a few times before when smaller dick men soften before pulling out. They slide out of the condom leaving it hanging out of my ass. I just grab the part hanging out and pull it from my ass. When I reached back I couldn’t feel anything hanging out. In a panic, I pushed my finger into my ass. I could feel the rim of the condom.

I pushed it against the inside of my anal ring as I pulled my finger out. I pulled just enough outside that I could pinch it between my thumb and forefinger. Then I pulled the condom out of my ass. I stood up in relief and tossed the condom in the trash can. I couldn’t believe how full of cum it was.

I went back to the table, checked the condom on the next man, and lay on my stomach, again. I forgot about the large cum-slick I left on the sleeping bag. It was cold and wet. The waiting man pulled my dress back up. My thong was still down. He quickly found what he was looking for as I could feel him penetrate me almost immediately. He was more average in size and girth.

He gripped my waist and began pumping away. It took him about fifteen minutes and he didn’t say a word the whole time. It was a very uneventful fuck. He hardly made a sound when he came, pulling out as soon as he was done, and walking away without a word.

When he was done, I stood up as another man walked over. I opened my clutch and discovered there was only one condom left. I yelled to Dude that this was my last condom. He said there was still another customer. I yelled back, “Not without a condom there’s not.”

The man standing next to him said, “How about a blow job then?”

I answered, “Okay, come on over.” I turned to the first man and pulled his sweat shorts down to his knees. His dick must have been at least eight inches long and bigger around than I could hold with one hand. It was a good thing that I always carried the extra-large magnum condoms. He was too big for a standard condom. I rolled it on him and then rubbed a large amount of the warming lubricant on him. I knew I was going to need it. I put both knees on the bench and leaned over on the tabletop on my stomach. My thong was still down. I looked back and said, “You know where to put it.”

He lifted my dress up in the back and stepped in. He spread my cheeks with his hands as he lined up his dick with my overworked service entrance. As he started to push, he warned, “This is gonna hurt, little girl.” At first, he couldn’t get it into me. His cock started to bend before it could force me open. He backed off before pushing, again. He started grunting as he had to push several times before he could open me up enough to penetrate me. When he finally gained entry, we both sighed. I didn’t want him to know I felt a little pain. However, once he passed through my ring, it was pure pleasure from then on.

When he bottomed out, I motioned for the other man who was watching us, and waiting his turn, to step in front of me on the opposite side of the table. He had on only his boxer shorts and slippers. I pulled his boxers down. He was already hard from watching us. I wrapped my hands around his waist and pulled him into my mouth. He was medium-sized so I could deep throat him with little effort. I love getting it at both ends at the same time. It makes me feel submissive, yet desired.

The man in my ass was pushing in and out. His thrusts pushed the other guy’s dick down my throat. When he pulled back, I withdrew the dick in my throat. We started to develop a rhythm controlled by my ass fucker. He wasn’t fast and furious. He made long slow strokes which pleased all three of us. His hands were holding on to my hips as he used them for handles. The man in front of me had his hands on my shoulders. I continued to keep my arms wrapped around his waist as we went on for a while like this. We must have attracted an audience as I could hear several voices around us.

The hands on my shoulders began to squeeze tight. A minute or two later he said, “I’m gonna cum in a minute.” I never had a black man cum in my mouth. So far I liked the taste of his dick, so I was anxious to taste his sperm. Like most men, I think his announcement was a warning, in case I didn’t want him to cum in my mouth. He seemed to relax his grip on my shoulders. However, I increased my hold on his waist pulling him into my throat so there was no doubt about my intentions.

He let out a grunt as he tensed up. His vein began to pulse against my tongue as it pumped its first load down my throat. I pulled back so I could breathe and so I could taste him. There’s no taste when a man shoots his load down your throat. His second load was coming out as I was pulling back coating my tonsils and the back of my tongue. I had my lips on the tip of his cock as his third dose spurt into my mouth. I began to suck to get whatever was left in his thick vein. “Ohhh mama, you sucked me dry.”

A voice in the background commented, “She swallows. I hope she will take a little more.” The man in my mouth pulled out and stepped back, pulling up his shorts, while I swallowed his cum. I gave him a big smile.

I could now see there were three men standing in front of me. My ass was getting hot from the methodic fucking while my dick was hard, pressed against the sleeping bag on the tabletop. couldn’t be more excited sexually. When one of the three men in front of me asked, “Can cum in your mouth?” as he was jerking off.

I didn’t hesitate to hold my hands out and say, “Come to mama. I’m thirsty.” He stepped up to me with his dick in his hand guiding it toward my lips. I opened my mouth as he put it in while moving his hand up and down his dick at a frantic pace. In less than a minute he began to shoot the biggest load of cum I ever had. He completely filled my mouth as I swallowed while he still managed to pump one last stream. I took a second swallow as he pulled it out of my mouth.

The other two, without asking, walked up, also jerking off, as one said, “Are you ready for some more chocolate love juice?”

I looked up with a smile, “I’m beginning to love chocolate.”

He responded with urgency, “Open your mouth wide, baby.” He held his cock about six inches away from my face as he shot his load in three forceful spurts. He finished by rubbing the tip against the corner of my mouth removing the leftover dribble.

I closed my mouth and swirled his sweet juice with my tongue savoring the taste and texture before swallowing it down. The oral sex was a good distraction since I was still being fucked in the ass for almost thirty minutes now with no sign of completion.

The last man in front of me said, “I’m ready to fill your mouth now. Open up for me.” His cock was huge. I could hardly get it in my mouth. I don’t know how I would have gotten it in my ass. He was using both of his hands to jerk off. He shot a pretty good load filling most of my mouth before pulling it out. “How would you like this big boy in your ass sometime?”

I swallowed the mouthful of cum before replying, “Maybe next time.”

My attention returned back to my rear entrance where I was getting hot and dry. I reached for the lotion and held it behind me. In a sweet feminine voice, I asked, “Would you mind lubing me up a little more? I’m drying out, stud.”

He said, “Okay, little girl. Am I hurting you?”

I said, “No, you’re just wearing me out. I need to walk, again, after you’re done giving me a bigger asshole.”

He pulled his swollen cock from my ass and squeezed the lubrication all over it. Then, he pushed it back into me. The lotion was cold and soothing at first, but quickly began to heat up as he continued to pound me. The renewed lubrication allowed him to slide in me, rather than push and pull my dry colon back and forth. Suddenly, I began to have another orgasm as my dick shot my cum onto the sleeping bag. I let out a loud moan and my colon began to spasm.

This must have excited my lover as he started grunting. He gripped my hips tightly and pushed his cock in as far as he could. As my spasms diminished, they were replaced with the throbbing of his cock inside me as it pumped the condom full of his cum. He leaned on me as he collapsed a little from almost a solid hour of fucking.

I was lying in a pool of cum, with the taste of cum in my mouth, my dress pushed up, my panties pushed down, and eight inches of prime cock in my ass. I don’t think it can get any better than this. He rubbed his hands on my back over my bra straps, probably imagining, like me, that I was a woman. After a few minutes, he pushed himself back, standing up. He pulled my thong up and my dress back down. I slid my knees off of the bench and stood up.

My knees were a little stiff and my ass a little sore. I turned around and sat on the bench. I helped him slide the condom off. There was a coating of cum on his softened cock so I put it in my mouth and licked it clean before pulling up his boxers. I walked over and threw the condom in the trash can. As I walked back, he met me halfway, giving me a big hug.

“Thank you, little lady. I enjoyed that very much.”

As he walked away, Dude walked over and asked, “How are you? You’ve had a busy night.” He handed me a small stack of bills.

Several of the group waved as we got into the car and drove away. I counted the money Dude gave me. I made $120.00 for having the time of my life. I thought to myself: “Blueberry fields forever”.

Dude said, “If you ever want to do it, again. Let me know.”

I replied, “How about tomorrow night.” He smiled and gave me his phone number when he left me off at my car. The taste in my mouth and feeling in my ass lasted through the night and into the next day.