Forced to Dress

"Can I have two rum and cokes, please?" The sexily dressed, long-legged, thin brunette asked the bartender, speaking in a deep tone.

"Lose a bet?" I asked the crossdresser who sidled up to the bar and order the drinks.

"I don't want to talk about it." He replied in a husky voice.

"At least you look real good." I smiled at him.

"She dressed me up. I have never done this before." He replied gloomily.

"Well, she has class. Your skirt and blouse match perfectly; sexy shoes and I love the stockings." I openly admired.

He looked at me and almost scowled, "My girlfriend is right over there and I am just trying to get a couple drinks."

"Hey. No offense. It is all good." I said while raising my hands up in surrender.

"If you must know, my girlfriend caught me cheating on her and she is tired of me making passes at women. She figured this would teach me a lesson." He said exasperated.

I looked over to see an amused, pretty young woman, about aged 30, smiling at us as we talked.

"She is pretty. You are a lucky guy!" I say to him, patting him on the back. "How long do you have to stay dressed?"

He looked in her direction, then back at me. "She wants me to experience what it is like to have men ogling and using me."

"Using you?" I asked, very intrigued.

"I don't know what it means either. Hopefully, I won't be too embarrassed or humiliated." He said gloomily.

"Well," I said with a wide smile, "Maybe I can be your first experience."

He glared at me, "What do you mean? You know I am a guy, right?"

I laughed lightly, "Nothing harsh. I will buy your drinks for small recompense. You know, help you break the ice."

"Oh my god!" He said exasperated, "I can't believe I am about to say this," he replied seemingly resigned to his fate. "What do you want?"

I see his girlfriend watching as I put my arm around his waist and slide my hand to his ass, squeezing each shapely globe for a few moments.

She is getting a huge kick out of it as the crossdresser eyed me angrily the whole time.

"That is enough," he said, swatting my hand aside.

"That wasn't so bad, was it?" I asked innocently.

"I can't believe you just squeezed my ass!" He said quietly but still shaken by the experience.

"Maybe that will be enough to sate her appetite." I smiled at him. "Anyway, you must admit you look great. Your make-up really helps you look feminine. I might not have known you were a guy if you did not talk."

"You are kidding me, right?" He looked at me, shocked by my comment.

"No way! Great lipstick and ass, pretty face with all that make up, and you have to admit, you do look hot. Just soften your voice." I said, evening my voice to calm him.

The drinks arrived and he hurriedly grabbed them.

"Hey." I called to him before he scampered off, "What is your name?"

"Sam." He replied, turning to me.

"Your other name," I winked.

"Samantha," he said dejectedly before quickly walking to his girlfriend.

I got a huge kick from the whole experience and watched as he handed his girl the drink and sat at the table. I watched their banter for a couple moments before returning my attention to the game playing on the television behind the bar.

A short time later, I heard the music play and several couples were cheerily moving to the dance floor a short distance from the bar. Among the patrons, 'Samantha' could be seen in tow with his girlfriend and two guys! I chuckled as I watched them dance for a little while, wondering if they knew she was a he. They probably did but liquor changes people's judgment.

I turned my attention back to the game, nursing a couple beers before I felt a nudge.

"Bartender, a couple more rum and cokes, please." A soft voice cooed to the burly but affable man behind the bar.

Sliding my hand around the brunette's waist, I said to him. "You are doing a great job with the voice, Samantha. You are very convincing."

"Thanks. I am working on it." Sam's reply feigned gratitude, not even bothering to remove my hand from his waist.

"Aren't you having fun? I saw you dancing." I dared to pull him a little closer, wondering how much I would get away with, teasing him as if he was a real woman. I was also wondering how much I was daring to go with this guy. Even though he looked good, he was still a male and usually not my first choice for a Saturday evening in this seedy bar.

"You wouldn't believe what Jen is having me do!" He nodded in the direction of his girlfriend sitting with two different guys.

"Why aren't they buying your drinks?" I was so close I could smell his perfume and see the red bra peeking out from the white blouse he was wearing.

"These guys already bought us a drink and I suggested it would only be fair if we bought our own this time." Samantha sounded as if she was going to cry.

"Is the price too high?" I smiled at him, squeezing his side playfully.

"I thought the one guy would fuck me on the dance floor, his cock was pressing between my ass cheeks for half a song!" Samantha looked at me worriedly. "We were dressed, of course, but the experience was so humiliating."

"Wow. I am so sorry." I sympathized, having slid my hand to his hip.

"That is not the half of it. When we sat down, the other guy pushes my hand onto his pants so I could feel his hard-on! Disgusting!" Samantha growled.

"Have you ever done those things to girls you just met?" I inquired.

Sam looked aghast at my comment but then quickly closed his mouth and looked down, "Maybe." He choked out the words.

The drinks arrived and I looked at Sam and gesture I would pay. He nodded and the bartender added the drinks to my tab.

"What do I owe you?" Samantha asked quietly, so only I could hear.

"Hmm." I smiled at him. "Why don't you do to me what you would want, if roles were reversed?"

He turned to see Jen and the two guys talking, and whatever, then turned back to me. "At least let me know your name."

"Joe." I responded simply and slightly opened my legs.

"Okay, Joe." Samantha teased, his fingers starting at my knee and moving slowly upward. "If I was the girl, then I know you would want me to touch you." He squeezed my inner thigh for emphasis.

"But," he looked deeply into my eyes. "If I was the girl, I would want something in return."

"Mmmm?" I moaned and squeezed his ass.

"Not that," Samantha replied, swatting my hand aside. Instead, continuing the tease, his finger tips lightly grazed across my rapidly hardening cock.

"This!" With both of his hands grasping my face, he pulled me into a kiss. Our lips locked for a moment and he sneaked his tongue into my mouth for the briefest of moments.

"Wow!" I responded, beside myself with confusion for having kissed him and I very much enjoyed it!

Samantha smiled broadly, taking the glasses and winking at me before he returned to his table, shaking his butt just a little.

Samantha seemed more relaxed when she sat down and joined their conversation. I turned my attention from them and blindly watched the game and thinking about the kiss.

The game I was watching on the big screen television was nearing the end and my team had lost. I was getting ready to call it a night, looking around the bar to see if Samantha was still around. I did not see him but Jen was on the dance floor having a great time with a new guy.

Suddenly, a hand wrapped around my beer bottle and I watched the sexy crossdresser downing my Sam Adams beer.

"Sorry." Samantha said to me, putting the empty bottle on the bar. "I needed that so bad!"

"Maybe you needed to remove the taste of something." I smiled impishly.

"No!" He said emphatically.

"Spit or swallow?" I asked, knowing he did something to someone.

"Spit!" He hastily stammered in reply.

We looked at each other for a moment before his face became ashen.

"No! I did not say that!" He tried a quick cover-up.

"Okay. Okay." I backed up in my chair and raised my hands in surrender.

"Although," I continued. "You have something right here." I motioned to the bottom of my chin.

I thought he was going to pass out, as he quickly swiped at his chin, only to see it empty with perhaps some rouge.

"You bastard!" He laughed and playfully punched my arm.

"Did you at least enjoy it? Was it your first time?" I squeezed Samantha's ass as I teased him.

"No. Fuck no!" He trembled in his response. "I thought he was going to rape me in the bathroom. It was the only way I could get out of it."

"Jen does not seem any the wiser," I pointed to her on the dance floor. "She certainly does not seem to give a shit."

He seethed, "That bitch! When I told her I had to go to the bathroom, I thought she would join me. Instead, she told Mark to accompany me. He led me right into a stall in the men's bathroom and pulled down his pants. He threatened he was either going to fuck me or I better suck him off for cock-teasing him all night."

He was shaking so much I felt pity for him and gave him a nice hug.

He appreciated the gesture and dried his eyes on the bar napkin as I ordered two shots and two beers.

Samantha was fixing his face, adding rouge and lipstick from his purse when the drinks arrived. I looked inside his purse as he put away the lipstick and noticed condoms and lube. He saw me look and quickly snapped the golden colored case shut.

Clearly in a slightly better mood, we cheered with the beers and each of us took a healthy swig.

Samantha raised his shot of tequila to me, motioning me to do the same. When I declined, he asked why.

"The shots are for you; hopefully they will remove any last taste you may have." I smiled encouragingly at him.

He smiled, thanking me for helping him through this experience, taking hold of my upper thigh.

Placing my hand above Samantha's knee, I quietly said to him, "I will have my shots afterward."

"Are you kidding me?" He replied excitedly or perhaps eagerly.

In subtle response, I only slid my hand under his skirt, caressing the outline of his growing cock confined in lace panties.

"Well, that WOULD cheer me up!" Samantha smiled at me with twinkles in his eyes.

A few minutes later, as Samantha and I flirted with each other, I noticed a couple guys leave the men's room. I motioned Samantha to the bathroom area and after a moment he followed me inside.

I led Samantha to the last stall and we entered quickly and quietly.

The toilet lid did not look bad so I undid my pants and pulled them, along with my underwear, down to my sneakers and sat on the cold plastic seat. Samantha looked worried for a moment until I leaned forward and grasped his panties and pulled them down. He stepped out of them and raised his skirt, showing off his hard five or six inch cock.

Squeezing his sweet ass cheeks and pulling him to me, I closed my lips around his pre-cum dripping cock head. He oohed and aaahed quietly as I sucked him into my mouth slowly, again and again. Samantha's moans of encouragement helped me further please him.

At some point, and I don't know if it was accident or purpose, he dropped his purse and it hit the floor. The contents did not spill out but the purse opened and we both looked inside, noticing the condoms and anal lube. He was beginning to panic but I put my finger to my lips, motioning him to be silent. He calmed down a bit and relaxed even more when he felt my mouth once again cover his cock head and slip the still very hard shaft further between my lips. Using only my lips and tongue and bobbing head, I continued to orally please this sexy crossdresser.

I was so turned on by the whole scene and my cock was incredibly hard I could barely think straight. My hands, however, were busy with their own plan. I was able to blindly take out a condom, quietly remove the wrapper, and covered my cock with the rubber.

Samantha was in bliss, moaning and grabbing my head, slowly pumping his thick cock in and out of my mouth, having me deep throat him at almost every slow thrust of his hips.

I found the tube of easy glide and I squeezed out a decent amount, covering my condom covered cock. Adding more liquid to my fingers, I sought out the crevice between Samantha's really sexy ass.

Samantha froze when he felt my wet finger invade his private region. When he exhaled, I was able to slide my finger a little more inside him. He held his breath and my advance was halted, so I eased it out. I sucked Samantha's cock down to his balls and he exhaled again in pleasure, allowing my finger to penetrate him again; this time deeper.

Samantha quickly caught on to the little game but never stopped fucking my mouth. I would finger-fuck him as deep, fast and slow as he would rhythmically push his cock in and out of my hungry mouth.

Samantha was groaning and I felt his cock swelling as more of his pre-cum seeped onto my tongue. Seizing the moment, I released him and slowly turned him so his cute backside was facing me. I grabbed his hip with one hand, slowly backing him to me and guiding his wet hole to my slick condom-covered and very hard six-plus inch cock.

Samantha turned his head to me and was shaking his head side by side vigorously, realizing what I was trying to do. His lips were close to mine as he was quietly telling me no, no, no. I leaned forward until our lips met. He opened his mouth in surprise and I snaked my tongue between his lips.

My cock head met his anal opening with slight pressure. Samantha broke the kiss but did not move.

"Relax, hon." I quietly cooed to him. "Breathe and relax." I repeated while kissing his ear and neck.

Samantha never broke eye contact with me and I am not sure if he was giving in to his own needs or the position made it difficult for him to maintain. Whichever the reason, I felt the head of my cock tighten as it was squeezing past his anal ring.

His lips covered mine as he moaned and bit my tongue as my shaft penetrated him. Within a few breaths and moans, his ass cheeks were resting on my thighs.

"We did it!" I moaned in Samantha's ear, licking and nibbling on his ear lobe.

"You bastard." Samantha groaned in my ear. "You are inside my ass and I can't help myself!"

As tall as he was, he was able to rise up a few inches and then slide back down on my cock. One of his hands was holding onto the bathroom wall as the other gripped tightly onto my thigh. My hands were holding onto his hips, ensuring we did not lose balance as his bounces became more urgent and more primal.

He thrust his tongue in my mouth and moaned loudly as he pushed my cock inside him repeatedly. Samantha did not stop bouncing up and down as he kissed my face and gripped tightly onto my leg.

I was able to slowly slide my right hand from his hip to his throbbing and bouncing cock. I jerked him hard and fast; keeping tempo with his erratic bouncing and tongue lashing he was giving me.

Samantha moaned and screamed as quietly as he could, "I am. I am. I am cummmmiiiingggg! Oh fuck!! I am cummingggg!"

He slammed down on my cock one final time. My right hand squeezed his cock tightly and jerked hard and fast. I could feel Samantha's cock throb as he shot load after load onto his skirt and blouse and covered my hand with his explosion.

Breathing rapidly and looking deeply into my eyes, Samantha ground his hips and quickly humped up and down on my cock.

"Oh Fuck!" I cried out as quietly as possible as my cum rapidly filled the condom.

Samantha did not slow down until he felt me soften inside him.

After a few moments, he slowly lifted himself from my lap and turned to me as he unsteadily put on his red panties and straighten out his clothes.

I rose and fixed myself up, looking at him the whole time. He looked scared, shocked, and who knows what was running through his mind.

"What is the matter?" I asked Samantha.

"I. I am. My clothes. There is cum everywhere. Everyone will know!" He seemed to shriek quietly. "What am I going to do?"

Thinking quickly, I told him, "There is a back exit right outside the bathroom we can use. No one will see us. We will go to my place a couple blocks away and you can figure out what to do from there. Sound good?"

Nodding in response, we quickly exited the stall and the bathroom. Samantha kept his head down and clutched onto his purse as we exited the building and quickly walked in silence the couple of blocks to my apartment.

Once inside my place, Samantha cried out, "What the fuck did I just do! How could I have let this happen to me?"

I held him for a moment and led him to the bathroom. "Why don't you take a shower and give me your clothes, so I can wash and dry them. I am sure you will feel better after you shower."

He nodded mutely and undressed, motioning me to wait outside for his clothes.

A few moments later he threw his cum stained skirt, blouse, bra and panties out the door and I heard the shower start. I put his clothes in the wash and found some feminine clothes for him to wear.

He peeked outside the bathroom door when he was finished showering and I pointed to the room across from him. He dashed to the room with the oversized towel covering him from calf to neck. I chuckled; such a chick reaction.

I took my shower and walked to the kitchen in shorts and t-shirt and made a couple of watered down drinks, waiting for my guest to exit the bedroom. I wondered how well he would receive the clothes I laid out on the bed for him.

He, I should say, Samantha, did not disappoint!

Cautiously, he eased into the room wearing the black silk robe and matching stockings. He did touch up the make-up on his face, including the bright red lipstick he was wearing tonight. I watched lustily as he padded across the floor to the couch, keeping his eyes on me to gauge my reaction.

"I can't believe the clothes you laid out for me!" He sat down heavily on the sofa, accepting the drink I gave him.

"Wow! You look gorgeous!" I excitedly said, while ogling him.

"You are just telling me that because you want to fuck me again." He responded flippantly while taking a swig of the rum and coke. Although, he did twirl his toes seductively-even if that was not his intention.

I smiled at him, "Are you telling me you want more? You know I do."

"You don't know what I have been through tonight!" He lamented, as he quickly finished his drink and handed me his empty glass.

I gave him mine and walked to the kitchen to make more. "Sounds exciting! Give me some details." I asked while fixing the next one.

"Oh my god! Where do I start?" Samantha wearily responded. "First, Jen forced me to dance with a guy and then it was another. When we finally did sit down, she said I should show my appreciation by jerking the dude off. I was mortified!"

I sat down on the couch next to Samantha, urging him to continue.

"Jen unzipped his pants and pulled his cock out. No one could really see us since we were at a table. She handed the cock to me. I thought the guy would not want another man touching his junk but I was wrong. He only smiled at me, motioning me to continue. I was shaking my head no but Jen gave me that threatening look. So, I did it."

"Wow!" I told him. "Was that the first time you held a cock?"

He looked at me agitated, "Of course! I am not gay!"

"Seems to me you went gay for her tonight." I mused. "I hope she is worth it. So what happened next? Did he cum?"

"Oh he came alright!" Samantha continued. "I did wrap my fingers around his dick and stroked him a couple minutes. Just before he was going to cum, Jen bent down and sucked his cock as I continued to pump. I felt his cum surge through his shaft and watched as Jen sucked his dick deep. I moved my hand and watched as she just kept on sucking more of his shaft into her mouth."

"Fuck!" I exclaimed. "That must have been pretty hot. I mean, if she was not my girlfriend, I am just saying."

Samantha sighed as he took a drink. "I might agree with you except when he was done cumming in her mouth she pulled me in for a deep kiss and pushed his cum in mouth! I spit it out into my glass. She only laughed at me and told me all good girls swallow."