This is a true story; If you are not 21 or over do not go any further. If you do not like man on man sex go no further.
"If you say so Howard...I trust you".
We heard the elevator doors and Howard turned to the door saying over his shoulder "OK, go fix your makeup and hair and come on out, I'll get the door".
I pranced quickly down the hallway, mostly on tippytoes to my room and closed the door behind me.
I sat on the foot of the bed, knees together, staring at the door. This was an unexpected turn. I heard the doorbell, the door open, and the murmur of the two men greeting.
Sure, I trusted Howard...but not like this, who was I fooling - I was worried. As I sat there my stomach churned and I felt sick. Well I could change quickly and go home, run right out the door, maybe even avoid a confrontation - just run and never look back. Or it could create a scene. Uugh.
I was worried, but not 'a lot' worried. Hell, he's one guy and a tri-state area of millions of people. The chance of him knowing me is practically zero. My engineering mind tried the math: the chance of him knowing me, very low; the chance of him knowing me and recognizing me in this outfit, very low; the chance of him knowing me, recognizing me, and wanting to betray both Howard and me by telling someone else...seemed kinda low. I guessed that if this was a cocktail party with 50 or 100 people, it'd be different, but one friend over for an hour might not be too bad.
And to be honest, I was a little interested to see the reaction of another man. I know Howard thought I was hot, and I did too, but how would a hetero guy see me?
OK, well I knew I couldn't sit there all day so I made up my mind to go with it for the time being. I went into the bathroom to look at myself. Fresh lipstick, wig adjustment, a little primping and preening and I was ready. I stopped in the bedroom and looked at myself in the full length mirror. The cheetah pumps, the tight black pants, the sexy blouse, the lipstick and wig...and thin body...I was hot!
Good, that's the confidence I needed. Trying to channel my inner Kelly Lebrock, I opened the door and stepped into the hallway. I took slow, deliberate steps - short stride, swinging my hips a little and walked into the living room. Both men stopped talking and stood up as I entered the room. Howard's friend was smiling with wide eyes. I resisted the urge to walk right over and shake his hand, choosing instead to stop and stand there with my feet together, hands folded in front of me, as they both took me in.
"Howard, aren't you going to introduce us?"
"Yes baby - Tommy, this is my friend Christine."
I walked forward slowly to him as he smiled and extended his hand, which I shook demurely, with a nice smile. Howard spoke up "It's OK to give Tommy a little kiss, his wife won't mind and neither will he".
Awkwardly, both Tommy and I smiled again...and I moved in closer and brushed my pouty lips against his cheek. He reddened and said "Oh, thank you!".
I walked over to Howard and slipped in next to him, his arm around me on my hip. Howard beamed and said "Don't worry honey, I told Tommy all about us...and you, there's no secrets here".
Tommy looked uncomfortable, like the 3rd wheel. He was also in his 40's, but very different from Howard. He seemed about my height (while I was in heels), was thin & almost frail. His face was pointed, clean shaven, with wire rim glasses. His hair was a mop of dirty brown hair, vaguely parted on the side and he wore a flat fronted grey slacks, a white button down shirt and a blue sport coat with patch pockets. A faded preppy. This was no high priced lawyer or Wall Street Master of the Universe, from my reckoning. School teacher, maybe professor I mused.
Tommy started "Yes, well, Howard has told me so much about you...perhaps not 'everything'" he laughed "but enough to know that you two, are,...are happy together, and that's good".
"And after all my bragging I wanted to have Tommy come see for himself how good looking you really are" Howard said, patting my behind.
We all laughed a bit and Howard deftly followed that by inviting Tommy to sit and relax with him while they turned on the game. As they moved to their seats Howard asked me to help with the drinks.
"Yes, of course - what would you like Tommy?"
"Do you have any beer?"
I shrugged and Howard had to answer "Yes, I have some bottles of Stella in the back of the 'fridge - bring us both one hon, and some chips or something, OK?"
"Yes dear" and I left the room knowing that they were both looking at me...or at least my ass...over their shoulders.
In the kitchen I found the beer, the bottle opener, a new bag of chips and a serving bowl. I filled the bowl with the chips, removed the bottle caps and placed everything on a tray with a few napkins. I carefully lifter the tray and walked into the living room, setting it down on the coffee table and handing the men their beers, which they thanked me for. I recovered the tray and went back to the kitchen.
I leaned back against the counter and caught my breath. Whew! That was OK. Meeting Howard's friend was cool, no problem. I thought that I should join them, so I found a can of coke in the refrigerator, a tall glass and walked out to the tea cart. I found a bottle of rum and splashed it into my glass with the coke, adding a few ice cubes from the bucket.
The guys were already transfixed on the game, so I unobtrusively took my seat next to Howard on the long couch. I sat there on the edge of the seat with my back straight and knees together, sipping my drink and watching the game, wanting very much to look like a beautiful woman for Howard and his friend. I really didn't follow the game much, I wasn't interested in it. The guys talked back and forth and switched channels between 3 different games. When they needed more beer I brought it and refreshed my own drink as well. Somehow it all seemed very normal.
When Tommy got up to use the bathroom, Howard turned to me and took me in his arms, kissing me. "I'm proud of you honey, you look fantastic and you're really acting perfectly".
I was happy and in his arms with my head on his shoulder when Tommy re-entered the room. "Look at you two love birds" he quipped, adding "of course, if Alice and I could be like that once in a while it'd be nice". Apparently things weren't so well with Tommy & Alice. It was an uncomfortable comment that hung in the air, until Howard asked me to bring out some more drinks.
I was well into my third rum and coke and the men were into their fourth beer, enjoying the game. They cheered and yelled together and I was tipsy and happy, just hanging out with Howard and his friend. There was a difference though. Howard and I were happy, and getting a little silly, whereas Tommy seemed to becoming reticent. The 3rd wheel probably felt a little lonely, or sad.
The intercom buzzed and Howard got up, I heard:
"Hello Mr. Weiss, there is a pizza delivery here for you" "Thanks George, we'll be down for it in a minute".
Howard walked over to me digging out two twenties from his wallet and asked me to be a dear and go pickup the pizza downstairs. I giggled and laughed, he couldn't be serious.
"Come on honey, please - it's building policy not to let deliveries in here, you have to pick it up in the lobby, and I'm here with Tommy, I don't want to miss the game".
It was a compelling argument, but even through my buzz I was able to remember that I was dressed like a girl and probably shouldn't. I started to protest but Howard pulled me to my feet and walked me out the door. I didn't resist too much, he was stronger than me and I didn't want to make a scene. "'You'll be fine, five minutes, let's go".
The door closed and I was standing in the hallway. I took a deep breath and strutted to the elevator, praying that no one would join me. In the lobby, I thought I'd have a heart attack. Both George, the doorman, and the delivery guy gawked and outright leered as I walked over. I was scared and hoping it didn't show as I approached them. "You have a delivery for 309?" I asked, trying hard to keep my voice as soft and feminine as possible.
"Yes, that'll be $22.50" he answered. I gave him the full forty and told him to keep the change. I smiled, pivotted and strutted to the elevator. As I left he gave a long whistle and said slowly "That is a...might...fine...tip you gave me lady". I smiled and wondered if he actually thought I was a female or if he was just joking around.
Howard answered the door smiling, and as I walked past the living room on my way into the kitchen, I saw they had the game off and a black and white movie playing...and looked closely, it was the lobby of the building. They had watched me pay for the pizza on the building's closed circuit TV. "It looked like they really liked you" Tommy said and the two of them laughed.
I served the pizza and brought them more beer as they switched back to the game. Howard stood and excused us, and asked me to join him for a moment. I followed him down the hallway and into his bedroom. As he partially closed the door I noticed that his room was clean and the bed was made up. He pulled me into a big hug, grabbing my ass with both hands and pulling me tight against his crotch. He kissed me as he rubbed is crotch against me. "Oh, I've been wanting to do that all night...couldn't wait to get alone with you. I needed to get my hands on that hot ass of yours, you've been flaunting it around in the high heels like such a little tease."
I giggled and rubbed against him. "Can you stay over tonight? I think we're going to be up late and it would really mean a lot to me if you stayed over with me. If Tommy is too drunk he can sleep in your room, and you could sleep here with me".
I was thrilled. I wanted to spend the whole night with him, in his bed. Waking up with him.
"Yes, I'd like that Howard".
"Good, well let's get this party started", he said as he reached over to the nightstand. He produced a small glass bottle that I remembered he called a popper. He opened it and placed it under my nose telling me "You remember how, hold one nostril closed and take a few deep whiffs".
I did as I was told. The vapors flooded my brain and I was instantly cold and dizzy. He held me in his arms to keep me from collapsing. "Yes, that's a good girl, here get some more".
When I was done I sat on the bed leaning against him, feeling my heart pound. His kisses on my neck were electrifying and the most sensuous thing I had ever felt in my life. His hand reached up and started to squeeze at a nipple. I was starting to feel very horny. He trailed his tongue up my neck and whispered in my ear "That hot little bottom of yours must really need some cock tonight, huh?"
"Yes baby" I moaned.
"Good baby, because my friend out there needs to get laid badly and I told him you'd help him out".
I sat back and looked at Howard, trying to focus, trying to think. He interrupted my thoughts "Come on now, you are absolutely gorgeous in that outfit, he needs you so bad, why be such a tease when you know you can help him out...that I want you to help him out?"
"You...want me to?"
"Yes, I want you to invite him back to your room and make love to him, let him make love to you, give him a fantasy come true. Here, take some more now".
A few more sniffs and his touching and talking had me horny and wanting sex very badly. Yes, if he wanted me to, I would do it.
We got up and walked back to the living room. I was dizzy and clung to Howard as we walked. Howard deposited me in the love-seat next to Tommy as he took his seat on the couch. I crossed my legs and leaned over to look at Tommy, putting and elbow up on the backrest. He looked at me staring at him and we smiled. "Are you having a good time Tommy?"
"Yes, you guys have been great".
I felt and intense desire in my bottom for sex, I wanted to get pounded, badly. "That's good, we want you to have a good time. If there's anything you need, you let me know" I said, moving my hand to the back of his neck, touching his ear.
He looked uncomfortable, so I stopped. Howard lowered the volume on the TV and leaned toward us. "Hey Tommy, it's OK, you help yourself to anything of mine." He stood walked past us saying 'I need to go out for some beer...I'll be back in about an hour, have fun". Wide eyed I watched as Howard left the apartment.
Tommy sat frozen staring straight ahead. I placed my one hand back on his neck, the other on his thigh, gently stroking, uncrossed my legs and scooted a little closer. I cooed in his ear "Just the two of us Tommy...and I don't like football...".
He locked eyes with me and looked needy and scared and I so wanted to comfort him. His head dropped and his shoulders slumped. I put my arm around him and pulled him to me, patting him softly "It's OK Tommy, it's just us now".
His arms and hands were clumsy as he held me back...running a hand up my blouse "I want, I want..." he sighed.
"You heard Howard, anything you want..." as I lifted his chin and placed a soft kiss on his lips. He looked into my eyes and stroked the skin on my face.
I stood and held my hand down to him, "Please, come with me".
He followed me, holding hands, to my bedroom. When we entered he quickly closed the door and pushed me against it, squeezing his body against mine, thrusting his groin against me and smothered me with a kiss. He held my hands at my sides by my wrists as he kissed and licked me forcefully. He looked at me, eyes bulging - frantic, needy. "I hope your done teasing me and playing games little miss tight pants" he said with a menacing tone.
"It's OK baby, I'll be good for you" I whimpered starting to feel genuinely scared.
"Good, get over there...face the wall and take off those pants" he demanded.
I walked over to the low dresser and held onto it as I slipped out of my shoes and removed my pants, dropping them on the floor, keeping my back to him as instructed.
"Underwear too" he grunted.
Terrified I slipped the panties down and stepped out of them.
"Put your shoes back on so I can really see how good that ass of yours looks."
"Oh that is nice. Hands on the dresser"
He walked up behind me and grabbed me by the belt I was wearing, tugging my body back and pushing my torso down.
"That's it, bend over nicely for me"
He ran hands over my asscheeks and told me to spread my legs. I did as I was told. I sensed him kneeling down, felt him spread my cheeks and felt his warm tongue immediately on my rosebud, probing to enter it, licking outside it. I closed my eyes and was happy, it was fantastic and I heard myself moaning.
After a few wonderful minutes he stopped and stood behind me, pulling me into a hug from behind. "Thank you" I murmured as his hands roamed my breasts.
"I did that for me, that bitch of a wife I have won't let me do anything like that with her, so I'm going to do it to you".
I was burning with lust as his hands manipulated my body, a hand was running along the crack of my behind, spreading, probing.
"There's something else my wife doesn't like that I'm going to get from you" he growled.
"It's OK baby, you can do it to me, I won't say no, I, I like it"
He had two fingers working their way into my bottom and I was pushing and pulling with my bottom muscles to help draw them in.
"Yes you hot bitch, I feel how bad you need it, Howard told me about that, you tease...well, we're done teasing your going to get my cock where it belongs"
"Yes, please, please"
He dropped his hands and yanked me into an upright position and smacked my bare butt a little too roughly for my liking and said told me to find him some lube quickly. I went to the nightstand and retrieved the box of condoms and the lube, and walked back to him, with one hand cupping my small nuts and cock so he would have to see them.
He was undressing and I stood before him, somewhat dumbly, not wanting to do the wrong thing, not wanting to get hit again.
He undressed quickly, leaving his dress shirt and socks on. As he slipped off his white underwear briefs, his erect cock stood out from his body. It was beautiful, thin, about 5 or 6 inches long, with a pronounced curve. My heart thumped and my bottom was twitching. I wanted to feel that in me soo bad right now, I was actually panting.
"Nice girl" he smirked, yanking the box of condoms out of my hand and tossing them on the floor. The lube he snatched and held in his hand, grabbing my elbow with the other and turning me toward the dresser. "In position bitch".
He grabbed the belt and pushed me in closer this time, resting my elbows and forearms on the dresser. I felt him cramming a handful of lube into my crack and knew he was also stroking his cock with it getting ready to fuck me.
"Please Tommy...this is cool...I won't be a problem" I hurried "but please use a rubber on me".
Wham! Wham! Wham! Wham! "Enough outta you!" he slapped is palm forcefully into my rump, practically lifting me out of my shoes each time.
He grabbed me tightly from behind so I couldn't move, his mouth against my neck, his rigid cock pressing into my crack lengthwise. "You fucking tease, strutting around in your tight pants, waiving this hot ass around, taunting me, 'Oh we're all alone now' you said, fucking tease, 'Anything you want' lying bitch...it's time to give me what I want"
"But I only..."
Wham!
I cried out, tears rolling down my cheeks "Please Tommy"
"Yes, your going to please me, without any more fucking backtalk. I had my tongue on that dirty little ass of your and now your going to take my seed deep into you, we're going to pretend like it's a pussy...better looking that Nichole Kidmans ass, I'll give you that, so you give it up now like a good girl"
"Please, Tommy I..."
Wham! Wham!
His hand was covering my mouth, stifling my cries. "Fucking tease bitch women are all alike. There is only one thing I need and if your aren't going to give it, I'll take it, understand?"
I nodded my agreement, eyes wide with fear.
"Good" he kissed my neck and gently stroked the area he had been slapping "I don't want to hurt you, i just need to get some of what you promised me, OK?"
I nodded and he removed his hand from my mouth.
"Now, there is one thing else I want, one thing that will make this special...will you do that for me?"
I nodded yes, afraid to speak.
"I need to hear one grammatically correct sentence where you tell me what you want and beg me to do to you right now"
He had a hand between my legs, pulling them apart, then pulling one cheek to the side, as he wiggled his cockhead down by my hole.
I thought, I gulped air, I cried, I sniffed. His hand was rubbing agains the spot he had ben slapping, a subtle reminder for me not to get out of line. I whispered "Please Tommy, I know I've been teasing you all night with my hot little body, hoping you'd notice me...I need to feel a cock in me and would love it if you gave it to me...".
He thrust - one long continuous, burning thrust that pushed right past my bottom muscle and had me wincing, crying and up on my tiptoes. My bottom throbbed with hot pain as he held us still for a moment, letting me adjust. He slowly withdrew his cock from me and quickly rammed it in again, forcing a pained moan from me. I was glad for the poppers that Howard had given me, sure that they were masking the worst of the pain.
He slid his hands down and took hold of my hips. He started to quickly move his hips, thrusting in and out of me. His thin waist was obviously part of a wiry core of muscle that he commanded into action, fucking me wilding and quickly. I put my weight on my elbows and pushed back against him, my head hanging low, becoming aroused by the intensity of his motion, hearing out bodies slap together, feeling my soft bottom jiggle with each thrust. I felt his curved cock pushing inside my belly and was becoming very turned on, enjoying it. My whimpering became moaning, then whimpering again...I was lost and confused...and excited.
He thrust hard and held against me with a curse, straining. He withdrew and rammed into me again, and again, shooting his seed deep into my bottom. We froze like that, he was done with me. He withdrew his cock and pushed me enough that I collapsed in front of him. He was panting, out of breath. I was panting too, waves of ecstasy, fear, and pain rolled over me, thinking about what had just happened. I was ashamed., and couldn't look up at him. I reached back to feel my bottom hole - tender, sticky, still loose and open.
"Look at me, get over here" he commanded. I turned to look at him, he stood there holding his cock by the base and was reaching for my head with the other hand. I let him pull my face to his cock, knowing what he wanted. I opened my mouth and took in his cock, smelling and tasting my filth. "Yeah, that's good, that's a good good" he whispered.
I licked and cleaned and was gentle with the head. He stopped me and pulled it out of my mouth, and stood before me batting it softly on my face and chin. I looked into his eyes, hoping to see some compassion.
He smiled a mean smile as he squeezed a thick bulb of cum up his shaft to the head of his cock and slowly moved it to my mouth, which I opened. When I was done he backed up and let go of me.
When he backed into the bed, he sat down and laid back, expelling a sigh of relief. "Whew yeah, that was good baby".
I knew that I had to say something, that I just couldn't sit there, that I couldn't accept this as right, but I was terrified of getting him upset with me. My ass was sore from the sex and I still felt his hand print on my rump from the slapping he gave me.
"I, I..." I choked, "I thought you'd be nice to me"
"You needed that as much as I did you little cunt, didn't you?"
"You didn't have to hit me, I was going to give it up for you, you knew that already" I pouted, looking down at the floor.
He sat up on the bed and looked at me, I looked at him, tears building in my eyes. He looked sad, self conscious, and held his head with his two hands.
"Christine...Chris..."
"Now that you've fucked the hell out of me, let stay with Christine" I said defiantly.
"Christine, I'm sorry, ...I was an ass, I was just so damn horny and, dammit, you looked so hot". He put his glasses on and sat there with his withering cock, rationalizing, looking sad and confused himself.
"Look, I am sorry. I don't get a lot of sex at home - like hardly any, and I thought all you gay guys like taking it in the butt, and you really have a great, feminine body, and that outfit, those shoes, the wig...aw damn, I'm sorry that i fucked this up for you."
That was more of an apology than I thought I'd get, so I took it.
"That's OK...not like I'm giving you an invitation to do it again, but I guess I was a tease, and, and, some parts of it were good too."
He started getting dressed as I sat there. When he was dressed he ambled over the the door and stopped, looking down at me. "Hey, I know I've been a jerk, and I'm way off base here, but if you want to see me again..."
I looked up at him indignantly.
"If you want to see me again, total clean slate - no rough stuff - here's my number, we could get together on the QT after work" he finished holding out a card.
I bit my lip, looking at him. He looked embarrassed and, like a jerk, I felt sorry for him. Against my wishes I felt myself rise and walk over to him, my hands self consciously covering my pubic area. I took the card from him and looked up into his eyes, and smiled weakly.
"Thank you Tommy" and I reached up to kiss him lightly on the cheek. I reached one arm around him and we hugged clumsily and I let out a sob. I felt his cum sliding down my leg and somehow wanted more, wanted to do more with this man, for this man. He knew I was a guy and he still wanted to treat me like a woman. Even now, after he had shot his load and could leave, he was being nice to me and apologizing. Maybe because he knew he should, but also maybe because he wanted to see me again, that he had a need to get laid and wanted my body to please him again.
As we separated I knew it was only a matter of time before I called him up, asking for sex.
End Part 9