So to recap… My name is Carl. My girlfriend Tess is shopping in the US with some of her friends which allowed me to dress up gurlie. Tess, of course is unaware of my love of wearing my feminine things and so I only do it around the apartment when she’s not here. I had been using a breast enlargement pump and was now successful in filling my B-cups. Along with my inserts, I gave myself a nice cleavage too.
There was a new adult sex shop opening up and I excitedly wanted to visit it. Dressed in my sexy gurlie things underneath my regular guy clothes, I went. Heidi a sales person spotted me. Since her boyfriend also wore female intimates, she immediately recognized by my slouching posture that I was hiding a similar secret. I made up and told her my girl name was Carlene.
While looking at some plugs and vibrators, Cheryl my neighbour from down the hall spotted me and very quickly realized the items in my basket were for me and not for Tess. Back at Cheryl’s apartment, I was stripped then dressed in some of my new pink lingerie.
I stood in the middle of the living room as Cheryl eyed me up and down like a piece of meat ready to be devoured. I swear there was a bit of drool out the side of her lips. She circled around me dragging a hand along my exposed skin as she moved. “Your skin is so smooth… Baby soft. But your bum is nice a firm especially with the thong exposing them like that. Your legs are very shapely for a guy and look great in those pink stockings. And your boob! Amazing! They really fill that B cup. Put your lifts in and give yourself a nice cleavage!”
The bra had peek-a-boo, padded under-cups so my excited hard nipples poke through. I put in the inserts and adjusted my boobs and cleavage so they almost looked like C’s. Cheryl’s arms wrapped around me from the rear and m*****ed my breasts. I could feel her humping and grinding herself into my back end.
“Carlene! They feel so nice. Almost like a real girl’s.” Cooed Cheryl. She pinched my nipples and made them even harder. “So sexy!”
She dropped a hand between my legs and massaged my little hard-on through my panties. But like her hands touched fire, Cheryl suddenly ceased her fondling. She picked up a box and opened it up. I watched as her slender fingers reached in and pulled out two nipple clamps. It took a minute for her figure out how they worked, but when she did…
With one hand, she pinched and pulled one of my nipples out before she clamped it firmly in place. Fortunately for me, not too firmly. She repeated her process on my other nipple. The two clamps were attached together by an adjustable chain. Then she tightened both of them just enough to make me bite my lip and wince. My cock twitched.
Cheryl stepped back and looked at me pensively. “You need some shoes. What size do you wear?”
“Size 6.” I have small feet for a guy. I added. “Men’s size 6.”
“I guess it’s true what they say about size of feet. Small feet; small cocks!” She chuckled meanly. “Well even my shoes wouldn’t fit you. Do you have shoes at your place?”
“Yes.” I admitted. “I have about seven pairs of shoes.”
“Grab that stuff and let’s go over there.” Cheryl commanded, referring to my purchases. When I went to gather my boy clothes, Cheryl said. “Leave those. You won’t need them.”
Cheryl pulled me by the nipple clamp chain and led the way down the hallway to my apartment. It excited me as her slowed pace would to exhibit me to anyone who came by. When we got to my door she suddenly stopped. “Oops! I forgot your key. You stay here.”
Cheryl slowly meandered back to her apartment. It wasn’t a long time but it felt like days before she returned. She pretended to fumble with the key but finally opened the door. “Anyone come by while you were waiting?”
“No.” I answered as I was allowed to enter; then for some reason added. “Unfortunately.”
I stood in our living room. Cheryl left the door open which allowed a clear shot of me from the hallway. My near naked exposure caused my pre-cum to free flow from my pee hole. “Stay there. Where are your shoes?”
I told her where she could find them. I stood there waiting exposed to the outer hallway. I looked at the front door that started closing. It slammed shut. Cheryl returned. “Did you shut the door, Carlene? Are you embarrassed by how you are dressed?”
“No, Cheryl. I am proud of how I am dressed. The wind always shuts the door.” I meekly answered.
Cheryl gave me an evil suspicious eye and threw some shoes at me. “Put these on.”
They were my favourite pair of red strappies with four and a half inch steel spike heels. I slipped them on and buckled the straps around my ankles.
“I also found this. Put this on too.” Cheryl handed me one of Tess’ fiery red wigs. With practice motion, I bent over to fit it on my head before flipping my long manes back. It was long enough to cover my shoulders. “Matches your pretty pink outfit well. But it is kind of messy. Let’s go brush it out a bit.”
We moved to the bedroom. I sat down at Tess’ dressing table while Cheryl carefully combed out the wig. Of course Cheryl noticed all of Tess’ make-up. I typically didn’t use any since Tess would notice something was amiss and that I usually didn’t have a lot of time to put it on or clean up when Tess was usually out for only a short time.
Cheryl painted on a bright coral pink lipstick with a dark lip liner. She smiled and then she went to town. Full make-up including blush, dark eye liner and shaded eye shadow with false eye lashes and mascara. I looked at myself in the mirror. At first glance, I could get away with portraying a female, but with a closer look it was disappointingly obvious that I was in drag.
Cheryl did not allow me to talk but took time to play with me; put me in different poses and stuff. She tried the other bras and stuff on me but returned to the first things I had on. Then I realized that Cheryl wasn’t trying to embarrass me anymore but was treating me as a living dress-up doll!
She had me lie on the bed and adjusted me into different sexy or slutty poses. Finally while on my back, she knelt between my thighs and pulled my panties down over my tiny cock. “How cute! I wish it was bigger. Too bad. You could have been my new fuck toy.”
Even as hard as I was, Cheryl took all of me easily into her mouth. It felt so good, but then managed to suck in my balls as well. She released her mouthful but then started to lap my asshole. She pushed me knees towards my chest then her extremely long tongue invaded and tickled my bowels. I couldn’t pretend to not move anymore. With my thumb and forefinger, I started jerking myself off while I pinched my aching nipples with my other hand. I wanted to cum!
Suddenly she bolted up like she was struck by lightning. She released me and got off the bed. “Stay there.”
Being her dolly, I pretended not to be able to move. I watched Cheryl as she stripped off. Her long blond hair cascaded over her shoulders as she pulled off her tee. She released her huge firm breasts from the bra she wore. Kind of made me jealous that I had only B’s. She shimmied her generous hips out of her tight jeans and panties before rejoining me on the bed. A la 69, she positioned my head between her knees and lowered her smooth, hairless cunt onto my face. She was pretty wet already as I lapped at her nectar. She lowered her body and took my penis into her mouth again. Cheryl mashed her fat pussy harder into my face; I could barely breathe.
I stuck my tongue into her as deep as I could. I could not hear her but a big gush of juice coated my face; I knew I had made her cum. Cheryl gnashed her cunt into me and came a couple more times. My make-up would be all smeared and I bet I looked like a slut whore after taking it in the face.
“You’re a wonderful little cunt sucker aren’t you? I bet that’s the only way you can get Tess off isn’t it?” Cheryl asked me as she used her hand to jerk me. I didn’t answer right away and she squeezed me hard. “I asked you a question!”
“Yes, sometimes that is the only way I can get her to orgasm.” I admitted. “Otherwise she has to masturbate.”
Cheryl shook her head and snickered. She moved around to the foot of the bed and pulled my panties down to my knees. She took the blue Feeldoe and inserted the blub end into her soppy cunt. She look so amazing with a cock even if it was not real. At least six thick inches protruded from her crotch. “With or without?”
“Uuh..” I had no idea what she was asking me. “With?”
Cheryl looked around the bedroom. She grabbed some of Tess’ la prairie skin cream. The tiny jar was over $400. She laughed as she scooped a huge finger-full. “This is probably one of the most expensive lube you’ll ever have up your ass, Sweetie.”
Cheryl turned me on my hands and knees as I felt the cold lotion against my back hole. She used her finger to push more of it inside me. Then I felt the silicone tip of her cock slowly pierce my ass. Cheryl’s six inches slid into me relatively easily with some slight pressure.
When Cheryl was completely inside, she took hold of my hips and slowly fucked my ass. It was intense. I buried my face into the bed. With every deep stroke in, I pushed back and moaned. “Uuuh…! Uuuh! Uuuh!”
I reached between my thighs and pulled at my tiny erection. Cheryl slapped my ass hard and told me. “Don’t play with yourself! I will let you know when you can cum!”
My ass stung; I cried. “Yes, Cheryl.”
Slowly, she withdrew her cock from me. “Turn over. I want to watch you as I fuck you!”
I rolled over onto my back. Cheryl was between my legs. She reached behind; from the buzzing I knew she turned on the bullet vibrator in the Feeldoe. Cheryl slipped her arms beneath my legs and grabbed my wrists. My ass was open and vulnerable. Cheryl shifted a bit until she aligned her knob against my anus. With a steady push, it spread my hole open.
“You look so fucking hot all dressed up like a little whore cunt.” She grunted to me as she rammed my ass harder and harder. “You like being fucked like this don’t you, Bitch?”
“Yes, Cheryl!” My head was thrashing about. My body was in total ecstasy. “Please don’t stop! Fuck me! Oh please keep fucking me with that huge cock of yours!”
Cheryl seemed to find another gear and plowed my ass even harder than before. The vibrator in her cock was sending shockwaves completely through me. My mouth was open but only gurgly noises came out. “Gaaahh… Gaaahh… Gaaahh…!”
I had no longer had any control of my body. I flopped around like a rag doll each time Cheryl slammed her hips into me. Suddenly tiny, white creamy spurts jettisoned from my pee hole and splashed my face.
Cheryl started to cum as well. “That’s it you fucking whore! Cum all over your face while I fuck your whore ass! Oh yeah! Fuck yeah! Oh god I’m cumming! Oh fuck! Oh fuck! Oh fuck!”
It was most fortunate that Cheryl’s “erection” would never subside. I lost count of the number of positions she fucked me in. I lost count of the number of times she made me cum. My teeny dick hurt so much from shooting air, but her continual ramming my ass made me cum over and over until my entire body collapsed into a heap of quivering jello.
We both awoke the next morning. Cheryl spooned me with her cock inside me; the vibrating bullet died long ago. Cheryl’s hands meandered over my body but mostly m*****ed my breasts and nipples. As tired and sore as it was, my cockette got rock hard. Her hips slowly rocked into me. Long, slow strokes where she pulled out leaving only her knob inside me before pushing it all the way back in. She held on to my puny penis with her thumb and forefinger. Her strokes matched her fucking motion until I came again.
“Morning, Carlene!” Cheryl kissed the nape of my neck. “Did you enjoy my morning wood?”
“Yes, Cheryl. You feel so good inside me.” Then unthinking, I couldn’t believe what I said next. “I wish to be your bitch to fuck forever.”
“Really? Hmmm…” Not sure I liked what Cheryl was thinking. A few moments later. “Let’s go shower.”
I looked at myself in the bathroom mirror. The make-up Cheryl had applied looked like a real bad version of Alice Cooper mixed with ugly clown. After using make-up remover, we showered together. Cheryl carefully washed my body with particular attention to my ass. We dried off and returned to the bedroom to dress. My outfit I wore previously was soaked and crusted with my cum and my stockings were all laddered.
Cheryl selected a different outfit. White bra and panties, garters with white opaque stockings and white stiletto pumps. While she was searching for one of Tess’ blond wigs, she found an outfit that Tess once wore to a costume party; a short white blouse with a short, pleated plaid skirt. Cheryl re-applied my make-up. I looked like one of those slutty, prick-teasing school girls that gave guys tents as they sashayed by.
“Carlene! You look so fuckable, but you know what you need?” Cheryl asked.
“Another good fucking in my ass?” I answered hopefully.
“Yes, that too. Wait here.” Cheryl told me as she went to the living room. When she returned, in her hands was the spreader bar with shackles. “Sit here.”
Cheryl knelt at my feet. She locked the shackles around my ankles and connected the spreader bar between my feet. My legs were spread wide and with my short skirt on, my stocking tops and garter clips were exposed. “There. Much better. Sitting there in such an unlady like position and showing off. It’s a good thing you’re wearing clean panties.”
“Click! Click! Click!” Cheryl had pulled out her cell phone and was taking pictures of me. Just a little insurance in case you change your mind about being my bitch.”
Cheryl bound my wrists together using my tattered, laddered stocking and pulled me towards the bed. It was difficult to waddle with the spreader and high heels but I made it there. Cheryl tied my bound hands to the footboard. “I don’t want you touching yourself.”
She moved behind me and reached around. She unbuttoned my blouse enough that she could pull it open and show off my tits. The bra was a satin with lace trimmed demi-cups that tickled and barely covered my hard nipples. Her hand snaked under my skirt and inside my matching bikini panties. I was unable to stop her sexual assault of me; not that I wanted her to. Pre-cum was free flowing from me and coated her hand. Cheryl brought it to my mouth and trying not to spoil my lipstick, I carefully licked it off. It was amazingly sweet. I wanted more and started sucking her fingers like I was sucking a cock.
Cheryl finger fuck my mouth. When she thought it was sufficiently wet she pulled it out and held it in front of my face. “You know where it’s going next?”
Cheryl lifted the back of my skirt and pulled my panties down over my bum. Her wet finger pushed between my cheeks and into my hole. She pressed against my prostate. I instantly shot a load into my panties. “You silly little sissy bitch! That’s all it takes to get you off?” Cheryl spanked my ass. “Stay there. I want to get something from my apartment.”
“Yes, Cheryl.” I answered, not that I could go anywhere anyways. My legs were trembling with post orgasmic reaction and slight fear with what she was going to do.
I heard Cheryl leave but did not hear her close the front door. I stood there for a couple of minutes before I thought I could hear a creaking noise, then slam. The door shut. I said to myself. “Well at least she won’t be able to blame me.”
Another few minutes and I heard the front door rattle; then a knock and rattle again. “Carl! The door’s locked and I left the key inside with you. I can’t get in.”
“What? I’m all tied up.” I called back to her. “You can’t leave me like this.”
Nothing. No response.
Cheryl did a superb job tying my hands. The knot was tight and strong; there was no way to rips the nylon binds without cutting my wrists to shreds. The harder I pulled, the tighter the binds. I calculated I had a couple of hours to figure out how to get free before Tess got home. I tried and tried but failed. A warm tear rolled down my cheek and wet the corner of my lips. I licked the salty liquid and started to cry more.
There was a rattle at the door. I started to hyperventilate and panic. I called out. “Cheryl?”
I heard the door swing open and someone entered. “Carl?”
“Shit!” It was Tess. I was still tied up and dressed in my skank school girl outfit. “Shit! Shit! Shit!”
“Carl? Are you home?” I could hear Tess walk towards the bedroom. I looked towards the door as she appeared. “Who the fuck are you? What are you doing here? Where’s Carl? I’m going to kill him. Is this what he does when I’m away? Fuck some slut school girl?”
“Uuu… Tess? Please untie me.” I pleaded sheepishly.
Shock crossed Tess’ face as she realized who was talking. Her eyes popped and mouth gaped as she tried to evaluate what see witnessed. “Carl? Carl, is that you? Why… What the fuck is going on?”
“Can you please untie me and I’ll try to explain.” I knew I couldn’t explain anything.
“Auuh… No. You can try to explain to me right now.” Tess stood facing me. She stared at my exposed tits, then. “That’s my school girl outfit. What the fuck are you doing in my school girl outfit? How did you get tied up like that?”
I started to cry again.