A Coworker and Best Friend Part 2
I become a sissy-slut for a coworker
I had difficulty concentrating during the second day's software training sessions. I was daydreaming about the hot oral sex with my coworker and best friend the night before. She could really suck a cock, and I enjoyed burrowing my face into her bushy pussy. But I also had some second thoughts about what I had agreed to the previous evening after too many drinks.
Tonight, I was going to be Rene's sissy slut in exchange for her being my toy tomorrow night. We both knew this was cheating on our spouses, but we were only going to do the things our spouses deny us. That's our story and we're sticking to it.
We were on a business trip, far from home and staying in separate hotel rooms. When she drove us back to the hotel after the last session of the day, she told me that she had some shopping to do and that I should pick her up for dinner at 7:30. Then she gave me a pair of pink skimpy nylon bikini panties and told me to wear them for our date tonight.
After showering I pulled the panties on. I felt really silly. They barely covered my cock and not having any cloth tucked up beside my balls felt strange, but I had made the promise. So I pulled on boxer shorts over them, finished dressing and went to her room at 7:30. She was wearing the same outfit she had worn during the day and it appeared that she had just returned from her shopping.
When we got in the car, she told me to face the side window and loosen my belt. She untucked my shirt and looked down the back of my pants at my boxer shorts.
"I told you to wear your pink panties!" she said, sounding kind of disappointed.
"I'm wearing them underneath. They feel kind of strange so I put my shorts over them."
She pulled the band of my boxer shorts open and confirmed that I was wearing "my" pink panties, then she instructed me to go to the mens room when we got to the restaurant and take my boxers off. She gave me a small buttplug and tube of lubricant and told me to plug myself and bring my boxers to her.
When I returned from the mens room, she slipped my boxers into her purse and asked me how it felt to be wearing panties and to have something up my ass. I told her that I was nervous and excited and a little turned on. As we had dinner, Rene encouraged me to drink plenty of wine so she could "have her way with me," she said with a wink and a smile. I did as she suggested and it helped a little with the nervousness.
In the elevator on the way back to her room, she was all over my ass with her hands while she pinned me face-first against the wall. I enjoyed the feeling and I wondered whether the hotel security staff was watching on the security monitor from the camera above us. When we got to her room, Rene ordered me to do as she directed because she had done a lot of thinking about what she wanted.
Figuring that she would like it, I said "Yes, Mistress."
I had read some master-slave fantasies, but never really got into the dominant female ones. I was just role playing for her sake. She seemed to like my response so she ordered me to drop my pants and get on my hands an knees. She said that I would need a couple of enemas because she wanted this to be "a clean affair".
She pulled down my panties and pulled out the buttplug. I could tell that she got a thrill out of that but it became obvious that she had a thing for penetrating male ass because she actually squeaked with eagerness when she slipped the tip of a hose into my butt and ordered me to clamp down on it.
When the bottle was empty (and my ass was full), she told me to go into the bathroom and let it out and then come back wearing just the panties. When I came back, I again got down on all fours. This time wearing only my panties and it felt pretty humiliating. She gave me the second enema and then gave me back the buttplug. I returned to the bathroom, emptied the second enema, cleaned up a little and then washed and reinserted the buttplug.
She had laid out the rest of my outfit on the bed and told me to change into it while she used the bathroom to become a man. "And when I come out," she said, "I want you to be a cock-worshipping slut girlfriend who's very happy to see me."
I pulled on black thigh-high stockings and a pink bra that matched the panties. She had left some water balloons for me to stuff into the bra and they made me about a D-cup, just like she is. Then I but on a blouse that fit fairly well and a pleated jumper skirt that made me look like a sexy schoolgirl, if you looked at me from far enough away. I topped it off with a long natural redhead wig. I looked at myself in the full-length mirror and even though I looked ridiculous, I was once again getting kind of turned on.
When she came out of the bathroom she said, "Stephanieeee. I'm home."
I put on my best girl act, rushed up to her like a flirty girl and said, "Oh, I'm so happy you're here! I've been thinking naughty thoughts about you, all day!"
I put my arms over her shoulders and smooshed my boobs against her as she put her arms around me and started fondling my buns. "Ooh, it feels like my ass is gonna be the center of attention tonight." I squealed, "I can hardly wait! Would you like me to suck your cock up nice and hard first?"
When she said yes, I dropped to my knees. She was wearing my shirt and pants so I undid the belt and dropped the pants. There was a big bulge inside the boxers I had removed from myself at the restaurant. When I pulled them down, a big tan dildo popped out.
I tried to be brave as I said, "Wow! It looks like you're planning on giving me a big stretch."
She must have seen the fear on my face when I looked up at her, because she gave me an evil grin and said, "Go big or stay home." I noticed that the straps seemed a little loose, so without even asking I tightened them so her cock was more erect.
"Would you like me to take my blouse off so you can see my boobs?" I said.
I wriggled out of the blouse when she nodded. My fake boobs jiggled nicely in the bra, and she caressed them as I lifted her cock and slipped it into my mouth. I slid my hand up beside her fake balls and found her wet slit. To my surprise, her pussy was now shaved, something that my wife would never do. Her clit was stiff and she moaned as I circled it gently while doing my best to imitate a good blowjob.
"You're such a good little cocksucker," she purred. "Don't forget to lick my balls."
I sucked and rubbed her for a few minutes and then I said, "Oh, I just can't wait any longer. Please fuck me with this big beautiful cock. My ass is all yours."
Rene ordered me to get on my hands and knees on the bed as she stepped out of my pants and shorts. At first, she positioned herself beside me and bumped her cock into my leg and butt a couple of times. She put her hand on my lower back and felt my ass through my skirt. Then she delivered two sharp smacks onto my ass, one on each side. I hadn't thought spanking would be included, but I played along.
"Ooh! That's making my ass so warm and tingly!" It was at that moment that something changed for me. The spanking really woke my cock up and it strained to break out of my panties.
Rene put her hand back on my skirt and then continued down my thigh. It was clear she enjoyed the feel of the skirt and the stockings on me. She slid her hand back up my leg along my inner thigh and up under the skirt. When she touched the bare skin above the stocking I got goosebumps. It felt so... intimate. She rubbed my thighs and then my crotch and then my buns. She pulled my skirt up onto my back and just gazed at her hand as it caressed me.
Suddenly, she delivered five very sharp smacks to each panty-covered ass-cheek. These hits really smarted, but I think her own hand must have hurt almost as much. "Oooch!", I said, "You're making me so horny. I've just got to have that cock inside me. Please fuck my ass." By this time, I was across the line from play acting to really wanting to please my Mistress.
She moved around behind me and I suddenly felt really vulnerable. "Your ass looks really beautiful", she cooed, "Pink is definitely your color."
I didn't know whether the role playing was driving her comments or whether she intended that as really personal, but a compliment is a compliment, even when it's a challenge to your gender identity, so I replied with, "You say the nicest things to a girl."
She rubbed her hand over my warm buns and thighs and then pulled my pink panties down over the thigh stockings, leaving them hanging on my left ankle. She reached between my thighs and stroked my cock a couple of times and then slid her hand back and gave my balls a little pinch. She was letting me know that she was in control and I knew she was enjoying the power she had over me.
She spread my cheeks and I could tell she was looking right at my plugged asshole as she said, "I'm going to love fucking that tight little hole." She released my cheeks and said, "Just relax", as she lubed her rubber cock.
She eased the buttplug slowly in and out and she sounded hyper-excited when she said, "This will help prepare you for the big guy. Now just let it come all the way out and back in." She kept this up until my hole relaxed and I almost couldn't feel it anymore. She pulled the plug all the way out and said, "It's good and relaxed now. It's just gaping wide open waiting for my cock."
I began to worry that it would close again, but as I looked in the mirror, she grasped the dildo just behind the head and slipped it in. She let out a long low quivering moan and I knew that moment had taken on some kind of cosmic significance for her. Maybe even more exciting than when a guy inserts his cock into a girl for the first time.
She eased the cock in slowly, backing it out a little bit and pushing in a little further each time. It just kept going deeper and deeper until I thought I would explode from the pressure. I don't think she wanted me to feel much pain and I didn't want to spoil her fun, but her cock felt so big that I couldn't help but eventually let out a small whimper.
Just then, she gave a short thrust and I felt the fronts of her thighs against the backs of mine and the straps around her hips against my still stinging ass cheeks. My crack was wide open and her balls were now rubbing mine. Knowing it was all in, "balls deep" made it easier to bear and I felt a little proud for having taken in the whole thing.
She slowly pulled the dildo all the way out and I felt the head as it exited. "Your cunt is gaping much wider now," she said as she added more lube to the dildo's head and shaft. She slipped it back in and once again worked it all the way in until her hips again touched my ass cheeks. It went in much easier this time.
She leaned over then and I could feel the weight of her boobs on my back. She reached her left hand around my waist and began to gently stroke my cock and with her right hand, she began squeezing my fake boobs. Then she started to speak very matter-of-factly into my ear.
"My pussy is hot and wet, but you won't be fucking it, because you're a male who is submitting to being fucked up your ass by my cock. It's longer and thicker than yours. I said you're a male and not a man because you're a sissy-boy. You're wearing a sexy little schoolgirl outfit, you have a nice set of boobs and what you're doing is very feminine. You're wearing dainty frilly girlie things, especially those pretty little pink panties that send the message that what you have inside them is destined to be impaled on a stiff cock. You invited my cock into you in every way. You made yourself presentable and you presented yourself. You sucked my cock like a pro and you tightened the straps so I would be able to fuck you good and hard. Your ass cheeks are a beautiful rosy red from the spanking that I gave you as you pretended to be my girlfriend. I forced open your tight virgin asshole and it stayed wide open just waiting for my cock. You now have all of my cock up your ass and you took it like a real butt-slut. Even with all of this humiliation, your cock is rock hard, telling me that you're enjoying this. We both know that all of this is true and that makes you my bitch. I will never again think of you as a man. From now on, I own you and I want to hear you admit it. Tell me that you're my butt-slut!"
"Yes, Mistress, I'm your butt-slut."
"Are you my bitch?"
Yes, yes, I'm your bitch."
"Good, bitch, that's what I like to hear. Now reach back and stroke your puny little pud for me. That's it, bitch, stroke your teeny weeny while my cock fills your ass. Now bitch, thank me for everything I've taught you tonight."
"Thank you Mistress. Thank you for everything."
"Now, tell me you love my cock."
"Oh, I do Mistress. I love every inch of your cock."
"Now, beg me to fuck you."
"Oh please, Mistress, please fuck me. Please fuck my ass hard with your big cock."
She leaned back and dribbled some more lubricant down my crack and onto the strapon. Then she started to give me long hard strokes while rolling her hips gently and I could tell she was grinding her pussy into the base of the strapon. I watched in the mirror as the long thick cock thrust in from different angles - hammering my tender ass while I stroked my cock. Her thighs, hips and balls each made distinct slapping sounds against me as she bottomed out with each stroke and my boobs began to jiggle around from the rythmic thrusts.
"Ohh, Ohh, Ohh, Yesss!"
"Don't cum, bitch. Wait for permission," she gasped. "Ohhh, this is good! I love fucking you. Keep begging."
"Please fuck me! Please fuck my ass!"
"Ohhh, this is so good! I love seeing your rosy red ass with my cock plunging between the cheeks and into your pink hole!"
"I'm your butt-slut! I'm your bitch! You're my Mistress! I love your cock! Please fuck me, Mistress, fuck me!"
"Ohhh, this is gonna make me cum. Don't cum yet bitch! Ohhh, ohhh, ohhhhhhhh, okay now bitch cum. Cum for me while I fuck your ass! Ohhhh, yes, that's it, cum with my cock up your ass!" Ohhh, Ohhh, Ohhhhhhhhhhhhh!"
My load pumped out onto a pillow as we both succumbed to the primal forces that were driving us. As our breathing returned to near normal, she slid a finger into the gob of goo on the pillow and held it to my lips. "Lick this up, bitch."
"Yes, Mistress," I said.
As I watched in the mirror, she watched my ass as she pulled her cock out, catching a little dribble of lube and butt-juice on a towel. She crouched down and watched as my hole slowly closed.
"That was just so sexy," she said.
"Did I please you, Mistress?"
"Yes my little, sissy slave. I loved it. I could get addicted to that, but we're done for tonight. Thank you, Stephanie. You can go back to being Stephen."
I felt a little disappointed when I heard that. I kinda liked being Stephanie. I asked her how she had happened to have a butt plug before she went shopping and she smiled shyly and admitted it was hers. She'd had it since she found it in her mother's drawer when she was in high school. She said she had sometimes even worn it all day at school and later at work. I asked her if she would wear it the next day during the software class and she said, "Yes, Master," with a smile.
We undressed each other and exchanged clothes and I felt a little sorry that she took my pink panties back. As I was preparing to step out the door, she gave me a big hug and thanked me again for helping her have that experience. When I went back to my room, I started to plan the next and final night of our trip.