When I woke up the next day I was hit with guilt and shame. Bo was gone and I laid on my back, staring at the ceiling. I was dressed in the white silk nightie, and the pink bra and panties from the night before. My ass was sore from the pounding and my face was caked with leftover makeup. I felt bad physically and emotionally and so I started to cry.
This is not what I had wanted and now I couldn’t really get out of it. If I said anything to the RA or to my parents, the whole world would think I was some sexual deviant—some pervert who couldn’t go away from home for one night before he dressed up like a woman and blew a guy. Abby and Bo had it all on tape, but what was the worst part about it was that I was so willing to do it. All it took was a little attention from a pretty girl and my life was ruined.
My mind kept going in circles that morning. Will it be social suicide for me, where I admit to what I did, probably lose a lot of my friends and family, lose my girlfriend and likely have my tuition pulled from my parents? Or will it be social homicide, where I let Abby and Bo take control of me, turn me into whatever kind of sex puppet they want and see where I end up at the end of the year?
I picked up my phone and saw a bunch of missed calls from my girlfriend, Emily. She must be going nuts. One night away and her boyfriend was already gone. She must’ve spent the whole night crying.
I couldn’t handle the guilt. I decided to call her and tell her what was going on. I’d leave school, start somewhere else in the spring semester and take a mulligan. What was I thinking last night? What was I thinking when I thought I could handle this?
As I swiped my phone open, I heard a key enter the door. I turned around and saw Abby enter. I remembered she said we’d be getting started early today, but now I’d made up my mind and I was gone. No more of this.
“Hey pretty girl,” Abby said.
“Abby,” I started, sitting up in the bed. She closed the door and looked at me.
“You know that’s not my name, Ali,” she said.
“That’s what I need to talk to you about,” I said. “This is all a huge mistake. I know I was playing along last night but I just can’t do this.”
I started to cry. Abby, to my mild surprise, came and sat beside me on the bed. She put her arm around me and wiped my tears from my cheek.
“Shh, baby,” she said. “It’s OK. We don’t have to do anything you don’t want to.”
“It’s too late,” I said. “I can’t be here anymore.”
Abby ran her fingers through my hair and reach back to pull a tissue out of the box. She dabbed my eyes, picking up the tears and mascara that was dripping down my face. Abby looked me in the eyes and smiled and said, “OK, just relax.”
I composed myself eventually, feeling no better or worse than before she got in there.
“Are you gonna be OK?” she asked sweetly.
“Yeah, I just, I just need to go home,” I said.
“Why don’t you lay down. Let’s stay in today,” she said.
I lay down on the bed, getting back under the covers. It was better than whatever she had originally had in store for me. I was really grateful for Abby’s sweetness. She was acting like a friend again.
“Do you mind if I lay with you?” she asked.
“No,” I said, a little happier. “Come on in.”
She stood up and pulled off her sweatshirt. She was wearing only a shiny yellow bra, which propped her breasts up and made them jiggle with each move. She then pulled down her shorts, revealing a white thong. I remembered the image of her pulling her pants down from yesterday, and how hypnotizing the curve of her pussy was underneath her panties. I was staring as she climbed into bed, and embraced me from behind.
“Let’s just lay here for a while,” she said.
I was more than happy to do that. Her tender sweetness and physical openness reminded me of how wonderful a thing a friend is, and how loving a woman can be.
We dozed in and out of sleep that morning, always with Abby having her arm around me. When we both opened our eyes a few hours later, Abby kissed me on the neck, and asked, “Feel any better, sweetie?”
I did. Maybe the night before was just some game she wanted to play. She was a freshman too after all. I mean, maybe this is her form of experimenting and that she wanted the same things I wanted—to make friends, hook up and have a good experience. I could see that.
Abby kissed my neck again and slid her left hand from my chest down to my crotch. She rubbed her hand gently over my cock, which was still encased in lacy pink panties. It felt so nice to have this beautiful woman in her bra and panties rubbing my cock and showing me tender affection. I turned around and we met lips. She let me slide my tongue into her warm mouth. She shifted the position of her hand on my cock and started rubbing it with upward motions. It instantly grew to become fully erect, sliding sideways to stay encased in my panties.
Abby broke off the kiss and giggled.
“What do you want me to do?” she asked.
Where was this last night? This chick was clearly into domination and submission equally, which it struck me might be just exactly what I was into. I clearly liked being dominated yesterday, even if things went entirely too far, and I was really enjoying taking control of Abby. This could be the start of a really rewarding experience.
“Suck my cock.” I said.
Abby giggled and worked her way down to my dick. She lifted up my slip and kissed my smooth chest. When she got down there, she kissed my cock through the panties. Eventually she took the tip her mouth while it was still encased in the silk, and then pulled the edge of my panties over the cock. My erection sprung free and Abby kissed the shaft up and down sweetly. I put my hand on the back of her head as Bo had down to me the night before and she engulfed my entire cock in her mouth. We simultaneously moaned in delight. I looked down and was enraptured by the sight. A beautiful brunette in a lacy yellow bra and thong taking my entire dick in her mouth. She looked up at me with her stunning eyes and I knew I was close. I wanted to blow my entire load into the back of her throat and prove to her that I wanted to be dominant now and again. If she wanted to see if I could hang, switching control back and forth, as some sort of test to see if I could be her boyfriend, I’d show her.
“You ready, bitch?”
“Mhm,” she murmured, her mouth filled with my cock.
I prepared to shoot my load when suddenly she pulled away. She sat up on her knees, gorgeous as ever, looking at me.
“Aren’t you going to cum?” she asked.
“Aren’t you going to finish, bitch?” I asked, trying on a dominant voice.
She laughed. “No,” she said. “Well, yes. But first you have to earn it.”
Here we go again.
“What do you mean earn it? I told you I’m not doing this anymore,” I said, sort of lying because I was on the edge of cumming, with a stunning chick in front of me and I would’ve punched my mother for her to suck me for just 10 more seconds.
“You do everything I say today, and I’ll finish you off,” she said.
“What do I have to do?” I said.
“It’s nothing like last night,” she said.
“Can’t you just finish me now and then I’ll do whatever you want?” I said.
“I can’t trust you to do that yet, dummy,” she said cutely.
“How long will I have to wait?” I asked.
“Oh, not long, we’ll be back before dinner,” she said.
I thought.
“Do I have to go out dressed as a girl?” I asked.
“Nope,” she said, smiling.
“OK, let’s do it,” I said, feeling like I’d won a small victory and excited to see what this new version of Abby had in store for me. More than anything, I felt like I had 50 times the amount of my normal testosterone and adrenaline coursing through my veins, imploring me to do anything necessary to get off.
“Clean off your makeup and put on some boy clothes. They’re in the box,” she said. “I’ll be back in 20 minutes to pick you up.”
I got up from the bed when Abby left and pulled down my panties and lifted off the slip. I undid my bra and placed everything in the clothes bin. I pulled out a pair of boxers, jeans and a T-shirt from my boy clothes box and put them on. I grabbed a hat and pulled it low over my face so no one would have to see me in makeup while I walked to the bathroom.
I washed off all of Abby’s work, peeling off a few bits of dried cum from the night before. I finished cleaning and went back to my room to wait for Abby.
She came by a few minutes later and entered the open door. She was wearing a pair of black shiny leggings with a loose black tank top. She had her hair in a pony tail and her makeup was minimal but striking. She closed the door, undid my jeans, pulled down my pants to my knees and started sucking again.
I immediately regained a full erection and felt like I was on the edge. I grabbed Abby’s ponytail and forced her head down the full length of my shaft. This was it.
“I’m gonna cum,” I said, loosening my grip on Abby’s hair. She pulled off and said, “Alright, pants up. Let’s go.”
She said it so matter-of-factly and had switched gears so easily from cockslut to mistress that I stood a little dumbfounded. She had turned on that switch in men that makes them do irrational shit if they don’t cum. It’s an overwhelming feeling, to be on edge for a long period of time. Your mind becomes locked solely on pleasure and there’s an incredible energy that transforms you into somebody on a mission. The thing is, I didn’t know who was in charge anymore. I was back dressing and acting like a guy with a beautiful chick sucking my dick every 20 minutes, but here we were going to do whatever it is she had in store. She’d changed the chemicals in my brain to control me through my dick.
The difference between this and last night, though, is this is the type of control I can get behind.
We hopped in Abby’s car and drove about 20 minutes to the big mall on the other side of town.
“Now look,” she said as we got out and started walking toward the entrance. “You have to do whatever I say and only then will I blow you, OK?”
“OK,” I said. “What are we shopping for?”
“You,” she said. She pushed me up against the nearest car and stuck her tongue deep in my mouth. She took my hand in her hand and slid it down the front of her shiny leggings. I felt the warmth of her pussy and started fingering her. She moaned and leaned back from our kiss and bit her lip. An old couple walked by and I pulled my hand out and we giggled. I was rock hard.
“Anything I say, got it?” she asked.
“Got it,” I said, so goddamn turned on.
“No questions asked or the deal is off,” she said.
“Let’s go,” I said, ready to get over whatever she had planned.
We walked into the mall. It was a Saturday and the early afternoon so it was pretty busy, mostly packs of high schoolers and other college kids. Abby slipped her hand into mine and started to lightly pull me in directions. We veered off the main walkway into our first store, Victoria’s Secret.
The whole place was a tart’s dream. Pink interior with satin wall fixtures and chandeliers. And of course all the lingerie, bras and panties any girl could want. There were packs of young girls walking in and out hurriedly through the store. We stopped in the doorway.
“OK, so here you’re going to pick out a bra, a pair of panties, a garter belt and some stockings,” Abby said, letting go of my hand.
“Are they for you?” I asked.
“Yeah, they’re for me,” she said, laughing. “Were you not there last night?”
“Abby, I told you, I wasn’t going to do this,” I said.
“And I told you I’d let you cum in me if you did everything I said without any complaints,” she said. She leaned over and started to whisper. “Now we can leave right now, go back to the dorm, post that video of you dressed up like a sissy slut blowing your roommate on Facebook and you’ll never get to touch me again. Or you can do what I say and I’ll finish you off.”
My brain said no, but cock said yes.
“OK,” I said.
“Good girl, Ali,” she said loudly. I blushed when a couple girls looked my way. “Now this is what you’re going to do. You’re going to go up to that cute salesgirl and asked to get measured.”
“Abby,” I started.
“Listen,” she said firmly. “You’re going to get measured, then you’re going to pick out your lingerie. You will hold up several pairs of panties to your waist to see how they look. You’ll ask the salesgirl if you can try your little girl clothes on. Then when she asks if you’re doing alright in the dressing room, you will say ‘Yes’ and ask if you can wear the clothes out.”
I looked at Abby and exhaled.
“You want this,” she said. “You want me.”
“Are you coming with me at least?”
“Nope, I’ll be on the bench out here making sure you’re doing a good job.”
I sighed and walked into the store.
“Can I help you sir?” the young salesgirl asked. She was wearing tight black pants and a black shirt, and obviously a push-up bra from the store. I looked at Abby who gave me a “go ahead” motion with her hand.
“I was wondering,” I whispered, embarrassed, “if, uh, if you could measure me for a bra and panties.”
The young blonde with perky tits laughed in my face.
“Uhh, if that’s what you want, hun,” she said. “You serious?”
“Yeah,” I said, blushing.
She laughed and started walking toward the back, waving me with her.
“You get a lot of men in here?” I asked trying to make conversation as she took a tape measure to my chest.
“Yeah, but they’re usually shopping for their wives or girlfriends,” the salesgirl said. “Are you gay?”
“No,” I said offended.
“Well then why are you buying a bra for yourself?”
“It’s complicated,” I said.
“Are you a drag queen?” she asked. A group of teen girls walked by on their way to the dressing room and one said, “Looking good, girl!” and laughed.
“No,” I said.
“Are you going to a costume party?” she asked.
“No,” I said, wishing she would just drop it.
“Then why am I fitting you for a bra?” she asked.
I didn’t really know how to answer her. Why was I really getting fit for a bra? I couldn’t say it’s because a mistress told me to. That’s more humiliating than just saying it’s for me.
“OK, it’s just cause I like it,” I said. “I’m a crossdresser.”
“Do you want to be a girl?” she asked.
“Yes,” I said, exasperated. “Is that good enough?”
“I’m sorry, hun,” she said. “I was just trying to get you to open up about it.”
I felt bad about snapping at her.
“It’s OK,” I said. “I’m just a little embarrassed.
“You don’t need to be,” she said, giggling. “You’re going to be a 36-A, but if you want to stuff your bra, you can probably get a B or a C.”
“Thanks,” I said and walked out of the back room to pick out my clothes.
“I’ll be right with you to help you out,” she said.
As I walked out, I passed display after display of bras and panties. I had no idea which one I wanted, but I just wanted to get out of there so I stopped at the nearest stand that caught my eye. I remembered Abby’s instructions to hold panties up to the mirror, so I picked out a pair of lacy black boyshorts, a blue satin thong and a stretchy red pair. I held each up to the mirror and looked self-consciously around. I caught a middle-aged woman looking at me and she quickly averted her eyes.
“Do you think any of those panties are going to hide your junk?” the salesgirl asked, coming from behind.
“I wore this exact pair last night,” I said, pointing to the boyshorts, “and they fit fine.”
The salesgirl giggled. “How about a bra?” she asked. “I have a bra that’ll go perfectly with that blue thong.”
“That’ll work,” I said. The salesgirl reached down and pulled open a drawer. Inside was a light blue bra with white lace trim and shiny light blue straps. In the middle was a girly blue bow with a diamond in the center.
“Pretty, right?” she asked. “Shall we try them on?”
“Uh,” I started. “I actually wanted to get a garter and stockings, too.”
“Oh,” the salesgirl laughed. “Big night, huh?”
“Come on,” I said sheepishly.
“OK, OK. You go try these on and I’ll bring you a garter and a pair of thigh highs.”
“Great,” I said, taking the bra and thong from her, glad to be out of the main floor.
I went back to the dressing room and took the nearest empty stall. I locked the door, took a deep breath and started to take off my clothes. I slide the satin thong up my legs first. When the material reached my cock, I started to get hard. It had been teased with so much all day that the first sign of femininity got it going. I tucked my cock back and picked up the bra. I put it on backwards and then slid it up to my chest. I had fastened it tight, as Abby had done for me, and propped my chest into the cups to simulate breasts. It kind of worked. I was too tall for the mirror and so my head didn’t show, but the body that was on display in the light blue satin and lace bra and panties was feminine and hot.
The salesgirl knocked on the door and entered my stall.
“What are you doing?” I asked, embarrassed.
“Oh, please,” she said. “I go in with every girl. I can leave if you want.”
“No, it’s fine,” I said, letting my guard go down. “It’s, uh, fine.”
“Hubba hubba,” she said. “You really look alright, hun.”
She handed me a matching blue garter belt and a pair of sheer white stockings. She fastened the belt for me, “This would take you forever,” and I sat down to slide the stockings up my legs.
I’d never experienced the sensation of the stockings on my shaved legs. It felt oddly erotic. The salesgirl fastened my garter to my stockings and said, “There.”
It looked good and I took turns rotating in the mirror to check out my ass, which looked nice with a satin thong in the middle of it.
“Alright, take those off and I’ll ring you up,” she said. “What name should I put for the register?”
“Alex,” I said. “Er, no. Uh, Ali.”
“Ali,” the salesgirl said. “Right.”
“Oh, wait,” I said as she was leaving. “I was wondering if it was possible to wear these out?”
“Well,” she said. “You have to put clothes on top of them so we don’t all get arrested for indecent exposure, but sure. Let me just take the tags and I’ll meet you at the register, Ali.”
I put my clothes back on. The outline of my bra was clearly visible through my shirt and my panties stuck out when I bent over. The stockings also obviously popped out of the bottom of my jeans. Oh well, the task was done.
I left and paid for my items, catching a few more giggles on my way out. I saw Abby sitting on the bench and she perked up when she saw me.
“So I did it,” I said, walking toward her. “Can we—”
Abby cut me off and lifted up my T-shirt in the middle of the mall to see my bra. She held it there and I tried to push the shirt back down, but she wouldn’t let me.
“Wow,” she said. “Nice choice. I don’t think I have a bra this nice.”
“Abby, please,” I said.
“Just let me see your panties,” she said, unbuckling my pants and peering in. “Oh, wow, satin. You slut.”
“Are we done now?”
“Two more stops,” she said. “That’s it. We’ll be out of here in an hour.”
I swallowed my pride and took Abby by the hand as she led me down the mall aisle. We arrived shortly at the entrance of Forever XXI.
“We’re going to go in here and pick out an outfit for you,” she said. “We’ll have to find something to go with those slutty white stockings, so I’ll help you this time.”
Before I could protest, she took me by the hand and dragged me into the store. I didn’t care anymore at this point. The humiliation at Victoria’s Secret was about as much humiliation as one guy can get, so this was all a cakewalk. It’s like when you win the lottery, picking up a dollar on the floor seems meaningless—I’d reached my humiliation capacity and my ability to feel shame was broken. In a way it was liberating—to not care what people thought of me. Plus, at the end, I was getting a blowjob. And most of all, I think Abby was really into this and pleasing her seemed like what any respectful boyfriend would do. Am I making this seem more normal than it is?
“I got it,” she said, excited. “To commemorate the loss of your virginity, we’ll put you in white!”
“Whatever,” I said. Abby pulled off a couple white dresses and held them up against me. Some of the older girls in the store were looking at me and were a lot more judgmental than the ones at the other store.
Eventually Abby decided on a stretchy, tight cocktail dress, with thin shoulder straps and a miniskirt. It had cream and white colored sequins on it, which made it sparkle. The back of the dress went all the way up to my nape, but the neckline in front was low.
“Good thing you got a push-up,” Abby said. “Let’s go try it on.”
We went into the dressing room and I took off my clothes. Abby smiled when she saw me in the lingerie. She helped me into the dress. She had gotten it in the largest size, because I’m so tall, but it was still a little short. It reached to just below the top of my stockings. Anytime I bent over in the mirror, the light blue garter strap would show.
“This is going to be good,” she said, adjusting the straps up top, which were about an inch thick and hid the bra straps underneath, at least while I was standing still. “I’m going to go get you some shoes, stay here.”
Like I was going to go somewhere.
I danced around in the mirror, running my hands over my new curves. It all felt good because I was being held in some tantric sex state thanks to Abby, and my cock began to get hard again in my panties. Abby came back a few minutes later with a shoebox. Inside the box was a pair of velvet blue heels, the kind where the fabric turns them into wedges. They were hot as hell. I slipped on the pair and kicked up my heel like a girl in the mirror.
Abby clapped enthusiastically and said, “That’s a look.”
“Do I have to walk out like this?” I asked.
“What do you have to be afraid of?” she said.
“Uh, looking look a fool,” I said.
“Babe, you look better than I do,” she said. She same over and pressed her body up against mine and kissed me deeply. She then got down on her knees, lifted up my dress and pulled my cock from the satin thong. She took it in her mouth and I felt that energy again—that energy that made nothing else in the world matter besides blowing a load inside this girl’s mouth. She pumped a few times on my dick and pulled back like the last time. I was kind of enjoying the energy at this point. “I’ll go pay for this. Meet you outside.”
I waited for my boner to subside a little and slid it half-erect back into my panties, which almost made me cum right there. The heat of my dick touching my asshole reminded me of the pleasure I felt last night when I was getting pumped in the ass. For as much as I felt guilty about it, there was no denying the pure physical fact that it felt incredible.
I pushed open the door and walked out to the store entrance. Abby kept me waiting for a few minutes, so I stood on the corner, trying to pose as feminine as I could. If I was going to look like this, I’d rather try to come off as a girl, or something like that, rather than fight it and humiliate myself as a man. A few young girls came by and started a conversation with me, clearly wanting me to be their gay friend and help them pick out clothes. Abby came out and said, “Alright girls, Ali’s got an appointment, she’ll talk to you later.”
Abby took me by the hand and led me back into the mall. I still looked like a 6’4″ freak man in my heels and without a wig or anything, but the sight of us two together definitely turned some guys’ heads. Maybe they were just wondering what a hot chick was doing with the tranny.
“One more appointment for you, little miss,” Abby said, pointing to the Sephora makeup store. “Go in, say your name is Ali and that you have a makeup appointment. I’ll be downstairs at the kiosk picking out a wig for you. No more cum in mine.”
I walked into the Sephora glad that this was not only my last duty before I could fuck Abby, but glad that makeup and a wig would be added to my look so that I could at least hide who I was. Everyone could’ve seen Alex, the freshman dude, wearing a dress and shopping for panties. Who knows if I’ll get recognized in the future.
“Hi, I’m Ali, I’m here for a makeup appointment,” I told the nearest salesperson.
“Ali!” the girl said. “Right this way. We’ve been waiting for you.”
I sat down in front of a big, lighted mirror and two makeup artists came over to work on me; one guy and one girl. They chatted about what the best thing would be for me, saying I had girly cheekbones and a feminine chin, but that my eyebrows were a problem and they needed to make my sunken eyes pop. They just assumed I was a girl. Rather, they treated me like a girl. It was refreshing to not have to explain it to other people and to just be accepted for what I was.
What I was. Who knows what that is.
They got to work, applying layer after layer of makeup. In thirty minutes, they had done their job and stood back feeling accomplished. What I saw in the mirror was different than what I saw last night. They had transformed me. As I was marveling at the look, Abby came up behind me and put a long, dark brown wig on my head. It had some wave to it, and fell just below my shoulders. The makeup guy then went behind me and started arranging the hair. He tossed much of it over to one side, brushed it out, clipped some parts and eventually pulled the whole thing back into a loose bun with a large bang running down the left side of my face. It was elegant and feminine, and I loved the look.
“Well done, guys,” Abby said. “Anything to say, Ali?”
“Thank. Uh, thank you,” I said, still admiring myself, now fully turned on by the image in the mirror thanks to the level of arousal I’d maintained all day.
“She’s excited,” Abby said. “She has a big night.”
“I bet she does,” the guy said. “Good luck, honey.”
“Thanks,” I said, mindlessly.
I walked out of the store with Abby and the looks were different. I was still self-conscious and obviously I wasn’t a woman. I was too tall and my shoulders were too broad. I walked like a man, too. But I embraced this new identity. This person who took femininity to a new level. Who, though he isn’t a woman, chooses to embrace the things that make women so beautiful. It was sex that I was selling. Feminine power that only comes from being able to make guys do whatever you want because they think with their dicks and not their brains.
And that’s when I looked at Abby and realized she had turned me into her. She was my sister, not my fucktoy. This was the big game, and my suspicion early on that this was all a rouse, that nothing had changed and that she was always in control, was correct. But I experienced it first hand now. I didn’t need to be told or scared into it. I wasn’t operating out of fear anymore; I was operating out of my own free will, powered by the electric energy of sex she was charging me with.
We got into the car, and every time I caught myself in the mirror on the drive home I remembered what my relationship with Abby had become. She was my sister, my mistress, my girlfriend. But more importantly, she had transformed the way I think. The trip to the mall was some diabolical genius on display.
“Are you ready for tonight?” Abby asked.
“What’s happening?” I asked. Abby smirked and took her eyes off the road for a second to look at me. She looked back at the road and put her hand on my knee.
“We’re going to a fundraiser,” she said.
“Oh, where is it?” I asked, realizing why Abby had put in so much effort to make me look good.
“Just in the dorm,” she said. “It’s a cause you’ll feel very compelled to support, too.”
“And what’s that?”
“You’ll see, deary,” she said playfully.
I chuckled to myself, embracing the affection from Abby, eager to please her and a little excited to live a night in public exuding my newfound acceptance of femininity.
We got back to the dorm as it began to get dark outside, early in the evening. Abby parked the car and told me to wait before we got out.
“Now, look,” she said. “The fundraiser just started so just get ready to act the part, OK?”
“OK,” I said. She slipped her hand under my dress and between my legs, digging for the cock that I had buried in my panties.
“I could barely find it,” she said. “It’s like you don’t even have one anymore, Ali.”
I felt the energy I had felt all day while Abby was teasing me.
“Do you think you might be able to finish what we started earlier?” I asked.
“I could,” Abby said. “And if you want me to, I will. A promise is a promise.”
She pulled out my cock and started stroking it slowly. It began to get hard.
“But,” she continued. “Don’t you feel really good right now?”
“Yeah,” I said. “Actually I do. It’s this crazy energy, like being on a drug.”
“Yes, baby,” she said. “That’s it. I’ll tell you the truth and the truth is that the longer you wait, the more intense your orgasm will be when I blow you. Plus, all this pent-up sexual energy might make you more flirty and fun tonight, don’t you think?”
“I can see that,” I said smiling.
“Here’s one more taste to remind you,” Abby said before she lowered her mouth again onto my cock. Looking down and seeing my slutty outfit, my shaved cock sticking out of panties and this gorgeous girl blowing me was the perfect reminder of this crazy experience I was having.
Abby pulled up and kissed me lightly on the lips. She slid her tongue into my mouth, parting my lips. I tasted my own salty precum and remembered the erotic taste of Bo’s that I had last night. It was like a synapse had been formed in my brain that now connected the taste of cum with intense sexual pleasure.
Abby was a mastermind.
“Alright, Ali,” she said. “Let’s go.”
I tucked my cock back into my panties and got out of the car. I had gotten used to walking in the slutty wedges by then and my walk had become a little more feminine because of it.
“Now when we get up there, you’ll see where to go, but we’ll probably get separated,” Abby said.
“OK, well will we talk at all tonight?” I asked.
“I’m sure we will,” she said with a smirk.
We walked into the dorm and the RA on duty leered at both of us. He was a repulsive looking guy in dirty clothes, and he had an unkempt beard. He looked once at Abby, who winked at him, and then looked at me and smiled.
“Ladies,” he said.
“Hi,” I responded in my girliest voice. I guess I had done it automatically to try to fit in as a girl, even though I knew I looked like a tranny.
“See ya later,” he said.
We walked by and got into the elevator.
“Ready?” Abby asked.
“I think so,” I said, unsure of what was to come. Abby pressed the B button in the elevator, which only had the laundry room and a dank storage space. There couldn’t be a school event here. Maybe she just wanted to pick something up.
When the door opened, Abby put her hand on my back and pushed me out. I tripped over my heels and fell on the fround. She stayed in the elevator and waited for it to close. I looked up as she said, “Have fun.”
I stood up and turned to the laundry room where I saw a group of guys hanging out. There were probably about 10 or 12 just standing there. I recognized a lot of them from our dorm floor—the guys in the room next to us, that guy who grabbed his crotch when I was walking past him last night. I started to think this was going to be a repeat of last night times about, well, 10.
“Hey, sugar,” I heard from the laundry room. “Come on over here.”
I walked over to the laundry room from the elevator hesitantly. I didn’t know if I was going to get the shit kicked out of me, or if I was going to get robbed or taken sexually. It was a quick turnaround from the warm, loving day I had had with Abby.
“Ali,” said a familiar voice. It was Bo. “You’re going to help raise some money for your mistress’s tuition.”
“How?” I asked, speaking in a feminine voice. “How am I going to do that?”
A bunch of the guys laughed. The room was filled with the stench of sweat—the unmistakable scent of men. The room itself was poorly lit with one long fluorescent light that flickered on and off. The white tile on the floor was cracked and stained. The washing machines were old, and the boys sat on them.
“Well, these boys all paid 20 bucks to get their dick sucked,” Bo said. “I told ’em you’d get ’em off in two minutes or less or their money back.”
I swallowed deeply. I contemplated running for the door, but where would I be running? Here I was again, caught in a trap I made for myself. My subconscious really must be a sissy.
“But first, you gotta pay for all those pretty clothes your mistress bought for you today,” he said.
“Abby said she would pay for it, or… at least I thought she did,” I said. Bo got up from his chair and stood right in my face.
“Who said?”
“Mistress, sir.”
The boys laughed. I wondered if they were here on their own volition or if Bo had strong-armed them into it. When I noticed a few cocks poking through their shorts, I thought maybe they were all here for me.
“You’ve built up quite a reputation, Ali,” Bo said. “Everyone knows that my roommate is a little sissy bitch who sucks cock and takes dick in his tranny ass better than any of the girls on the floor.”
And now there was officially no turning back, I thought.
“So seeing that you owe your mistress a couple hundred dollars for your outfit, and seeing that you need to start collecting money for her tuition payment,” Bo said, “And seeing that you have this reputation as the fuckdoll to end all fuckdolls… I’m putting your ass on sale for $50.”
The boys in the room started to laugh. I even heard a couple guys slap hands.
“Your two minute time limit still remains,” he said. “Now get the fuck on the floor.”
I did as Bo said and kneeled on the ground. I placed my hands in my lap. My dress rode up a little, revealing my blue satin panties and my stockings.
“Who’s first?” Bo asked.
A short, muscular guy in a wifebeater hopped off the laundry machine and handed Bo a 20 dollar bill. He came up to me and laughed at me. He slapped me across the face.
“Hey, slapping’s another $5,” Bo said.
“I’ll get it to ya,” the muscle guy said. “Let’s see this bitch suck cock.”
He pulled down his pants and revealed a cock about as big as his arm. It sprung to life and I wasted no time in putting it in my mouth, trying to keep under the two minute time limit. The guys started cheering the deeper I got onto his cock. I could feel his dick get even harder and I knew from my own experience that that meant he was about to cum. I was probably sucking him for about a minute before he grabbed the back of my head and pulled me all the way down his cock. I gagged when the tip of his dick reached my throat, and he pulled back the tiniest bit, shooting his warm load directly into my throat. I was breathing through my noise, a trick I’d learned when Bo was throatfucking me the night before, and the sensation of the warm jizz that deep was new. It made me feel like a useless sex toy. All that talk of being a pillar of femininity, a person who chooses to embrace their sexual identity in this new generation that accepts all, was lost. I was just a sex toy for these college guys.
The muscle guy pulled off and I caught my breath. But before I got three breaths in, a fat kid with a tiny dick stepped in front of me.
“Two minutes starts now,” Bo yelled, seeing that I was trying to catch my breath and digest the muscle guy’s cum.
I took a deep breath and got underneath the kid’s belly to his cock. I immediately thought what a fucker this guy is. He can’t take care of his body, and he’s got the smallest dick. He wasn’t a real man. At least I could respect getting taken by a real man.
These are the thoughts of a slut, I realized. As much as I hated what Abby did to me on the surface, the deed was done and my brain had changed into a sissy’s.
I took the fat guy’s whole package in my mouth, tasting his sweaty balls, and he said something dumb like, “Look at this faggot.” He was the faggot, I was the chick everyone wanted to fuck.
“30 seconds,” Bo said.
I started to work double time, sucking this asshole’s cock like I’ve only seen porn stars do. He put his hands on my shoulders and said, “I’m cumming!” excitedly. “I’m doing it!”
It occurred to me that I was probably this guy’s first blowjob.
When he was finished he pulled back, feeling embarrassed. Embarrassed because he had lost his virginity for all intents and purposes to a tranny whore. The other guys laughed at him and he picked up his pants and left. I swallowed his cum and prepared for the next one.
The next guy came up a little hesitantly. I think he was intimidated by me. Why wouldn’t he be? I was looking really put together, had just taken the manhood of one our classmates, and was ready to take it from his. I saw the intimidation I felt for Abby from the other side again.
I reached out and undid his belt when he hesitated for too long. I ripped down his pants and took his skinny cock into my mouth. He immediately made a sigh of pleasure and kept saying “Oh yes.” I worked his cock hard. I realized, this being my fourth cock, which is more than some girls suck in their life, that I liked long, skinny cocks. They had more surface area to taste their manhood, and they were manageable to fit in my mouth. They could also still touch the back of my throat when I wanted to feel used.
Here I was pontificating on the types of cock I liked, on my knees, dressed like a slut in a room full of horny guys. And I felt like I was in control in some weird way.
The guy with the long cock suddenly pulled his junk out of my mouth and squirted his cum all over my pretty face. Bo immediately got up and said, “Hey! No facials!”
The guy chuckled to himself and Bo came over to him.
“That’s 20 more bucks,” he said. And the guy reached into his wallet, pulling out a 20. “And you have to clean her up.”
“What?” he said. “No way.”
“Fucking do it,” Bo said and punched the guy in the stomach. “You don’t cum on her unless you’re told to, bitch.”
“Alright you have a towel?” he asked.
“Use your fucking tongue, asshole,” Bo said.
“Wait, no way,” he said. Bo backhanded him across the face. I was kind of turned on that Bo would stick up for me like that.
The guy got on his knees and started licking the cum off my face with the tip of his tongue. He gathered up a few wads and went to get up to spit it out. Bo put his hand on the guy’s shoulder and said, “Kiss her.”
The guy looked at me, clearly not wanting to get hit again, and put his lips to mine. I opened my mouth to receive his tongue and his warm cum. He worked his tongue in and out of my mouth, getting all the cum in, and when he was done, he ended it with a peck on the lips. He liked it, that little bitch. I swallowed his load and smiled at him.
“Got ourselves a show here, boys,” Bo said. “How ’bout we up the ante here.”
Two guys hopped off a washer as if on queue and one of them gave Bo a crisp $100 bill. One said, “Ready?” to the other like this was some kind of dare. They must’ve been drunk. I didn’t really look at their faces, as I was just focused on their cocks. I still wanted to get them off in two minutes, so when they came over, I took one in my mouth and one my hand. They were already semi-hard and one immediately got as hard as a boner can be. I pulled him out of my mouth and said, “Fuck me,” while looking up at him. He looked like he almost came right there.
The guy moved behind me and I lowered myself onto all fours. I took the slow-riser into my mouth and started bobbing my head and swirling my tongue up and down his cock. I was going to try giving a beautiful blowjob this time. I wanted it to be powerful yet feminine. Playful, yet dominating. A few love nibbles to let him know I’m there.
Then I got rammed in the ass. Feeling that cock enter me was incredible. It straddled that thin line between pleasure and pain, and I started to moan, my mouth full with his friend’s cock.
“Hey Bo,” the guy fucking my ass said. “Where should I cum?”
He was asking my master, not me, where to cum. I guess I owed it to Bo for sticking up for me when the asshole came on my face.
“Cum as deep inside her as you can,” Bo said. “That’ll be nice lube for the next guy.”
The guy behind me grabbed my hips and started fucking me as hard as he could. My satin thong had been pulled to the side and he was pumping deep inside me. My heels wrapped around his waist.
“You ready?” the guy in my mouth said.
“Let’s do it,” the other said.
I first felt a wad of cum shoot onto my tongue. I sucked the head of his penis to get everything out, and kept his load in my mouth while the guy behind me started to orgasm. I felt the hot liquid shoot into my asshole and when I leaned up, some of the first guy’s jizz dribbling down my chin. I scooped it up with my hand and put it back in my mouth. The guy behind me pulled out and the two left the room.
There were four guys left and Bo. I was there on all fours, trying to catch my breath, my belly and ass full of cum. The guys all sat in a row on the washing machines of one side of the room.
“Ali,” Bo said. “If you get all these guys off in five minutes, we’ll let you fuck your mistress.”
“Yes, sir,” I said. I stood up for the first time in a while and wobbled like a bimbo on my heels.
“Pants off, guys,” I said.
“Hold on,” Bo said. “I got an idea.”
Bo went to the corner and pulled out a small table and dragged it to the center of the room.
“On your back,” Bo said to me, and I did as I was told. I lay down and my cock sprung free from my panties, sticking straight up. “Hmm. One second.”
Bo left the room and the guys all circled around me.
“Which one wants want?” I asked.
“I want her mouth,” one guy said.
“What hand do you write with?” one said.
“My right,” I said and he moved over to my right. There was then a scramble for my asshole. Seeing two college guys fight it out to fuck my ass was not something I anticipated liking so much.
Bo came back and with him was a dolled up Abby. She was wearing a lingerie set—baby pink satin bustier with pink ruffle panties and shiny pink latex leggings with heels. Her hair was still pulled back like this morning.
The guys looked at her and one said, “Can I fuck her?” I was immediately put back in my place and felt humiliated.
“No shithead,” Bo said. “You can fuck Ali. This one’s for me.”
“Hi Ali,” Abby said. “You having fun?”
“Yes, mistress,” I said.
“You making a lot of money for me?” she asked.
“Yes, mistress.”
“You ready for that blowjob?”
I was floored. I thought this was all a trick. And now Abby was going to come through with her promise after all. These guys were actually kind of nice. This is all just a big game and I was right about us being in a free-flowing relationship.
“Yes!”
“Well get those guys off and it’s all yours.”
I immediately leaned my head back and took the first guy’s cock in my mouth. Then I reached out with my hands and found the other two guys’ dicks. I lifted up my legs and gurgled, mouth full of dick, “Fuck me hard.”
Getting my throat fucked upside down was a new thrill. Getting fucked on my back was even better. I was pleasuring four guys at once. I had all of their manhood’s in my control at once. What power.
“Three minutes left,” Bo said. I took the cock out of my mouth and looked up to see Abby on her knees blowing Bo’s cock like a professional. I took the guy’s meat back in my mouth and pretended to be as good as Abby was at this.
I let the rhythm of the guy assfucking me take control. There was beauty in getting gangbanged. And I was the main beauty.
“I’m gonna cum,” the guy in mouth said. He shot a load deep into my throat and I swallowed it without any thinking. I pulled the guys I was jerking off toward my head and told them to blast their loads on my face. I could tell they were close so I alternated sucking them from either side.
“One minute left,” Bo said, his hand on the back of Abby’s head like he did to me the night before.
The guy on my left starting to shake so I took him into my mouth and sucked down his warm wad of cum. The guy on my right stuck his dick in my face as I was finishing and shot his load onto my mouth. I tried to put both the dicks in my mouth at once and keep it as clean as I could by eating every drop of cum that came out.
The guy fucking me then bent my legs up as high as they could go and thrust his cock deep into my asshole. He pumped vigorously for 20 seconds and then pulled out. I could feel the jizz drip out of my asshole.
The guys pulled away, laughing, and left the room.
“Nice job, Ali,” Bo said. “You made a couple hundred bucks.”
“Thanks, Ali,” Abby said with Bo’s cock in her mouth.
“You wanna give her what she wants, babe?” Bo asked Abby.
“She earned it didn’t she?”
Abby stood up from her position and came over to the table. She squatted down on her heels and slid my panties to the side. She pulled out my bulging cock and started to suck. It felt incredible.
Bo came over and stuck his massive dick in my mouth from the side. I began to work hard to get him off, thankful for all the money he had helped me raise for Abby, and for keeping me safe from all the other guys. If this is what being dominated felt like, and was like, I think I was in.
Bo’s meat was the best of all the guys I sucked that night. It tasted like a man and it felt like I was doing something kind by sucking him. I flashed my eyes at him. I licked his shaft. I sucked his balls. I deepthroated him. I did everything but look down at the beautiful woman sucking my dick.
I realized this was all part of the plan too. They had now successfully confused my sex drive so that I was more focused on serving than receiving. More interested in cock than in pussy.
That’s why when Bo came, I came. One hand on Abby’s head, the other on Bo’s butt. My mouth on his cock, my dick in Abby’s mouth.
“Don’t swallow,” Bo said.
Abby came up from my crotch and crawled over me on the table. There we were, two sluts in sexy clothes, and now we were swapping cum. We kissed for a while. She sucked up as much as she could and spit it into my mouth. I played the part. I swallowed it all.
“Now,” Abby said. “Any more second thoughts? Any guilt? Any shame?”
I thought about it.
“No,” I said.
“Good girl,” Bo said. Abby kissed me.
“That’s going to make this a lot more fun,” she said.
Sissy Cuck Boy 