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  • A College Sissy Ch. 02

A College Sissy Ch. 02

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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?

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