My Boyfriend is a Better Sister

Carl and I had been dating a few months and things were going pretty well in the beginning but had fizzled of late. At that time, I was a sophomore at USC and he was a junior. We met in microbiology class, became study partners, and then lovers. I couldn't resist his intellect as well as his dimples. Ironically, when people would see us together for the first time, they would ask if we were brother and sister. I was 5'6 and he was 5'8. I had long murky blonde hair and his was short and wavy but almost the same color. I weighed 118 pounds and he was a slender 135. We both loved to work out and stay in shape only I was into running whereas Carl loved to cycle. As you can tell, we had a lot in common but I had feared the romance and passion had disappeared.

I was happy to be living off campus in an apartment but the rent was expensive so I had to take on a roommate. His name was Federico and he was a Hispanic, pudgy, funny, flamboyant, gay guy who was so fun-loving and kind. When my friends came over, he was just "one of the girls" who made us laugh uncontrollably. He would snap his fingers, talk effeminate, and say all the cliché phrases like, "You go girl" and "Talk to the hand," and he either said, "Child" or "Girlfriend," before most sentences. He was just fun to be around.

When Carl would come over, he wasn't a fan of Federico. I don't think he disliked him but Federico's flamboyant style wasn't his "cup of tea." Carl would just roll his eyes and basically try to act like he was interested in conversation with him. Carl knew I considered Federico a very good friend so he learned to coexist when we were all together at the apartment. Carl's attitude toward Federico was just another reason our relationship was coming closer to an end.

Carl had no classes on Fridays so he would always sleep over with me on Thursday nights. I had an 8am on those days so I would get up, shower, go to class, go work out with my girlfriend Maggie, then we would grab lunch together while Carl waited for me to return. Federico went to his boyfriend's place at that time. I kept that routine for many weeks. Once I got back, I would shower again and then Carl and I would spend the rest of the day together.

It was getting close to Christmas and on that particular Friday, Maggie was going Christmas shopping with her mom so after class I decided to head back to my place. I opened the door, sat my things on the counter and headed back to my bedroom, fully expecting Carl to be asleep.

When I opened the door, I was shocked to see Carl as I yelled, "What are you doing?"

He was obviously more surprised to see me back that early as he jumped a mile and even dropped my dildo on the floor. Let me describe what I saw. Carl was sitting on the edge of my bed, dressed up in my clothing, sucking on one of my large dildos from the "toy box" in my closet. He was wearing my pink sweater along with a white miniskirt and my black Charlotte Russe high heels with the straps that came up around the ankles which were too small for him. While dressed like a girl, he was sucking on my real-feel 8 inch rubber dildo with his hand inside the skirt, jerking his own cock.

He was absolutely mortified as neither of us spoke for a good ten seconds before he finally attempted to offer some sort of failed explanation, "Uh...well...um...I was just...just..."

I was still in shock and Carl put his head down and mumbled, "I really don't know what I'm doing. I just get these feelings I can't explain. Why are you back so soon, anyway?"

I sat down on the edge of the bed beside him and asked, "Feelings? What do you mean?"

He looked up with his puppy dog eyes, "Well, I just get so turned on thinking about dressing like this. I don't...don't know what's wrong with me."

I suggested, "Maybe you are gay."

He quickly interjected, "No...no I'm not. I find girls attractive. I just don't want to break up over this. Please, I won't do it anymore."

I shook my head, "I don't think we can stay together and not just because of this."

He begged, "Oh please. Don't do this. I said I wouldn't do it anymore. I will do anything if we can stay together. I love you so much."

"But you were deepthroating that dildo when I walked in. You obviously want to suck cock. You need to find out if you are gay or not," I recommended.

He agreed, "I do think about what it would be like to suck a cock but I think it is just a fantasy. Believe me, I like girls and you are the girl I want. Please don't break up with me."

It was difficult to take him seriously while he was dressed in my clothing but I was listening. The more I thought about it, the more it played to my fantasy. I was getting aroused, not because my boyfriend was crossdressing but because it opened up my fetish to control a guy. I didn't mean control in a mean spirited way but in a nurturing sexual humiliation kind of way. I realized how much fun this could be and I was not going to miss that opportunity.

"We won't break up if after this weekend, you feel the same way. You have been secretly dressing up as a girl so this weekend, you will be a girl. You will be a girlfriend of mine or better yet, my sister and do everything I say to do without question. You say you are not gay but I say you don't know that until you have experimented. Can you agree to these terms?" I explained before asking.

He was reluctant but agreed, "OK, but after this weekend, can we go back to the way it was before?"

I answered, "Sure. If after this weekend, you have the same feelings about our relationship, we can continue to give it a try. I'm not joking either. You have to do everything I ask you to do without questioning it, no matter what it is."

Carl sighed in relief while nodding his head, "I can do that for a couple of days I guess."

"The first thing we need to do is to see if you enjoy sucking a dick for real," I said as I began texting.

He fidgeted nervously while asking, "I don't know about that. Who are you texting?"

I smiled, "You said anything I say, you would do, so we are doing this. I texted Federico and he will be coming home in a little while and we will see how good a blowjob you can give. You also will stay dressed in my clothes. Oh and by the way, this weekend, your name is no longer Carl. It is Carla."

We sat in the living room and after about 30 minutes, Federico walked in. As soon as he saw Carl dressed in my clothes, his eyes widened while shaking his head back and forth and waving his arm up high, "Child, I knew it. He wants to be one of us."

I explained to Federico in my own way with a subtle wink, "I want you to meet my sister Carla. She is from out of town and wanted to meet you. She wants to suck your cock and I think you should let her. Don't you?"

When Carl wasn't around, Federico would tell me how cute he thought Carl was. Federico just looked at Carl then back at me then back at him before it dawned on him, "Oh...OK then. Girlfriend, let's do this after I go wash my junk. When you called, I was bare backing Julio so it might be a little dirty."

I quickly spoke for Carl, "Oh, that's OK. Carla likes it dirty. She is ready now."

Federico weighed about 235 pounds but was only 5'7 and because of his weight, he frequently wore long khaki shorts. He unbuttoned and took them off along with his boxers. He sat down on the couch with a large smile on his face.

Carl was hesitant and just stood there until I nudged him, "Go on sweetie. Let's see what ya got. I will be here for you and teach you all you need to know." I handed him a large pillow, "Take this for your knees."

Carl took the pillow and placed it between Federico's feet. He was moving at a snail's pace because of his indecisiveness but he also knew he had no choice if he wanted to be with me. Federico's cock was flaccid and hung down over his resting balls.

Once Carl was situated, he froze until I offered encouragement, "Go on Carla. Take it in your mouth. You have to get him hard."

Carl leaned down and took Federico's penis into his mouth. He started sucking while Federico's smile became even wider. Within seconds the estimated six and half inch cock was fully engorged.

I sat on the couch next to Federico and began instructing Carl, "That's it. You got him hard very quickly. Now Carla, be sure you don't let your teeth scrape. No guy wants that. Keep your lips across your teeth then make a suction with your mouth like a vacuum. That's better. How does that feel Federico?"

Federico giggled, "Child, I couldn't do better myself."

I continued with Carl, "You can use your hand in the beginning, so go ahead and jerk it a little while you suck. But remember, when you're giving a blowjob, guys want to be sucked off, not jerked off."

Carl's head was bobbing up and down with Federico now moaning softly at me, "He's gonna make me cum very soon."

I giggled his correction, "You mean SHE is gonna make you cum." Then I focused back on Carl, "Did you hear that Carla? You are doing great. You are going to make him cum for you."

Carl hummed back at me the best he could with a mouth full of dick, "Umm hum."

I continued my blowjob lesson to Carl, "Keep a consistent pressure and friction with your mouth. You can use your tongue. It is OK to stop and edge him before going back at it."

I found myself getting wet from not only seeing my boyfriend suck cock, but even more so from coaching him. He was doing a nice job and I could tell he was a natural even though there was a big difference from getting a blowjob as opposed to giving one.

"The girls who give the best blowjobs show enthusiasm. We want and love to suck cock and I think you are showing that Carla. Good for you. Look for subtle clues from the guy you're sucking. Is he moaning? Is he shifting around in his seat? Can you feel his cock throb in your mouth? Those cues will tell you how good a job you're doing and if he is close to cumming," I continued to coach.

Federico interrupted with a shiver, "Yes to all the above."

I giggled as I continued, "Don't be afraid to deepthroat him. You know from experience that guys like that. Remember when he cums, don't slow down or stop. Keep that constant rhythm until he is completely finished."

Carl continued sliding his mouth on Federico's dick with loud slurping sucks. I knew Federico was getting close and it was only a matter of time. Carl also listened to my instructions as I now noticed when he would go down, his lips would press into Federico's pubic hair which meant he was deepthroating it.

Federico's upper body began to heave as his back arched before grunting, "Oh! Oh! Yeah, I'm cummin! I'm cummin! Aughhhh! Augghhh!"

To make sure Carl didn't change his mind, I leaned forward and placed my hand on the back of his head while advising, "Stay with it. Don't slow down. Suck the cum out of it. There you go...suck it out. Don't stop until it stops shooting. Let him finish...let him finish."

When Federico stopped cumming, his tensed up body, returned to its relaxed state as he sang, "That was amaaazing! Carl or Carla, whoever the hell he is, can suck my dick anytime. Wow! I needed that after you girls interrupted me with my hunky man. Now if you would excuse me, I need to get back to him."

Carl looked at me with a closed mouth full spunk when I commanded, "Swallow it down. Go on. A good blowjob giver and good slut never spit. Down the hatch."

He closed his eyes, swallowed the mouth full of sperm and then winced pretending to be disgusted. I knew better judging by his hard-on tenting out the front of my skirt that he was wearing, not to mention, the huge wet precum spot on it.

Federico had already dressed and left when Carl asked me, "I did it. Can we get back to normal now?"

I chuckled, "Sure sweetie. Come Monday morning we can as long as you listen the rest of the weekend."

"Can we have sex now?" He inquired.

I chuckled again, "Uh, no I don't think so. You need to get my skirt off before you ruin it with your leakage. You can keep my high heels on and go jerk yourself off in the bathroom. It won't take you but a minute." I handed him a box of tissues, "Use these so you don't waste toilet paper."

Carl shuffled and clicked his high heel covered feet across the floor until he entered the bathroom. Within minutes, I heard the faint, echoed grunt of his orgasm. When he emerged, he was naked except a towel around his waist. My folded clothing was in one hand, and the straps of my high heels were tangling from his fingers in the other.

For that weekend, Carl was my slutty sister and not my lover so I needed him to leave. I was extremely horny from what had just taken place. I directed him, "You need to go back to your place now but I will need you back in a couple of hours. We need to get you prepared for tomorrow."

Carl tried to argue but in the end, he left. My pussy was wet and I immediately called my ex-boyfriend whom I dated before Carl. Hunter and I never had much in common except for sex. He was well hung with a thick 8 inch manhood and I needed it inside me.

Hunter was busy, so it took him an hour to make it over and was really surprised by my call after such a messy breakup. We exchanged pleasantries and ended up in my bed. Thank goodness I still had a few of his XL condoms in my top drawer from when we dated. I had missed that large dick and feeling it slam into me again made everything right with the world. We fucked in every position imaginable and I lost track of my orgasms. He had already fouled one rubber with his hefty load and was working on number two.

We were both sweaty after making love for so long. I lost track of time when Carl had returned. When he walked in and saw me riding Hunter's big dick and angrily spouted, "What the hell, Britt? I thought we were staying together? I leave and you immediately fuck somebody else and of all people...him?"

I continued bouncing on Hunter's cock when I answered Carl, "We are after Sunday. Remember, this weekend we are not together. You are my sister. After seeing you give that blowjob, I was so horny. Could you close the door please? I will be done in a little while. You can watch TV out in living room if you want."

When the embarrassed Carl closed the door, Hunter gave me a puzzled look and I informed him, "It's a long story. We probably need to hurry up. You can go ahead and cum again."

Hunter lifted me up and laid me onto my back before placing my legs behind my head and forcefully fucked me like a train. I screamed moments before Hunter growled while filling up his second condom. When he was finished, I removed the slimy rubber from him and sent him on his way.

As Hunter was leaving, I told him, "Thanks baby...that was amazing. Don't call me though."

Immediately, Carl entered the bedroom all distressed when I reassured him, "Calm down. That is no big deal. I was so worked up from you blowing Federico, I needed my own relief. It was just sex and that was all."

Carl wasn't pleased but he did calm down. He knew he had no choice and if he wanted us to stay together, he would have to submit to my every wish. Before you think, "Poor Carl," I saw that he was once again, supporting a huge erection in his pants that was very noticeable. I believe he was emotionally torn by our situation but couldn't control his arousal.

"I saved these for ya," I said to Carl while holding up both used condoms left by Hunter.

Before he had a chance to balk, I snapped at him, "Please tell me you aren't going to resist everything. We made an agreement and you need to honor it. You already swallowed a mouth full of cum so this will be no big deal. This weekend you are a slutty girl and will be treated as such. Now come over here and drink the cum from these rubbers."

Carl sat down on the bed as I stood up beside him. I had him tilt his head back and open his mouth. I carefully turned the full condom upside down and slid my fingers down the length like I was trying to get toothpaste out of the tube. The bubbly, slimy, liquid plopped into his mouth and he swallowed. I then repeated that routine with the second used rubber.

Once the spunk had been deposited in his stomach, I reassured him, "See, that wasn't so bad. As soon as I get dressed we can get started on preparing you for tomorrow."

My plans were simple. I was going to dress Carl up for Saturday night and pass him off as a girl. I didn't want him to look like a drag queen but a legitimate female. He was petite and I believed I could pull it off. I wasn't going to half-ass it but pay attention to all the details. I wanted to see if we could get "her" a date with a guy without the guy knowing. Before we were to do that, on Saturday morning, we were going shopping for a sexy outfit and have a spa preparation afternoon.

Luckily, Carl was mostly hairless except for his legs, armpits and a little on his forearms. I had him take a warm bath before I shaved his legs and armpits for him. I didn't want him to cut himself all up so I needed to use my experience to get the job done. While in the tub, I had him turn over to make sure his asshole was also hairless and after a few razor swipes, it was. I would wait for the next day to shave his face even though he didn't grow facial hair very well.

We watched a movie and he stayed all night with me but slept on the couch. When the morning arrived, I got him up and he started to get dressed before I stopped him, "Wait! What are you doing?"

"Getting dressed," Carl responded.

Those aren't your clothes to wear today. You are Carla all day and you need to dress appropriately. Come in my room, I have some leggings for you to wear with a cute top to match," I informed him.

He had finally stopped resisting and put on the tight black leggings with the top. I could tell he was embarrassed but he was the one who started all of it by crossdressing while I was away. Since my shoes were too small for him, I borrowed a pair of slip-ons from Federico and Carla's outfit was complete. I handed him a pair of nude knee high nylons for his feet so would be able to try on shoes at the mall very quickly without socks intervening and it's rude to wear other people's shoes with your bare feet. I threw on some leggings, a t-shirt and my tennis shoes. We were just two sisters heading out.

Our first stop was at the nail salon. We were in southern California, so Carl wearing leggings wasn't a total shock but when I asked them to give us matching colors on our fingers and toes, it was. While I was getting my manicure, Carl was getting his pedicure and vice versa. I did notice a couple of younger girls snickering at the counter. When finished, we both had beautiful shiny maroon nails and after he put his hose back on, I allowed Carl to pay for it.

We headed to the mall and Carl asked while in the car, "What if I see people who know me?"

I smiled, "I guess you should have thought about that before sneaking around and jacking off with my clothes on."

We walked in the main doors and first store we entered was Victoria Secret. It was crowded with women and girls all around, looking at the items. As I held up a lacy black and red silk crotchless panty and bra set, I asked Carl aloud, "Do you think these will fit you?" When several of the girls looked up, Carl wanted to crawl underneath the table from embarrassment but I continued, "Oh yes, I think they are your size. They will look sexy on you."

After we picked up some black stockings, we checked out and headed to the shoe store. As we walked in the mall, I instructed Carl, "You need to do some of the talking in this store. I want you to try on at least two pairs of high heels and walk around, asking the helping employee some questions.

Once inside, the clerk asked, "May I help you?"

When I nudged Carl with my elbow, he responded, "Uh...yes...we need to see your high heels."