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by fun4all6969 (edited)
My brother Josh and I are both kind very shy and one year apart in age. My brother is five feet ten inches, a little muscular and manlier than me at twenty. I am eighteen, five feet six inches, one hundred and twenty pounds, with a three-inch pencil thin cock and tiny balls to match. Despite going through puberty, my body is still hairless. In the last year I started developing small breasts on my very petite body. My doctor told me I have low levels of testosterone in my body, and high levels of female hormones that has caused me to develop female attributes.
I have always been into dressing up in my Mom’s and sister’s clothes whenever no one is home. Melissa is my fraternal twin, shy like us, but sexy. She is five feet eight inches, one hundred and thirty pounds, pleasantly curved, and has small pert breasts.
Our Mom and her boyfriend left for their annual three week summer trip to Mexico. The first night we were watching some soft core porn on cable and drinking some alcohol together. We got to talking about girls, and Josh confessed, “Bro, I really need to be with a girl, but I’m so nervous since I have no experience and never kissed one.”
I was more than a little drunk, and blurted out, “I’d be willing to put on some of our sister’s clothes and let you make out with me for practice.”
He looked at me like I was a freak and I started to say I was sorry, but he stopped me and told me that might work. “Dude, you would do that for me?”
“Sure bro… Because I love you. I’ll be right back.”
I rushed upstairs, knowing exactly what clothes I would put on because I had done it before. I decided to raid Melissa’s room first. I stripped down, dropping my clothes. It was erotic to be in here naked. Opening her underwear drawer, I found a pair of frilly pink thong panties. I slid them up my thighs, feeling the odd sensation of silk around my cock, which was growing erect against the fabric. I put her bra on my chest. It was a little big for me, but it pulled my breasts together and made me look quite sexy.
Next I went into Mom’s room and found her thigh-highs. I slid them up my legs, and then over the top of it, I added a miniskirt and a camisole which made me have curves and fit snugly around my hips. Leather thigh high boots and a blonde wig completed the effect and I thought I looked great.
I wobbled my way downstairs on the heels and Josh turned, and said, “Wow, you turn into a very sexy woman.”
I blushed and sat down next to him. Josh was intoxicated and horny, and it was like he forgot who I was. He grabbed my face and started kissing me very sloppily, with his tongue deep in my mouth. He was groping my breasts and it was really turning me on. I felt his hand grab mine and direct it towards the bulge in his pants and I don’t know why, but I let him. His cock felt huge as I traced it with my fingers. It had to be four times thicker and maybe three times longer than mine. He moaned into my mouth as he guided my hand into his shorts.
I gasped as I felt that thick cock in my hand and started stroking it. I disengaged from his kiss and leaned down like I saw in the videos and kissed his cock as he slipped off his shorts. I sucked and licked his cock, and it wasn’t long before he grabbed my head as I felt him spasm in my mouth. I tried to move off, but he held my head down as he came and I could do nothing but swallow. As I licked him clean he groaned, and said, “Oh my god, that was the best thing I have ever felt.”
Josh went up to bed and I peeled off the boots and Melissa’s clothes. I put away the clothes and went to bed and jerked off.
I woke up the next morning and Josh had already gone to the gym. I remembered the feeling I had wearing panties, so I dressed, putting on panties under my pants and went out for a drive. As I was driving I noticed an adult bookstore and went in slowly as I was nervous. I was overwhelmed with all the videos, toys and clothes. I started walking around and noticed these shemale and transvestite videos. Wow, I thought, this is what Josh and I did last night. A stud with a big cock and a tiny cock shemale.
I grabbed a couple, not knowing if I could go through with buying them. When I looked towards the counter there was this incredibly hot twenty something year old girl. I slowly walked toward the counter and the girl smiled, and said, “Hey, don’t be worried, we don’t care what you buy as long as you buy.”
We chatted for a few minutes, and she looked at me, and said, “Do you like being the girl?”
I blushed and nodded my head yes. “I have the perfect small breasts to go with it,” I said.
“You have a great build for it. Hey, my name is Kara.”
“Nice to meet you.”
“You should have fun with these videos. Do you have any experiences while dressed?”
“Well, actually, now that you ask… I dressed up last night and sucked my brother’s large cock.”
“Wow! Well, if you do that again, here is my number. I want to watch,” she said, handing me a card.
I went home and cleaned up and decided to have a movie set up and be all dressed when Josh got home. I put on the same outfit as last night except with some heels instead of boots and was sipping a drink when he walked in. He just set down his stuff and rushed over and kissed me. I handed him a drink and told him about the girl at the video store. He was nervous, but said to give her a call. He went up to shower while I called and she said she was getting off work in fifteen minutes and would head right over.
It was not long before she arrived. I opened the door and let her in. Seeing me, she let out a long whistle. “You are even sexier than your sister. I graduated two years ahead of her. You know, I’m going to use this to my advantage and you will both be my slaves and do whatever I want, or I may need to tell your sister or Mom about this.”
We agreed. What could we do?
“Ok, first, I want to see how the two of you make out. Show me your best kiss.”
With that command Josh leaned over and started kissing gently at first and then pushing his tongue deep in my throat. In the meantime, she popped in one of the DVD’s and noticed Josh’s cock straining. She then said, “Sissy, that big cock of your brothers needs taken care of.”
I lowered myself down as he slipped out of his shorts. She continued, “Wow, that is a nice size cock” as I devoured it. Kara stopped me and said “Josh, take a look at the video.” We noticed the stud was sucking the small cock of the shemale. “Do what they do. Get down there and suck Sissy’s clit.”
Josh started to protest, but she became more forceful. “You want to make me happy don’t you because if you do, I might be willing to try out that big cock myself?”
That convinced him. He leaned forward and pulled my little cock free. Kara gasped again as she said, “I can see why you are the sissy, because that is the smallest cock I have ever seen.”
I knew I wouldn’t last long and Josh pulled back just as my cock spasmed and out dribbled a tiny bit of cum.
Josh quickly grabbed his drink as Kara gave me her next order. “Sissy, go get some lube.”
I went upstairs to our Mom’s room and found her lube and came back down. She then said, “Josh, I want to see you fuck Sissy like a girl in the missionary position and I want you to kiss her while fucking. Make sure Sissy’s ass is well lubed.”
When she said it was time he moved forward with his cock. It really hurt at first and he went slowly until he was all the way in. As he started thrusting harder and faster, I felt really turned on. He was kissing me hard while thrusting with his tongue going in and out of my mouth. He lasted about 10 minutes and as he got close Kara said, “Make sure to cum in her just like you would a girl.”
With that, Josh grunted and I felt his cock spasm and a warm rush inside me.
As Josh slid out, Kara told him to go shower and come back down. She asked me to get us a drink and we sat down. She leaned forward and kissed me and I couldn’t believe a girl was kissing me and thrusting her tongue in my mouth. Kara pulled away, felt my panties, and said, “I see you liked that. Please take off your top and bra, I want to see those breasts. I did, and she continued, “Wow, you’re growing some small ones there.”
I confessed to her that somehow I have more female hormones than male ones. She admitted that seeing me dressed and knowing I was a shemale in real life turned her on. She then said, “I hope this doesn’t bother you, but I’m going to fuck your brother. He may not be the most handsome man, but that huge cock gets me wet. I would let you fuck me, but I’m afraid that little dickie would do nothing for either of us. I will offer a compromise, when your brother is fucking me doggy style you slide under and lick him and me and for that I will give you a blow job.”
I couldn’t believe it and agreed really fast and she said great, just play along.
As Josh came down, still naked, and he saw me topless and noticed my little boobs. He said, “Bro, I mean, Sissy, what are those?”
I explained and I noticed his cock rising. At that moment, Kara stood up and pulled off her top revealing perfect B cup breasts and slid down her shorts and pointed out her huge wet spot on her panties. She said, “Look what the two of you did to me,” as she peeled them off, revealing a very hairy pussy with wet matted hair. She said, “Sissy, you can lick my pussy juice off my panties and Josh you can lick me right here,” as she pointed at her pussy.
Josh dove right in and Kara was directing his tongue action with authority. As I was licking and savouring her panties, Kara had an orgasm and squirted on Josh’s face. He was a little freaked out and she said, “Don’t worry, because this is what happens when you do a real good job.”
She then kissed Josh and licked his face clean. She pushed Josh back and slid her wet hairy pussy right on Josh’s cock. Josh moaned out in disbelief as she pounded up and down on his cock. She said, “Sissy, get over here and lick your brother’s balls.”
I leaned in with my nose in her ass and tongue on his balls. She pulled herself off and got into doggy style position. She directed Josh up behind her and then she motioned to me. I slid under her and started licking Josh’s shaft and her clit while I felt her pull my cock out of my panties. I felt her mouth slide over it and I couldn’t believe how good it felt. She stopped and told me to keep licking and within 5 minutes Josh grunted and I felt his cock spasm as I licked his balls. As he slipped out Kara ordered me to lick his cock clean and then suck his cum out of her.
I greedily licked her pussy and sucked out his cum and right after her orgasm she started sucking my little cock again. I came in under 20 seconds and she swallowed and said, “That is the least amount of cum I have ever had from a blowjob. Remember that you both are mine now. The two of you are allowed to do things together, but anything else is off-limits unless I ok it.
Josh and I both went upstairs exhausted as Kara went home. I woke up to my phone ringing and it was Kara. She said, “I work the day shift today, but I have plans for the two of you tonight.” Kara arrived at five pm and she had brought over some clothes. She had me put on my sister’s bra, a sexy top, thong panties, short black skirt and black leather boots. She did my makeup using some from my Mom’s bathroom and I looked in the mirror and thought, wow, I am hot. Just then Josh came home and walked in to see me, I saw his cock stiffen. Kara grinned, and said “Down boy, we’ll save that for later.”
We jumped into Kara’s car for my first public trip dressed as a girl and it felt good. We went to an adult bookstore nearby the one Kara worked at but this one looked sleazier. We paid and headed to the theatre and as my eyes adjusted I noticed there were about ten guys here with Kara and me being the only girls. Kara said, “My friend Sissy here is willing to suck all of your cocks. My guy friend and I will put on a show fucking for you, but no one touches either of us.”
The men all looked pleased with this arrangement. Kara turned to me, and said, “Sissy, this is your big chance to show me you’re a true girl.”
I licked my lips and sank to my knees in front of the first guy. His cock was smaller than Josh’s but still plenty big. I managed to deep throat him and he came right away. The second and third guys pulled out and covered my face in cum. I licked my lips and moved on. Around the seventh, I felt somebody playing with my ass. It felt like a girl’s hand and touch and I felt lube. Kara then announced that the first guy with a condom would get to fuck me. The guy in my mouth pulled out quickly and on went a condom on his cock.
He pushed in easily and pounded away while a guy replaced him in my mouth. I felt the guy in my ass pull out and I saw him peeling off the condom to cover my face as the guy I was sucking filled my mouth. I felt another guy enter my ass and he didn’t last long and filled his condom in my ass. He pulled out and Kara ordered him to pour that cum all over my face.
Josh helped me up and Kara took a couple of pictures of my slutty cum covered face. I wiped some off, but there was so much I gave up and we just walked out of the store. As we drove home Kara asked me, “Did you enjoy being a slut?”
I smiled big, as I said, “That was the best night ever.”