My girlfriends younger brother by Freethought32@yahoo.com
This story involves teenage crossdressing and sex. Only read if you of age and like this type of material.
It is purely fictional. I hope you enjoy.
My name is Mark and I have been dating my current girlfriend, Beth, for about a year now. We began our dating in freshman year of college when we met in a sociology class and hit it off real well. We get along great and I have no complaints. Well, no major ones except that she is pretty fundamental when it comes to sex. She is old fashioned and believes in not going all the way until marriage. I can respect that it's just that I do not have those same beliefs and it makes it rather difficult at times. I don't pressure her and don't ever plan to. I get an occasional handjob from her, she says to keep me happy. But it doesn't always do the job. I have never cheated on her, though at times I can honestly say the thought crossed my mind. I know I would feel lousy but there are days I almost stray. This brings me to the story at hand. She still lives at her parents with her mom and dad and brother. The parents are real nice but I never got to know her brother Eric real well. He just turned 18 and is a quiet guy that is always polite but doesn't have much to say usually. Beth and I went over there for one Saturday to help her do some housework, mom and dad were to be away at a friends house and we were supposed to be all alone. When we got there we noticed that was not the case. Eric, who was supposed to be at his friends house, was at home instead. No big deal, not like anything was going to happen. He seemed surprised, though, that we were there. We heard him close his door upstairs quickly as we entered the house. She called to him and he said he would be right down and moments later he came down the stairs.
"Hello Mark, hi sis. What's going on? I didn't expect to see you two today." Says Eric.
"Well, I have some work to do around the house that mom is bugging me to do so I figured while they were gone I would take care of it." Says Beth.
"Oh, ok. Anything I can help with?" Says Eric
"Nah, Mark and I got it." Says Beth
"Ok, call if you need me." With that Eric heads back up the stairs.
Just out of reflex, I turned to watch him make his way up as Beth and I headed to the kitchen to start on some cleaning. I did a double take, literally. At first I wasn't sure but on a second look I was positive. Eric had on some shorts made from cut off sweats and as he walked up the stairs I distinctly noticed a panty line. I can say I know for sure because I am an avid ass watcher. That is my favorite part of the body and I love visible panty lines, that just turns me on. That's how I knew, without a doubt, he was wearing panties. I was shocked at first, kind of confused, but I am an open minded person and figured if he likes it, that's cool. As the day went on, and we did her work, I kept thinking about what I saw. It was taking up much of my thoughts and I wasn't sure why. I always thought of myself as a straight guy but for some reason the sight of his nice, yes now I was thinking of it as nice, butt in those sweats and panties. And I was getting really turned on from it. As it was nearing dinner, Beth decided to cook Eric and I some dinner but she had to go to the store first. I let her take my car and said I would just chill by the tv while she was gone. Although I had other ideas in mind to kill the time, like go talk to Eric. The trip to the store and back would take about hour at this time of day with traffic, plus shopping, I figured I had about an hour and a half at least until she returned. I watched her pull away and went into the kitchen to get a Pepsi. As I walked by the stairs I yelled up for Eric.
"Hey Eric, come on down and have a Pepsi with me. Beth is gone to the store and I'm bored." I said.
"Uh, ok. Sure." He replied and came down into the kitchen.
He had on the shorts still but I can tell he changed the underwear.
"So tell me Eric, what's new with you? Anything fun and exciting happening in your life?" I said.
"No not really. Just checking out colleges and stuff. Nothing great." He answered.
I engaged in small talk with him as we sat at the kitchen table for about 15 minutes, trying to get the nerve and find the right way to ask him about what I saw earlier. I finally decided to quit wasting time and get to it.
"Those are some cool shorts you are wearing. I have a couple pair like that myself, real comfortable I think." I said.
"Yes, I like them. They fit well and like you said, are comfortable." He answered.
"To tell the truth, I especially liked them on you when we got here earlier."
He looked at me, a little nervously but not outright showing it and said, "What? What do you mean?"
"Listen dude, I know you were wearing panties earlier. I can tell very easily. I saw them on you as you went upstairs, when you were shocked that we were here. Did you think you would be all alone and didn't have time to take them off?" I said, getting a little nervous myself.
He sat with his mouth slightly open, unsure what to so I continued on. " Don't sweat it, I won't tell anyone. Honest. Truthfully I liked it. I never thought I would say that about such a sight but you looked fine from what I saw."
He got a little red, probably ashamed that he got caught. "Please Mark, please don't tell anyone. I would just die!"
"Don't worry, I won't. But for me to keep quiet I want you to go get dressed for me right now and we will talk." He sat for a couple minutes not really knowing what to do. Slowly he got up and went to his room. I was so nervous now and waited anxiously for him to come back. It took about 15 minutes for him to return and I must say I was surprised. He was in a black skirt, not really a mini skirt but it was above the knee, and a white half shirt. The attire looked familiar, it was some of Beths old stuff except he had cut the shirt to his liking.
"Damn, you look fine!" I exclaimed which made him blush again. And I couldn't believe I said that about a guy dressed as a girl but he was cute looking. "What are you wearing under that gear?"
Quietly with his head down, "Blue bra and panties."
"Let me see!" I said inching forward in my chair.
He raised his shirt up a little showing his bra and then did the same with the skirt showing his panties. He was so adorable.
"Here, sit, and let's chat" I said holding out a chair, which he sat in.
"So what's your name sweetie?" I asked.
"Uh, Brooke" He shyly answered.
"Brooke is it. You been doing this long?"
"A couple years now, been taking things that my sister has been donating to the Salvation Army and keeping them for myself and hiding them away."
"Why do you do it?"
"I don't really know, I just like it."
He looked so submissive and shy. And very cute. Was talking very quietly which sounded nice and with his hair style, which wasn't long but I guess he knew how to make it look feminine, looked very much like a young girl. And I was getting very turned on. I knew time was running out and who knew if I would get this chance ever again so I got up and went to him. Reaching out and taking him by the hand, I coaxed him to stand.
Looking into his, no her eyes, I said, "Brooke, I never considered myself anything but straight. However, seeing you like this, standing near you I feel I must do something." With that I pulled her close and kissed her fully on the lips. She was shocked at first but gave into it eventually and we kissed, mixing tongues, for a few moments. It was one of the best kisses I had ever had. I broke it off and stared down at her briefly before kissing her again, this time I let my hands roam to the object that caught my original attention, her butt. I felt up her ass first over the skirt, then by reaching under it, all the while kissing her passionately. It felt great, natural. She was moaning which led me to believe she was enjoying it as well.
"Let's go to your room Brooke," I said as I led her towards the stairs allowing her to go first. I wanted to see that ass again. She hesitated slightly then went up but at the nest to the top step I stopped her and told her to reach forward. This made her bend at the hips jutting out her ass. I got up behind her, lifted her skirt, and saw her ass in those panties for the first time. Gorgeously smooth and soft. So much so I leaned forward and kissed it right there, over and over. She seemed to like that but there was much to do so we continued on to her room.
We entered her room and kissed again for a few moments then I said softly, "You are lovely my dear Brooke. I wish we had more time but your sister will return in a little while and there is so much I think we both want to do." With that I gently pushed her to her knees. I didn't have to force it. As soon as she noticed what I wanted, she went down on her own. She lightly kissed my crotch through my jeans at the same time felt my butt, I was so hard by now and she knew it. She unzipped my pants and pulled out my cock. It isn't huge, almost 7", but it does the job. She began stroking it and licking it. I don't think she ever did this before but was sure what to do. After a little of that she took it in her mouth and I had to grab a hold of her head. It had been a while since I have had a mouth on my cock and I didn't want to cum too quickly. I watched as her pretty head bobbed up and down on my cock in a good rhythm as I thought to myself, "I can't believe I am having my girlfriends brother, dressed as a girl, sucking me off. And enjoying it!"
I had only intended on getting a blowjob but ideas began circulating in my head. I kept thinking back to that ass and how much I wanted it. No, had to have it. With some regret I stopped her from sucking me and raised her up.
"Sweetie, you give some great head but it is time for you to get something in return. From the moment I got here you butt has been on my mind and now it is time for me to have some of it."
"I...I'm not sure."
"You'll like it hon., I promise. Besides hotties like you are meant to get some sex, wouldn't you say?"
"You think I'm a hottie?????"
"Oh yeah, definitely!"
She seemed to like that a lot judging by the smile on her face. I led her to the bed and got her up on all fours. Getting up behind her I cradled her ass in my hands and massaged her cheeks real good. She started moaning again and I could tell she will like this. I flipped up her skirt and pulled down her panties to reveal her fine ass. With no lube, I used saliva soaked fingers to loosen her up some. One by one I got three fingers in her and she moaned louder every time. Then the time arrived. I quickly got my pants down to my knees and went to it. I grabbed a hold of her hips and moved my cock into place. Slowly I eased into her ass reveling in how tight she was. Inch by inch I slid into her letting her get used to it every time so as to not cause too much discomfort. When finally I was all the way in and she was ready, I began fucking her. I built a slow but steady pace to get used to her but then I went at it fully slamming into her virgin ass as she moaned and cried out.
"Oooooh Brooke, you are such a good lay!!! You have such a sweet ass!!!!"
"Yes, yesssss, fuck me, fuck me hard!!"
"You better believe you'll get it hard baby girl. You're my girl now right!?!"
"Yes Mark Yes, I'm your girl to do with as you please!!!!!! Fuck oh yes, fuck me good!!!"
All the sexual pressure I had been feeling was building up into one hell of an orgasm and Brooke here was going to take it all. We moved onto the floor because her sheets were sliding and causing a problem. But we continued down there harder than before. I knew I wasn't going to last much longer. Just watching my cock go in and out of this gorgeous ass, knowing who she was, was enough to just about send me over the edge. When somehow she heard the door open and shut. She stopped us right away and we listened.
"Mark??? Mark??? Where are you at? Eric???" Beth, who had just returned, called out from the living room.
Scared I didn't know what to do. Here I am with my cock buried in her brother's ass, he dressed as a girl, and my girlfriend just came home and was calling for me. I collected my breath.
"Beth, we're up here. He needed some help with his computer so I am lending a hand." I said. She always encouraged us to get to know each other better so this was a good excuse to be up here.
"Ok, that's fine. I just got back and will start dinner soon so don't be too much longer." She replied and I heard her go into the kitchen.
With a sigh of relief, I remembered what was happening. I leaned down next to Brooke's ear, "Ready to finish? Just be quiet and all will be fine" With that I began pumping away again into her ass. Somehow Beth's return added more excitement to the deed and I was going to cum real soon. Brooke moaned lightly but I know she was holding back. With animal ferocity, I plowed into her rocking her hard.
"I'm going to cum up your ass now Brooke, get ready" I said to her quietly as I grabbed her hips real tight and went at it like mad. Within seconds I was unloading all my cum deep into her butt. I don't think I ever came as hard as I did just then. I rested there for a moment to catch my breath then rolled her over to face me. I kissed her long and hard, as I cupped her crotch with my hand feeling her hard cock.
"Thank you Brooke, you are one beautiful girl and I thank you for a great afternoon. I am glad we got to meet and hope to continue to meet in the future. There is much we still can do. If there were time I would take care of you as well, maybe later on if the chance comes up. If not, there is always tomorrow!" With that I smiled, and she smiled back knowing we would be together again shortly. We kissed and I left to go clean up.
We did continue to meet very regularly and had many more adventures but none can compare to that first day. I am still dating Beth but having Brooke on the side has made life much more enjoyable.
Comments are welcome but if your intention is to flame me, just keep it to yourself.
Freethinker32@yahoo.com