My Sister's Boyfriend

I remember when I was staying at my aunt's house.  She new of my cding so I new I was always safe to dress there.  Well as I was staying there.  My aunts house was located in the same city as where my  sis was going to college at.  Which was also kewl as she was the one that helped me with my pantyhose fetish.  Well since my aunt was going to be out of the house I decided to do a little dressing up.  So I went into my room that I was staying in and pulled out some of the fem things that I brought in my suitcase.  I pulled out some coffee colored pantyhose and slid them on and put my bra on.  I had some tight fitted jeans my mom bought me that still fit.  I put those on and then put on a red and white stipped top.  Pulled out some black strappy 3 1/2 in platforms.  I pulled out my wig and make up and finished up the dressing right there.  I decided to put on my aunts jean jacket as she had one that had harley davidson on the back.  After that I was walking around the house and just doing little things washing the dishes and some laundry.  I thought I would love to be dressed like this and be doing house work.  As I got done putting a load of laundry in.  I came up from the basement and there was my sister;s boyfriend in the living room.  He didn't see me but he heard the basement door as I was trying to close it and hide.  As the door had a squeeky sound to it.  I thought **** ******* door.  He said hello.  I didn't say anything he said hello again.  I thought well you wanted to dress up and now that you think of it you didn't lock the front door.  I also thought could be worse could have been a rober.  So I opened the door and came out of the basement so to speak literally to my sister's boyfriend anyway.  He just looked at me and didn't know what to say.  Then he smiled and kind of had a laughish sound to like why are you dressed like that and that he is waiting her for my sis.  All I could say well she isn't here yet.  I  said is she supposed to meet you here.  He said yeah. I said you can wait here if you want.  I walked past him.  He said you know you never answered my question.  I said whats that.  He said why are u dessed like that.  I was nervous but when your back is to someone you seem braver as you don't seem them.  I told him because I like to.  He said does anyone else know of you dressing like that.  I said yeah there are a few.  He said like who I said a few.  As I was trying to avoid anymore questions and feeling anymore embaressed.  Trying to make it to my room.  He followed me to the door.  He said so you like to dress like that.  I told him yeah.  He said are you attracted to men when you are dressed like that or do you just like women.  I was feeling flush but excited because I kind of had feeling where this was going..   I told him that I was attracted to men while I was dressed.  He said are you attracted to me.  I said yeah a bit you are kind of cute.  He said really.  As he walked in he closed the door.  I was nervous as I thought if this happens what if my sis or aunt come home and catch us.  He stepped forward and started to hold me then he leaned forward and kissed me on the lips.  I couldn't believe I was starting to make out with my sis's boyfriend.  I sat down on the bed and he undid his pants and pulled his **** out.  He said would you suck it for me baby.  I said yes and begin to give him head.  He was breathing heavy and saying oh yeah baby suck it. I was getting really horny by now and wasn't even thinking of my sis or aunt by this point.   As I started to taste his pre ***.  He stopped me and asked if he could do me doggy style.  I said yeah you can.  I took my shoes and jeans off and was still wearing my pantyhose, bra, ******** top, and my aunt's harley davidson jean jacket.  He said go ahead and put your heels back on.  So I put my heels back on and he pulled my pantyhose down just enough.  So he could slide it in.  He had a rubber which he must have intended to use on my sis but here he was using it on me.  It hurt a bit when he slid it in as he was about 6 to 7 inches.  But if felt so good.  I started to loosen up and relaxe after a bit.  By then he was going a little faster and harder.  We were so into it that we didn't even here the door open up.  And you guessed it.  MY SIS.  She said WHAT THE **** IS GOING ON AND WHAT THE **** ARE YOU DOING!  He stopped and pulled out.  Now that hurt a bit.  I pulled up my pantyhose and sat far back on the bed. Grabed my jeans and tried to cover myself as they started to argue.  I got up and closed the door.  I was think of my god oh **** what am I going to do.  All I heard was the front door shut.  Then I heard a knock at the door.  My sis came in.  I was still sitting there.  I got up and took my heels off.  As I was starting to take everything else off.  My sis said so how was he.  I was like um uh um oh you mean your boyfriend ok I guess.  She looked at me you guess you sure looked like he was more that ok.  I was so nervous and scared I thought I was going to throw up.  As I looked up at her to tell her I was so sorry she was smiling.  I said why are you smiling.  She said my boyfriend went out on me with my brother.  You can't tell me that isn't funny.  I said it is a little but I am truly sorry about that.  One thing led to another and then there we were.  She told me that she wasn't mad as she was looking for a reason to break up with him as he was a controling sometime psychopath ****.  So I became the reason in a weird sort of way.  As I was feeling kind of relieved for helping her out but kind of weird for her catching me.  I started to finish getting undressed.  She asked are those the pantyhose I bought you  last week.  I said yeah.  She said well at least he didn't rip them or cream on them as they were kind of expensive.  I said I know huh.  I told her that would have made me mad.  She smiled and said yeah right you were to into it you wouldn't have cared.  I smiled and said yeah.  She said well I would have bought you another pair anyway as what are big sis's for.  I smiled and when I was done finishing getting undressed and dressed back into my male clothes.  She followed me into our aunt's room and said you borrowed her jacket I said yeah.  She said you know from a sis to a brother you did look pretty hot in your **** attire.  I bloushed big time.  She smiled and we both laughed at the comment and how it was said.  Then she went into the living room and I went to the bathroom to wipe off my make up.  And to ponder and take in on just what all happened.  What a crazy afternoon.

silkiehosewearer silkiehosewearer
31-35, M
21 Responses Sep 20, 2009


Dude that must have been akward but at least it wasn't ur aunt that caught u

<p>You have a very broad minded sister and a woderful relationship with her. Treasure all of that as the two of you grow older. Love the story. Thanks.</p>

Great sister ;-)

lolz oh what a story, thanks for sharing.

Thanx sweety xoxox

Fabulous sweetie<br />
Hugs<br />

That was a hot story.Just think about if your sister was the controlling one and had her boyfriend get dressed up and you two were forced to play .<br />
<br />
Jasmine (Bay area ca,)

What a wonderful story. Your sister is very sweet. I'm still waiting for my first **** in my *** but hope I get to experience it soon.

i was shooting some pool one night in a small bar with a separate pool room,when this tall man walked in and went into the bar and came back and was watching me shoot pool.i was wearing some "poured into"jeans,and a cute sweater,full set of matching panties and bra and a pink i missed a few shots,he came over to he leaned over me,i spread my legs apart a little,and he leaned against me to help me make the next shot,and i could feel his manhood pressing into my butt cheeks,and without a thought i gave a little wiggle!,then he asked me what i was having,and i said tnt's,he said he'd be right back,and as we finished our drinks,he said he worked foe the railroad and was staying in a motel and asked if i'd like to go back with him!and i said yes!.we had another drink and smoked one and then he asked me if i'd ever been****** and i said no,i'm still a virgin,but i would like to pleasure you! he said YES,so i undid his jeans and pulled out his****which was 9" long! so i took him and gave him my best,and he lasted almost 30 minutes my jaws were tired! after he caught me in the pool hall dressed in some of my girl finery ,he called me every time he was in town,and became my secret boyfriend..and then as i was close to my golden b-day,i called him and asked i could come to his house,and he said YES, car was full of gas,i had just got out of a bubble bath,put on my bra,panties,a mini skirt,and a very pretty velvet top...strapped sandals w/ a2 1/2 heel in black, a black leather jacket and i was off! 250 miles later,i found his house,and went up to the door and before i knocked it opened.and was welcomed in to a room with 5 ladies in said hi i'm susan,alexs' sister..he got called out and won't be home until late,so we're going to take you shopping..and they did and we spent about 7 hours and i bought a way cute floral dress and then we went back to the house were they redid my makeup,and curled my hair,and gave me some love tips since i was a virgin,and then they all left! and alex came home..god i was it turned out,he was gentle and considerate,and very long lasting,time after time.i stayed for three days,was no longer a virgin,and his sister and her friends introduced me to certain sanitary supplys so i would'nt mess up my panties on the drive home,and i must admit,tampons and maxi pads after losing my cherry tied my girlhood together

thrill and crazy


I did feel all gurly and slutty. And to be honest he was real good 2. knew how 2 make me feel all fem inside and out.

great experience you had! must have felt so girly and sluty to be ****** like that by your sister's bf!<br />

that sounds wonderful. what is it like, being with a man? i wouldn't know where to start

I exuded so much pre-*** reading this that I thought I'd ********** and not felt it, so I *********** with all that lovely pre-*** over me while reading again and really ********** ...wonderful, thank you for the story.

Awesome story!! Really hot and fun you lucky devil!

No she didn't know. He would come by the house when my mom was still at work. I sometimes would go with him in his truck. And we would go somewhere private like his mom's house or grandma's house.

Bummer about not being able to finish with your sis there. If I were you, I'd love to look her in the eye while her (ex)bf came in my ***.

probably me giving him head I a think. Although he did seem to like that I was in pantyhose though. The crazy thing was that after my sis and him broke up. We ended up seeing each other for a bit. Which was kind of nice and kinky in a cool kind of way.

No I was with a few but not many before him. But he did feel the best out of all of them. I have been with a few of them since. And yes I was always dressed more or less.