thedeep
04-16-2005, 11:12 AM
MY STEPSISTER WAS A SHE-MALE
By Stephen
I won't bore you with all the crap so Ill make try and get you up to
speed quick. My parents divorced when I was a kid and I lived with my
mom most of the time (I was an only child). I moved away when I went to
college. By the time I started grad school I had my own place and
things were going fairly good.
About that time my dad married this lady who had a daughter that was
about my age. I met her at the wedding and I thought she was a real
dish. Her name was Sheila, and she was everything I looked for in a
woman--she was tall, stacked, a great body, light brownish hair and
I thought she looked kinda like Meg Ryan with a bigger curves. We
talked some and hit it off I suppose but the wedding was always in a
panic and we didn't get any farther than that.
So about a year goes by and my dad called and said Sheila was
transferring to my college and could she stay with me while she got
things squared away? I said sure. I liked living alone but I had no
girlfriend and I was too busy to make many friends and I was kind of
lonely, and I figured it might be nice to having someone around.
I picked her up at the airport and managed to get everything into the
truck. She packed like she was going around the world. She had a
steamer trunk--no shit--a real steamer trunk, the kind rich people
loaded with clothes and accessories when they were going to Europe on
the Queen Mary. And she still had other bags and boxes besides. I
thought about dropping her off at the Holiday Inn but was wearing a
t-shirt that stretched across her suculent tits and I just couldn't
think straight. She was gorgeous, just like I remembered, and we got
along immediately.
The big problem was that I had a one-bedroom apartment. I was all for
being a good host but I thought it was ridiculous to give up my bed
indefinitely. I'd shoehorned a queen-size bed into that bedroom and I
didn't want to give it up for good. We quickly worked out a plan where
wed alternate on a weekly basis. I had one week on the bed and the next
week on the sofa, and we'd alternate like that.
I got her moved in and we went about our lives. We were both busy with
school and work so we didn't go out much, and we ended up becomming quick
best-friends.
Now I'd never lived with a woman before and it had been a while since I'd
gotten laid, so I found myself getting distracted by Sheila a lot. I'm
normally not a nosy person but we both did each other's laundry, and one
day I was bringing back a load of laundry while she was gone and I just
found myself going through her underwear. Her panties were 36 inch
waist and largish (they weren't bikini style). Her bras were 36-Cs and
lacy and I thought they were great. I spent a lot of time imagining her
wearing one, and I was hoping the time would come when she'd walk around
the house in one. But it hadn't happened. I hadn't gotten any glimpses
of her naked. She was always wearing clothes or a robe or something.
All this was weighing heavily on my mind and I went into a period when
it seemed like I was horny and hard all the time. I started jacking off
in the shower or when I knew she wasn't home. But one time it was my
night on the sofa, it was late and I couldn't go to sleep and my dick
was a broomstick. And after tossing and turning I decided fuck it I'm
beating off. I started real easy a first, but I as I got relaxed I
really got into it.
And then all of a sudden I look up and there she is, standing in the
middle of the room looking at me, and I think OH SHIT. She just smiles
and says she wanted a drink and to go ahead because she doesn't care.
I waited until she went back to her room, and I really blew a load.
I wouldn't have thought much of it but it began happening a helluva lot
of the time. For awhile it seemed like I couldn't touch my dick without
her walking in. It got so bad it became a joke with us, and with that a
lot of the pressure was off. She didn't care that I did it, and she even
seemed to like it.
This went on for about a month, and then it was time for spring break.
We both finished up our midterms and on Friday night we went out to and
got smashed. We were at a party and it was fun watching all the guys
drooling all over Sheila, and they knew I got to go home with her.
It was right at the time where we normally swap our sleeping
arrangements, and it was her turn on the couch. But while she was
showering I passed out on the sofa.
Does anyone not know what happens next?
I woke up in the middle of the night, took a whiz, and I remembered it
was my night in the bed so I climbed in. I didnt notice her at all. I
just hit the mattress and I was out. The next thing I knew it was
bright and the sun was coming in through the windows. I was lying on
my back, tent-poleing the covers, so I got up and took another whiz,
and came back into the bedroom.
I looked down at Sheila, who was asleep on her back. The covers were
down around her belly-button, and she was topless. She had a beautiful
set of tits. They were well-rounded and firm without being rockhard.
The nipples were like pencil erasers and the aereolas were about the
size of silver dollars, and a luscious dark pink. Her hair cascaded
around her shoulders and a few licks touched her nipples.
Out the bottom of the sheet were two long, lovely legs.
I looked at her and my dick was as stiff I'd ever felt it. I thought the
knob would pop off from the pressure. But I kept thinking, "What's wrong
with this picture?"
Then it hit me. She was tent-poleing the sheet.
She was really out of it, I could tell. Not light, dreamy sleep, but
dead to the world sleep. I was horny and out of my mind with lust, and
I'd never seen an erect dick before (other than movies, and not counting
my own), so I just had to look.
I was real careful and I pulled the covers back and noticed her squirm a
little, and then she was nude. I thought I was dreaming. Her dick
looked about like mine, but it was on her body! She had a smallish
set of nuts, though, and she'd shaved most of the hair around it. It
looked like a female version of a dick--pink and feminine and smooth,
not red and hot and kinda ugly like mine.
I couldn't help myself, I touched it. I put my fingertips on the base of
it and rubbed it a little, and watched Sheila squirm. I rubbed it some
more and I was really getting off on watching her writhe in her sleep.
She had a little smile on her face.
I went to the bathroom and got the lube. I sat down on the mattress so I
could get a better position and I wrapped my lubed hand around it and
did it right. At this point Sheila woke up.
For a minute I thought she was going to have a heart attack, and then
she realized what was going on and just relaxed while I kept stroking.
I said good morning and talked to her real smooth and quiet, asking her
how she felt, and she just smiled and arched her back and answered in the
same tone of voice. She started playing with her tits while I stroked
her, kneeding and caressing and teasing, while her breath got faster.
Then she went rigid and shot cum all over her belly and my hand. I took
it easy, knowing how sensitive I get when I cum, but I kept milking her
dick until it was dry.
After that we got all the talking done. How and when I'd found out.
I wasn't grossed out and I wouldn't throw her out. In fact I found it
a big turnon. She said it felt like a huge weight was off her
shoulders, that she didn't have to hide it from me now.
We both had some stuff we had to do, and though I wanted to ignore it
all, she said she'd make it up to me later, so we about our errands.
That night, after dinner and everything, we went to bed early. I'd
climbed into the sack. Christ I was nervous. It was one thing to do
this sort of stuff while still half-drunk in the morning, but now I was
thinking clearly and feeling real weird about it all. But the minute
she walked in all that went out of my head. She wore a semitransparent
robe and had her fixed great. She pulled the robe tight across her tits
and then undid it and opened it up, and I was rock hard again. She was
wearing a lacey red bra and matching panties, and the only thing that
looked different was the bulge in her crotch. That really made me nuts.
She teased me, playing with her tits and tracing the outside of her cock
in her panties to make it stiff. The panties looked like they were
going to pop. She undid the bra and climbed onto the bed and straddled
me and stuck a big tit in my mouth, and she rubbed her dick across my leg.
I moved my mouth over her tits like they were icecream. They were better
than any I'd ever had. By the time I was done she was hot and panting.
She was on her back and looking at me, pleading, and I thought fuck it,
I'm doing it. I went down to her crotch gave her cock a real quick lick
and realize my tongue wasn't going to shrivel up, so I did it again. Her
cock was hard and hot, just like mine, but smooth like her skin. I
worked it over just like I'd have done my own if I could, and with her
hands in my hair, I finally got the nerve to inhale it.
It was neat. Like a big sausage but I knew it was alive and loving it.
I licked it and ran my teeth over it, ran it all around my mouth and
pumped up and down on it. It took me a few minutes to get used to it
but I quickly decided it was cool, and Sheila was just going nuts. She
was bouncing and panting and carrying on, and that just made it all
better. When I knew she was going to cum I pushed it back as far as I
could without gagging and let it go in my throat. I had to fight the urge
to puke, but with a few swallows I got it, and then I cleaned up the rest.
I'll admit I don't like the taste of cum. It's like laundry bleach to me,
but once I got past the idea that semen would poison me I wasn't bothered
much by it. And if my old girlfriends could do it, I could.
Now Sheila had shot twice today and I hadn't come at all, so we both knew
it was time. I wasn't sure what to do, but she had an idea. She was
real limber, so she pulled her knees up against her chest, lubed up my
pole and led me in her backdoor. We were doing the missionary! Normally
the missionary doesn't do much for me, but I could kiss her (and how), I
could suck on her tits, and the feeling of her cock and balls rubbing my
belly while I pumped her was out of this world. I shot off way too soon
even though I kept trying to hold off.
She gave me a jack-off show, how cool it was to have her cock in one
hand and a beautiful breast in the other, until I was hard again. She
washed me off and gave me the head of my life.
For her turn, she lubed me up and took me doggie-style. I really didn't
want to do it at first--I thought that was too much, but she was laying
across me holding me tight--her tits rubbing my back and her hair in my
face and her lips on my ears, her hands on my nipples and my chest and
her dick sliding easily in and out of me. The prostate stimulation made
me writhe in ecstacy. She came inside me and jacked me off to another
incredible blast at the same time.
We collapsed on the bed and fell asleep.
It was the beginning of a beautiful relationship.
The End
:jo
By Stephen
I won't bore you with all the crap so Ill make try and get you up to
speed quick. My parents divorced when I was a kid and I lived with my
mom most of the time (I was an only child). I moved away when I went to
college. By the time I started grad school I had my own place and
things were going fairly good.
About that time my dad married this lady who had a daughter that was
about my age. I met her at the wedding and I thought she was a real
dish. Her name was Sheila, and she was everything I looked for in a
woman--she was tall, stacked, a great body, light brownish hair and
I thought she looked kinda like Meg Ryan with a bigger curves. We
talked some and hit it off I suppose but the wedding was always in a
panic and we didn't get any farther than that.
So about a year goes by and my dad called and said Sheila was
transferring to my college and could she stay with me while she got
things squared away? I said sure. I liked living alone but I had no
girlfriend and I was too busy to make many friends and I was kind of
lonely, and I figured it might be nice to having someone around.
I picked her up at the airport and managed to get everything into the
truck. She packed like she was going around the world. She had a
steamer trunk--no shit--a real steamer trunk, the kind rich people
loaded with clothes and accessories when they were going to Europe on
the Queen Mary. And she still had other bags and boxes besides. I
thought about dropping her off at the Holiday Inn but was wearing a
t-shirt that stretched across her suculent tits and I just couldn't
think straight. She was gorgeous, just like I remembered, and we got
along immediately.
The big problem was that I had a one-bedroom apartment. I was all for
being a good host but I thought it was ridiculous to give up my bed
indefinitely. I'd shoehorned a queen-size bed into that bedroom and I
didn't want to give it up for good. We quickly worked out a plan where
wed alternate on a weekly basis. I had one week on the bed and the next
week on the sofa, and we'd alternate like that.
I got her moved in and we went about our lives. We were both busy with
school and work so we didn't go out much, and we ended up becomming quick
best-friends.
Now I'd never lived with a woman before and it had been a while since I'd
gotten laid, so I found myself getting distracted by Sheila a lot. I'm
normally not a nosy person but we both did each other's laundry, and one
day I was bringing back a load of laundry while she was gone and I just
found myself going through her underwear. Her panties were 36 inch
waist and largish (they weren't bikini style). Her bras were 36-Cs and
lacy and I thought they were great. I spent a lot of time imagining her
wearing one, and I was hoping the time would come when she'd walk around
the house in one. But it hadn't happened. I hadn't gotten any glimpses
of her naked. She was always wearing clothes or a robe or something.
All this was weighing heavily on my mind and I went into a period when
it seemed like I was horny and hard all the time. I started jacking off
in the shower or when I knew she wasn't home. But one time it was my
night on the sofa, it was late and I couldn't go to sleep and my dick
was a broomstick. And after tossing and turning I decided fuck it I'm
beating off. I started real easy a first, but I as I got relaxed I
really got into it.
And then all of a sudden I look up and there she is, standing in the
middle of the room looking at me, and I think OH SHIT. She just smiles
and says she wanted a drink and to go ahead because she doesn't care.
I waited until she went back to her room, and I really blew a load.
I wouldn't have thought much of it but it began happening a helluva lot
of the time. For awhile it seemed like I couldn't touch my dick without
her walking in. It got so bad it became a joke with us, and with that a
lot of the pressure was off. She didn't care that I did it, and she even
seemed to like it.
This went on for about a month, and then it was time for spring break.
We both finished up our midterms and on Friday night we went out to and
got smashed. We were at a party and it was fun watching all the guys
drooling all over Sheila, and they knew I got to go home with her.
It was right at the time where we normally swap our sleeping
arrangements, and it was her turn on the couch. But while she was
showering I passed out on the sofa.
Does anyone not know what happens next?
I woke up in the middle of the night, took a whiz, and I remembered it
was my night in the bed so I climbed in. I didnt notice her at all. I
just hit the mattress and I was out. The next thing I knew it was
bright and the sun was coming in through the windows. I was lying on
my back, tent-poleing the covers, so I got up and took another whiz,
and came back into the bedroom.
I looked down at Sheila, who was asleep on her back. The covers were
down around her belly-button, and she was topless. She had a beautiful
set of tits. They were well-rounded and firm without being rockhard.
The nipples were like pencil erasers and the aereolas were about the
size of silver dollars, and a luscious dark pink. Her hair cascaded
around her shoulders and a few licks touched her nipples.
Out the bottom of the sheet were two long, lovely legs.
I looked at her and my dick was as stiff I'd ever felt it. I thought the
knob would pop off from the pressure. But I kept thinking, "What's wrong
with this picture?"
Then it hit me. She was tent-poleing the sheet.
She was really out of it, I could tell. Not light, dreamy sleep, but
dead to the world sleep. I was horny and out of my mind with lust, and
I'd never seen an erect dick before (other than movies, and not counting
my own), so I just had to look.
I was real careful and I pulled the covers back and noticed her squirm a
little, and then she was nude. I thought I was dreaming. Her dick
looked about like mine, but it was on her body! She had a smallish
set of nuts, though, and she'd shaved most of the hair around it. It
looked like a female version of a dick--pink and feminine and smooth,
not red and hot and kinda ugly like mine.
I couldn't help myself, I touched it. I put my fingertips on the base of
it and rubbed it a little, and watched Sheila squirm. I rubbed it some
more and I was really getting off on watching her writhe in her sleep.
She had a little smile on her face.
I went to the bathroom and got the lube. I sat down on the mattress so I
could get a better position and I wrapped my lubed hand around it and
did it right. At this point Sheila woke up.
For a minute I thought she was going to have a heart attack, and then
she realized what was going on and just relaxed while I kept stroking.
I said good morning and talked to her real smooth and quiet, asking her
how she felt, and she just smiled and arched her back and answered in the
same tone of voice. She started playing with her tits while I stroked
her, kneeding and caressing and teasing, while her breath got faster.
Then she went rigid and shot cum all over her belly and my hand. I took
it easy, knowing how sensitive I get when I cum, but I kept milking her
dick until it was dry.
After that we got all the talking done. How and when I'd found out.
I wasn't grossed out and I wouldn't throw her out. In fact I found it
a big turnon. She said it felt like a huge weight was off her
shoulders, that she didn't have to hide it from me now.
We both had some stuff we had to do, and though I wanted to ignore it
all, she said she'd make it up to me later, so we about our errands.
That night, after dinner and everything, we went to bed early. I'd
climbed into the sack. Christ I was nervous. It was one thing to do
this sort of stuff while still half-drunk in the morning, but now I was
thinking clearly and feeling real weird about it all. But the minute
she walked in all that went out of my head. She wore a semitransparent
robe and had her fixed great. She pulled the robe tight across her tits
and then undid it and opened it up, and I was rock hard again. She was
wearing a lacey red bra and matching panties, and the only thing that
looked different was the bulge in her crotch. That really made me nuts.
She teased me, playing with her tits and tracing the outside of her cock
in her panties to make it stiff. The panties looked like they were
going to pop. She undid the bra and climbed onto the bed and straddled
me and stuck a big tit in my mouth, and she rubbed her dick across my leg.
I moved my mouth over her tits like they were icecream. They were better
than any I'd ever had. By the time I was done she was hot and panting.
She was on her back and looking at me, pleading, and I thought fuck it,
I'm doing it. I went down to her crotch gave her cock a real quick lick
and realize my tongue wasn't going to shrivel up, so I did it again. Her
cock was hard and hot, just like mine, but smooth like her skin. I
worked it over just like I'd have done my own if I could, and with her
hands in my hair, I finally got the nerve to inhale it.
It was neat. Like a big sausage but I knew it was alive and loving it.
I licked it and ran my teeth over it, ran it all around my mouth and
pumped up and down on it. It took me a few minutes to get used to it
but I quickly decided it was cool, and Sheila was just going nuts. She
was bouncing and panting and carrying on, and that just made it all
better. When I knew she was going to cum I pushed it back as far as I
could without gagging and let it go in my throat. I had to fight the urge
to puke, but with a few swallows I got it, and then I cleaned up the rest.
I'll admit I don't like the taste of cum. It's like laundry bleach to me,
but once I got past the idea that semen would poison me I wasn't bothered
much by it. And if my old girlfriends could do it, I could.
Now Sheila had shot twice today and I hadn't come at all, so we both knew
it was time. I wasn't sure what to do, but she had an idea. She was
real limber, so she pulled her knees up against her chest, lubed up my
pole and led me in her backdoor. We were doing the missionary! Normally
the missionary doesn't do much for me, but I could kiss her (and how), I
could suck on her tits, and the feeling of her cock and balls rubbing my
belly while I pumped her was out of this world. I shot off way too soon
even though I kept trying to hold off.
She gave me a jack-off show, how cool it was to have her cock in one
hand and a beautiful breast in the other, until I was hard again. She
washed me off and gave me the head of my life.
For her turn, she lubed me up and took me doggie-style. I really didn't
want to do it at first--I thought that was too much, but she was laying
across me holding me tight--her tits rubbing my back and her hair in my
face and her lips on my ears, her hands on my nipples and my chest and
her dick sliding easily in and out of me. The prostate stimulation made
me writhe in ecstacy. She came inside me and jacked me off to another
incredible blast at the same time.
We collapsed on the bed and fell asleep.
It was the beginning of a beautiful relationship.
The End
:jo