Sarah s New Roommate
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The New Roommate
We had been friends for over twenty years; still I was nervous about
sharing my home with Ken. He was the best man at my wedding; I was the
best man at his. I am a widower; he is divorced many years now. Although
we were both in good shape financially, it did make sense to share a
single place. We only lived minutes apart and spent a lot of time
hanging out together. I was nervous because Ken did not know I like to
cross dress.
I have been a cross dresser for longer than I have known Ken, my wife
knew and supported it as long as I only did it at home. Over the years,
I have become quite good at it. I could pass in public although I would
never be called beautiful or get cat call whistles. For the last ten
years I have taken natural vitamin supplements that mimic hormones in a
safe way and although the results took a long time, I have soft, just
under a B cup breasts and an ass that is round and wider than a man's
should be. At five foot nine inches and one hundred and fifty pounds, I
do have quite a cute figure.
My wife had taught me much about make up and over the years I have
learned how to present an elegant, conservative yet sexy look. I keep my
hair a "normal" length and either mousse it into a messy look or wear
one of several wigs when I want a longer look. I am of course completely
shaven, something that has become easier as I have gotten older. I was
never very hairy and whether it was the years of shaving or just the
years, I rarely had to shave more than once a month anymore.
So why did Ken have no idea? First because I never told him, second
because I have always been very cautious. We go to football games and
play golf together but none of our activities involved changing in a
locker room, swimming or anything that would involve me wearing shorts.
So, even though we both needed the companionship and could save some
money, I was none the less nervous.
After many discussions about how to split the bills, we agreed he would
rent out his house and we would try sharing mine. Ken moved his things
in and it turned out quite well. We respected each other privacy and our
friendship actually got better. My only down side was that my cross
dressing was limited to my bedroom and only when I knew I would not be
disturbed. I was never an everyday dresser but the limited area of
movement was frustrating.
One Sunday during the second football game and after several beers, Ken
asked me if I felt our living arrangement was working out well. I told
him that yes; it was nice having someone to spend time with. He then
asked if his being there was interrupting my sex life. Not sure what he
meant, I just told him I did not have much of one anyway.
I asked him the same questions and his answers were similar. He really
did not want to put up the effort to get a girlfriend and that as much
of a hassle as a relationship was, he would rather hire a hooker.
Several beers later he added it was a shame we were not gay.
That comment surprised me because even after all my years cross
dressing, I had never had gay thoughts. Sure I own a dildo and although
I use mostly for anal stimulation; something my wife and I discovered I
enjoyed, because I had only shared dressing with her it was always a
heterosexual thing in my mind.
All I could think of to say was, "excuse me?" He laughed, I guess at the
look on my face and then added, "We get along great, like the same
stuff, and if we were gay we could have no strings attached sex and be
done with worrying about that part of our life."
I asked him if he had ever had gay sex and he responded no, that getting
a hard on over a guy was not something he thought would happen. It was
my turn to laugh and so I said, "Well maybe you never found the right
man."
Ken threw a couch pillow at me and that was the end of the conversation.
We finished watching the game and went to our separate rooms. Laying
there I began to think about the talk. At six foot tall and about one
eighty, Ken was not a bad looking guy as guys go. I had never thought
about gay sex but it occurred to me that instead of masturbating, if you
closed your eyes, having someone else get you off would be better than
doing it alone. I drifted off with that thought.
The next Friday Ken was going to be out of town and I was looking
forward to the freedom. When Friday arrived I fixed a light supper and
went to my room to change. I slipped into a simple white panty and an
underwire bra that matched; donned low heels and a simple summer dress.
I did not bother with make up or my hair.
Checking myself in the mirror, I noticed the thin dress allowed a hint
of my bra and panty to show. After dinner I curled up on the couch and
spent a quiet, uneventful evening relaxing in the pleasure of the
feminine clothes.
Locking up the house I went to my room and changed into sheer black
panties and a baby doll nightie. Lying under the covers, my mind again
drifted back to the talk we had during the football game. For the first
time I considered what sex with a man might be like. I had to agree with
Ken, two guys did not strike me as arousing. Then it occurred to me that
I did have the ability to look like a woman. Did that change anything?
As I caressed my stiffening nipples through the nylon, I tried to
imagine it was a guy doing it, specifically, Ken. Cupping my breasts and
lightly squeezing them, I closed my eyes and wondered what the
difference would be between my memories of my wife's soft lips sucking
them and Ken's male mouth.
Would his larger hands feel different as they rubbed my ass through my
panty? I knew my cock had gotten hard but I ignored it. I began to
wonder what being kissed by him would be like. It had been so long since
I had been kissed. Would I like it? Would he?
I pulled the nightie up and played with my naked breasts. Sliding my
hand down my smooth bell, I imagined it was his hand. As I touched my
hard on, still covered by the panty, I moaned aloud, fully into the
fantasy now.
Realizing that if I was aroused my fantasy partner might be as well and
that I would have to please him, I shivered. My belly felt for a moment
like it does on a roller coaster, but then settled. Reaching into my bed
table I removed the six inch gel dong I keep there.
Rolling onto my side, I held it pointing up at the ceiling and looked at
it in a new light. If that was Ken's cock I was holding, what would I
think and do? I slowly started stroking the length of it with my other
hand. The feeling of the thick molded veins and the look of the mushroom
head were suddenly sexy.
I could feel myself blush as I leaned over and for the first time placed
my mouth at the cock head. Was I really hard in my skimpy outfit
thinking about sucking a cock or was I just horny because it had been so
long?
I began to imagine Ken making moaning sounds and urging me on. As the
dildo warmed in my mouth I began to wish there were heavy balls below it
to tease. Soon I was taking half of the shaft in my mouth and sucking it
tightly. So lost I was in the fantasy that I began to hope Ken would not
cum in my mouth without warning. I pulled my off as I imagined him
saying that he needed to fuck me.
Using lube I oiled the dildo down and rolled over on my back. Spreading
my legs I placed the head at my hole and rubbed it there. Teasing the
opening by rolling the head against it soon had me begging Ken to slip
it in.
I pushed it just hard enough for the head to pop in. Usually that was
all I did; just enough to stretch my hole but no further. I had never
had anymore anal sex than that, but tonight I realized I needed more.
Getting on my knees, I slipped my panty to the side and centered it
between my legs. Bumping it against my hole, I pretended Ken was teasing
me with his big cock. Whimpering, I began to lower myself down. One inch
at a time I let him enter me. After two inches I pulled back up and then
sat down on it again taking a little more.
There was gentle pain as I worked myself down onto its full length.
Slipping my hand under the nightie again I found my breasts warm and
nipples stiff. Gently squeezing them as I imagined Ken would, I began to
hump the dildo slowly.
I could almost feel his hands on my ass and tits as I pictured myself
straddling his thick thighs, taking his cock deep inside me. Pressing
all the way down, I stopped and began squeezing the dildo with my ass
muscles. Oh Ken I said aloud, "Please cum in me, cum in my ass." As I
margined him moaning and pumping into me, my ass clenched and without
touching it, my cock spewed my own cum inside the panty I wore.
Rolling onto my back again, I left the dildo in and reached into my
panty. Scooping as much cum as I could onto my fingers, I raised my hand
to my lips and tasted it. I had never done this either, but it seemed
right. I drifted to sleep wondering if Ken's tasted the same.
I awoke Saturday with the dildo still in my ass although it had slipped
about half way out. Thinking I should be embarrassed, I was pleased to
find that I was not. Slipping out of my nightie, I washed the dildo and
put it away. I took a shower, put on boy clothes and set about the day's
errands and chores.
Ken got in around dinner time and we had a very normal evening watching
the news and then a movie. After his sixth beer and my fifth, I went to
the bathroom. While there, I peed and then put on "Lush", my favorite
eye lash thickener and lengthener. No other make, just that. Nervously I
returned to the T.V.
Ken did not notice anything. I should mention that we can both drink
quite a bit of beer and are goofy, not angry when drunk. Around our
tenth beer I said to Ken, "I normally don't do this but it is warm.
Would you mind if I wore shorts?" He shrugged and said I should wear
what I want. I almost laughed but instead went to my room to change.
I took off my jeans and jockeys and pulled on a pair on white men's
Lycra bike shorts. They hugged my round butt and if you looked you would
figure out I had no underpants on. I changed from my golf shirt to a V-
neck tee shirt that was not tight but might hint at non-male curves. I
had no intention on doing anything with Ken; I just wanted to see he
could be teased by a male.
I was nervous now because even though he was close to drunk, he might
notice how smooth my shaved legs were. I brought us both a beer and sat
on the couch with my legs curled beneath me. Nothing happened for a
while until Ken got up to get us a beer and I reached for the remote.
As I was straightening up I saw Ken standing in front of me holding the
beers with a strange look on his face. I realized he had seen down my
shirt and glimpsed a male chest that didn't quite seem to be very male.
"Everything alright?" I asked him as I took my beer.
He shook his head for a moment and replied, "Oh, yeah everything is
fine, I .. never mind." He returned to his chair but for the next
fifteen minutes I caught him glancing at me oddly. I tried not to smile
as he grew confused.
The twelvth beer was mine to get and I stood, and then bent to pick up
my empty from the table, giving him a look at my ass in the tight
shorts. Turning to take his I saw that confused look on his face again.
Returning with the beer, I saw him tugging at his crotch to readjust
himself and I was thrilled.
Walking in the room I knew that my semi hard cock was clearly outlined
in the thin shorts. I handed him his beer and sat down, stretching my
legs onto the table. The beer making me a little more bold.
"You know those shorts look good on you." I heard Ken say. "You should
like, wear shorts more often at home."
"Thank you." I said crossing my legs at the ankle.
Ken spoke again, a little slower, his words slurring just a little, "I
ah, never realized your legs were so long, kind of like a runner's"
"You don't think they are too skinny?" I asked raising one up a bit.
"No they are nice. I mean you know they look good on you."
"My wife used to tease me that my legs were better than hers. She even
dared me to put on her stockings one time." I said cautiously.
There was silence and when I looked over, Ken was staring at my legs.
"Um did you? I mean wear stockings?' He said when he realized I had
caught him.
Pretending embarrassment I did not answer for a second or two. "I did."
I admitted as shyly as I could.
"Wow." He said. "Did they feel, I mean look good? What did she say?"
Laughing I said that she loved it.
"I bet, if you know want a second opinion, just let me know." He said
covering it with a laugh. I knew he was pretty close to drunk.
"You want to see my legs in stockings?" I asked, looking over in time to
catch him adjusting his crotch again.
"Well no, but I mean if you wanted to wear a pair and needed an opinion
I would offer one." He said in an effort to back track.
"I thought you said last week that men don't turn you on?" I asked.
"They don't." He stated flatly.
"But you want to see my legs in stockings?" I asked knowing he was
getting distressed at the conversation.
"Not to get turned on. Jeesh I was just saying if you wore I pair I
would comment. I am not sure what I meant now." He said.
I laughed and said, "Sure I know your type. First it will be an opinion
on stockings, and then you will want to give your opinion on me in
panties and a bra or with heels on. Then you will have one too many
beers and try to reach into my blouse to play with my tits or ask me to
touch you down there."
Ken sat staring at me as I spoke. I am not sure if I freaked him out or
he was imagining me dressed that way. Either way he was blushing.
"I told you he slurred; I don't get turned on by guys." He stated.
I stood and walked over to his chair and standing before him I said, "So
tomorrow during the game, if I come into the room in a sexy bra and
panty, stay up stockings and high heels, maybe with a short, tight,
plaid schoolgirl skirt and a sheer blouse, you won't get turned on?"
"That would be weird but of course not." He said. I would have believed
him if he was not staring directly at my swollen junk in the Lycra
shorts.
"Well, we will just see then." I smiled and went to bed.
Ken came into the kitchen the next morning to find me drinking coffee. I
am not sure how late he stayed up but most of the beer was gone. Rather
sheepishly I thought, he said "Morning."
I replied in kind and did not mention the evening before. I actually own
all of the parts to the outfit I had described the night before and
could not help but wonder if he was thinking about it or of me in it.
Finishing my coffee I checked to see if there was anything he wanted
from the store before heading out to do the grocery shopping. With list
in hand I headed out. Two hours later I was back and the groceries put
away. Ken was not home because on Sundays he does the laundry and picks
up the beer for the game.
I was reading when he got in an hour later. He came into the living room
and we went through the weekly ritual of picking our games. The one
o'clock game started and we watched in silence. Per habit, I got us our
first beer as the second half started.
Toward the end of the third quarter Ken said, "I thought you going to
wear stockings during the game." I could hear the embarrassment in his
voice.
"Oh that's right. You wanted me to dress up as a schoolgirl so you could
give your opinion of me and then not get turned on. I remember now." I
teased.
"I was drunk and confused. It was just silly talk. You know how it is
when you get drunk." He claimed.
"I do. I saw you get drunk, stare at my ass, look down my shirt and then
challenge me to put on girlie things. All the while claiming it would
not turn you on." I said.
"Something like that." He mumbled.
"Was it something like that or was that it?" I asked.
"It might have been. But it was a drunken challenge." Ken answered.
"One that I believe in my drunken stupor I accepted." I challenged him.
"But I think we need to add a bet to it."
I could see he was confused. "A bet, what kind?"
"Easy, I get prettied up for you. If you don't get hard after say the
end of the second game, you don't have to pay rent next month." I said.
"And if I do?" He asked.
"Well while drunk you were pretty sure you wouldn't so maybe you should
get drunk again, because if you do get excited then I am going to lift
my skirt and you are going to please me orally." I smiled.
"You mean?" He said incredulously.
"Yup but don't worry you can't get turned on by a guy remember?" I
smiled again.
"Whatever." He said a touch defiantly. "Go get dressed or whatever." He
laughed.
"I think I will wait for the second game. It will give you a chance to
have more beer. Might help keep you calm." I laughed.
At the end of the game I got us both a beer and then said, "Well I think
I will go change."
Ken looked like he was afraid or nervous, perhaps both. I could feel his
eyes on me as I left the room. I had everything already laid out. In the
bathroom, thanks to years of practice I quickly lined my eyes and lips.
I filled my lips in with a glossy medium red lip gel and my eyelids in
light blue. My lashes long and thick once more and I quickly moussed and
tousled my hair before I went to the bedroom.
Stripping quickly I stepped into a pair of full coverage blue lace
panties whose matching underwire bra was stretch and I knew made my
smallish B cup breasts look sexy. White lace top thigh highs were next.
I pulled my mini plaid skirt on and zipped the back. It barely covered
the tops of the stockings and when bent over would show my panties. The
completely sheer long sleeve blouse and three inch ankle strap heels
completed the look.
Looking in the mirror, I reached under the skirt and into the panty to
make sure I was as tucked as possible. The idea was not get him excited,
not show him when I got that way. Taking a deep breath I went back into
the kitchen.
You can not see into my half the house from the TV room so while
standing at the refrigerator I called out, "Ready for another beer
honey?" as sweetly as I could.
There was a pause before I heard "Yes please."
Taking a final deep breath, straightening my back I emerged from around
the refrigerator. Confident in my step, no sissy mincing here, I can
walk in heels as well as I walk in sneakers, I walked in the room.
"Holy shit!" Ken said before he could stop himself.
"Hey sailor, you order a beer?" I asked smiling as I walked toward him,
one beer extended.
Ken took the beer without a word; I calmly went to the sofa, sat down on
the edge and crossed my legs. "Anything happen while I was gone?" I
asked innocently.
"No um, nothing." He managed.
Laughing I said, "Anything happen since I came in?"
Ken stared at me and only shook his head no. I ignored him and began
watching the game. Ten minutes later, I fluttered my eyes at him and
said, "Your turn. Mind buying a lady a beer?" I held my empty out to him
as he stood. I did not mention the slight bulge I saw as he rose.
He returned and nervously handed it to me. I made sure our hands touched
softly and briefly. "Thank you handsome." I said.
Red faced he sat in his chair again and we watched the end of the first
quarter. "So how are you doing over there?" I asked.
Flustered he glanced at his lap. "What do you mean?" He asked.
"With this week's picks of course, I am five and zero for the early
games. What did you think I meant?"
"Oh that yes I am four and one." He stammered.
Finishing my beer I slowly stood while watching Ken. His eyes followed
my every move. "Anything I can do for you?" I teased.
"What?" he asked. I knew he was not drunk, too early, at least not drunk
on beer.
Smiling I asked, "Would my sexy man like a beer?"
As he starred at me without answering I added, "Yes you horny dog, my
bra and panties do match."
"They do?" he stammered.
"Of course, but you are not attracted to men so it does not matter. Or
would you like to see?" I teased.
"UM, no, uh, a beer would be great." He answered.
We both drank that beer slower and soon the second quarter ended. When
he returned with our next one I asked, "Do you have a half time show for
me?"
He stood dead still. "What do you mean?"
"Is there anything you would like to say or show me?" I asked.
"Say?" he repeated.
"You could tell me if you think I look pretty. Or if you are a bit
turned on, course you could just show me that." I stated.
"Um, you look nice and I am sure I am not turned on." He lied.
"Oh well thank you and that's a shame. I would much rather you blow me
than not have to pay rent next month. Fortunately I have the entire
second half to change your condition." I smiled.
With three minutes or so before the start of the second half, I stood.
Facing Ken, I undid the top button of the sheer white blouse so that my
bit of cleavage was in sight and almost my bra. I slowly lifted my skirt
until it was just above the tops of my stockings.
"You promised to give me your opinion of my legs in stockings. Do you
like them?" I asked.
While I was turning slowly, skirt raised I heard him quietly gasp. "Um,
yes, your wife was right they are quite, quite shapely."
"Would you like a lap dance?" I inquired sweetly.
His hands immediately went to cover his lap. "Um, no, no thanks."
I got us a beer during the second quarter and soon it was his turn. I
was only half done when he got up but thought it was a good sign that he
had already finished his. I told him I would take another as I nursed
the one I had.
Ken returned and handed me the beer. Taking it with one hand, I took his
hand with my other. "Why don't you sit here by me Ken? That chair is so
far away."
Hesitantly he sat down. Placing his hand just above my knee on the
inside of my thigh, I released it. He left it there.
I looked at him and said, "I am nervous too. I have never been with a
man before."
I leaned back against the couch and waited. Soon his hand gave my thigh
a brief squeeze. Turning to face him I smiled. "You know you are my best
friend and I would never hurt you."
Taking my hand and placing it in his lap he said, "I know, but I am
scared. I have already lost the bet and I have never even touched a
man's, a man's penis."
My hand resting lightly on his pants easily felt the hard thickness
inside. I leaned over and kissed him lightly. I think he was surprised
but then he tentatively began to return the kiss. I felt him lick his
lips and then press harder on mine. A moment later his tongue gently
asked permission to enter my mouth.
I felt him taste the smoothness of my lip gel as I opened my lips to
accept his probe. We tongue touched for a bit and I felt him relax. He
pulled back and began to lick and nuzzle my neck just below my ear. I
sighed.
I took his hand and placed it on my right breast. He gently squeezed it,
and then kneaded it more firmly. "You r breast feels real?" He said
quietly.
"Long story, take my blouse off Ken." I urged.
Wasting no time he began to unbutton my blouse. As each button opened,
more of my bra and me showed. When he reached my waist I pulled back and
slid the top off. My nipples were stiff and poking through the thin blue
lace of the cups.
Leaning back into him I placed his hand on my breast. Immediately his
thumb began to rub the nipple. "My god, they are beautiful." He
whispered.
As his mouth dropped down and the nipple was sucked in, I gasped. His
tongue ran rough shod over the lace, sucking and gently biting my tender
tip. I grasped the fullness of his cock in his pants. I wanted to slide
that zipper down so bad.
Needing relief, I gently pulled his head away and stood. I turned away
from him and slowly lowered the zipper on my skirt. Wiggling a bit, I
dropped it from my waist, over my hips and let it fall to my ankles. My
round ass, covered in lace panties was exposed to him. Slowly I turned
around, my erect cock still pointing down but now obvious in my panties.
Sitting back down I hugged him and asked hi to strip so I could see him
naked. Sitting there in my bra and panty, heels and stockings I watched
as he slipped off his shirt and then kicked off his shoes. As his pants
slipped to the floor I was surprised he wore no underwear and pleased by
the large thick cock that emerged.
While he was still standing, I reached into my panty and pulled my cock
out of the leg opening. "Time to pay up Ken. I need you to suck me."
He knelt and took my cock in his hand. Pumping it slowly he gazed up and
smiled. "First time, I hope I do ok."
"Me too but I need you to drain me. Make all the tension of my built up
cum go away so that I am spent and relaxed when you fuck me with that
beautiful dick of yours."
He smiled and lowered his head. I have never been blown by a guy before
but he did a fine job. He took the head in, sucked it like it was his,
stroked the shaft and fondled my balls still nestled in my panty. I was
moaning and pulling my nipples as he gagged trying hard to please me. He
slowed down and began a rhythmic pumping with his mouth, bringing me
closer and closer.
I felt my balls tighten. I looked down and saw him staring at me, I told
him I was going to cum. He sucked harder. Taking his mouth off he said,
"Cum in my mouth." He barely got his lips back on my cock as it exploded
between his soft lips.
As I was breathing deeply and trying to get my senses back, utterly
drained, I felt him pull my panties off and pull me to the edge of the
couch. Eyes closed, satisfied, I felt his cock head touch my asshole. My
legs opened wider on their own.
I heard myself whisper, "Fuck me Ken. Take me please."
I was so relaxed, so drained that there was no pain. My ass opened for
him like he had been fucking me for years. The thick veined meat of his
cock slipped inside like I was Jell-O and he began to slowly pump its
length into me. I began to pump back, eyes still closed, lost in the
pleasure of the cock fucking me gently.
His hands undid my bra and my breasts fell free, I felt him lean in and
kiss my nipples, I wrapped my stockinged legs around his ass and pulled
him deep. I felt his cock start to throb, felt my own once again
thickening and begged him to fuck me.
"I love you." He stated as wave after wave of cum pulsed into my ass.
The cock spearing me swelled and thickened, causing my rear entry to
clamp on it. My half hard cock dribbled out a second orgasm as his
mushroom brushed my prostrate.
I remember little else from that evening.
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