Date: Sun, 6 Jan 2008 00:21:02 -0800 (PST)
From: Jack English <texanasianlover@yahoo.com>
Subject: Rachel and Chris - Part 2 TS/TG
Rachel and Chris
by Jack English
copyright 2007, texanasianlover@yahoo.com
Part 2
In the Apartment
We managed to gather ourselves and get out of the car. We laughed and
touched each other as we stumbled to the door. Just as Rachel opened it,
she put her finger to her lips for me to be quiet.
As we walked into the entry, which was a short hallway, Rachel loudly
called "Chris, oh Chris." And as he likely thought her to be alone, he
walked into view by the sofa which we could see plainly.
Maybe I should rephrase. She walked into view.
Rachel was right on all counts. Chris was as hot as his year older
sister but with shorter hair in a pageboy style cut. Chris was dressed in
mid-thigh length skirt, bare feet, and a white blouse. Her legs were every
bit as smooth and attractive as his sister though slightly bigger but still
petite when compared to most guys.
As Chris noticed me he seemed to be shocked that Rachel would have
brought someone in the house without telling him. And, as Chris stood
looking, not knowing what to say or do, his big sister Rachel, the girl who
had been well mannered the whole time, spoke loudly to him.
"Don't worry Chris, this is Jack. I just sucked his cock and he is
about to fuck me!" she said in a very tipsy voice which clearly indicated
that she was more intoxicated from the dinner than I thought. I guess
talking about the serious issues of her family had masked her state of
mind.
Now I was a bit shocked and looked at Chris with an equal expression
of shock. That statement did not sound like the Rachel I'd been with all
night.
Next thing, again before Chris or I could say or do anything, Rachel
reached back and unclasp her little back dress and let it fall to the
floor.
Here I was. Staring at this gorgeous twenty one year old Latina with
long dark hair a perfect bronze body standing in heals and encased in sexy
black lace-front panties and a matching mid-length bustier which was what
she w ng to push those lovely tits up so high and firm.
Chris, her brother looking much like her sister, was on the other
side of the room and appeared to be shocked by seeing her this way as
well. It certainly appeared that this was not normal behavior between
them. And, all of this theater from lovely Rachel had so distracted Chris
that he wasn't any longer thinking about his appearance.
"Wow sis," he finally said breaking the silence, "you sure look hot!"
Chris' voice was just a bit lower than what you'd expect from a girl
his size but not manly in any way. He laughed as he told his sister that
she looked hot.
It was at that moment that a wave of embarrassment passed over sexy
Rachel who stood there in black lace and high heels between her boy-girl
brother and me, her date and a man twenty years older. I stepped in to
squeeze her against me and she wrapped her arms around me and began to
giggle.
"Which way to your room?" I asked.
"This way," she said as she tugged me off and through a door which
she closed as we fell through arm in arm.
Leaving Chris in the other room without another thought at the
moment, she turned her petite, sexy body toward me and began kissing me as
she unbuttoned my shirt and pulled it off. Next she undid my slacks and let
them fall to the floor as she pulled my boxers down after them.
Kneeling in front of me, Rachel again took my now very stiff cock in her
mouth and began to suck and lick as she fondled my free handing balls. I
ran my fingers through her hair on the top of her sexy head as she sucked
me and squeezed my ass and balls with her hands.
"Oh Rachel that's good," I said as she took me to the back of her
throat clearly having learned to deep throat as a good young upper middle
class American girl.
Even better, taking a hint from my previous actions with her in the
car, she took a finger to my ass and began rubbing my semen and her saliva
all over my asshole applying pressure as s deep throated my cock.
Here I was, an old man when compared to her, and I was about to come
a second time in less than twenty minutes! What a sexy, talented lover
Rachel had turned out to be. She may have been used to young college boys
having this type of recovery and stamina but if she knew what a deal it was
for me she would have been proud.
Still wearing her sexy bustier and black panties with her heels on,
she was so gorgeous to view as I looked down and saw her silky dark hair
spread across her back. Then she did it: She pressed her finger slightly
into my asshole, applied pressure to my cock with her mouth and tongue, and
looked up at me with those big dark eyes. My sphincter clamped down on her
finger as my cock began shooting come.
Rachel kept taking my much smaller load of come in her mouth and
massaged it all from my cock using her tongue and lips and free hand. She
pulled her finger from my ass and then stood up suddenly and pranced off to
the bathroom.
"Fantastic!" I said aloud quietly as I reclined on her bed and
waited for her to return. I was hoping she would leave on the lingerie as
that is very much to my liking but who was I to complain whatever she did?
In a few moments she appeared completely nude with water droplets
covering her and her long hair wet and matted against her back. She had
taken a very quick rinse in the shower and looked incredibly sexy standing
silhouetted by the brighter light of the bathroom behind her.
"Oh Jack?" she said sexily, "I've got a surprise for you."
"Stand up Jack," she commanded.
I immediately complied and she sprinted toward me leaping up on me
just before hitting. I caught her by the legs and she grabbed me behind my
neck. Her surprise was her hot pussy now rubbing against my hardening dick
as she had her little body wrapped around my much larger frame.
"Fuck me, Jack!" she demanded.
I turned and we fell to the bed where I entered her hot pussy with
her leg d around me. We kissed almost violently as I began fucking her with
as much rhythm as I could muster being held so tightly.
When she had come out of the bathroom I had gotten my first look at
her breasts and they were as firm and perfect as I had suspected upon our
meeting at the car wash. Small C to large B cups on a very petite frame
with perfect bronze skin. I moved down and licked her hard nipples as I
fucked her and she arched her back to receive me more deeply.
Having achieved orgasm twice in the past hour was going turning to a
firm asset as there is no way I was going to come before Rachel had fucked
herself silly on my cock.
I flipped her over to my favorite position with her on top of my
reclining body, impaled on my cock, and looking right at me. Her breasts
were swollen, nipples hard, and her wet hair felt cold as it danced across
my nipples. I began to massage her breasts and lift my head up to lick and
suck them. Rachel began to increase her tempo fucking my cock and began to
moan "Yes, yes" as my tongue danced across her nipples.
She quickly reached orgasm and fell against me with her warm body
against my chest as her pussy clamed down upon my cock in spasm after
spasm. Her breath was heavy and filled my neck and ear with warmth as she
recovered from her climax.
"Rachel, you are incredible. Fantastic, Tremendous," I said as she
recovered.
That brought a lifting of the head and a smile followed by a deep,
slow, sensual kiss.
Rachel's backdoor
After cuddling and falling asleep together, I woke with Rachel slowly
and lightly nibbling my neck and ear. Glancing at the clock on her dresser,
we'd slept about an hour after our hot first fuck.
I had to admit it to myself: Rachel was about the most perfect female
specimen I'd ever had the pleasure to make love with. Not just young and
pretty, Rachel was gorgeous with perfect, tan skin, an incredible petite
body, and self confidence. She seemed to understand her sexuali
As we began to kiss again and rub our bodies, we talked between kisses
and licks. Rachel was being very complimentary to me and began telling me
things about herself. She surprised me as she told me that she had only had
intercourse with two other boys. One was when she was about sixteen and
another boyfriend for over a year when she was nineteen.
I asked her how she became so good at blow jobs then. She said that
in high school she had given several of those and that is was very common
now for girls to give oral sex but refrain from intercourse. I told her
that I liked that fact as many men like oral better than intercourse but
that most women were the opposite. She actually was surprised to hear that
older women don't all like giving head.
"I like it," she said and explained that it made her feel hot and
sexy to know that she was bringing a man to such an orgasmic height.
"We like it too," I assured her.
I then told her how much I loved the fact that her pussy was
completely smooth and hairless. She seemed pleased that it turned me on and
I expanded on the subject by telling her just how much it turned me on. I
decided to demonstrate by moving my mouth to her lovely pussy and started
licking and sucking until she was shaking with pleasure.
Rachel pulled my head in tightly against her pussy as I pressed her
clit with my tongue. I moved the rough of my tongue across her swollen
clitoris and she began to buck with orgasm. Her thighs held me tight and
her hands pressed me against her shaven, smooth pussy while she enjoyed the
waves of her climax.
It was just as Rachel was relaxing again from her orgasm that we were
reminded of Chris as we heard music coming from the other room.
"I can't believe I did that!" Rachel said remembering her entry into
the apartment.
"Chris is going to kill me," she added as she remembered the whole
scene and played it out in her mind again.
"I bet if he cares about you as much as you care €™t be upset at
all," I said.
"You were obviously having a good time and she could tell," I said
specifically using the female pronoun for Chris.
"You called Chris "she"," noticed Rachel. "Chris would love that,
really she would."
"I've been trying to remember to refer to her that way too when we
are at home but it has been hard to do since she has been a he for my whole
life. At least Chris goes both ways as a name, I don't think I could handle
changing names," she added.
"Does Chris date or have girl or boyfriends over?" I asked.
"Not that I know of," she said explaining again that he hasn't been
going out in public as a female even though he looks as great as most any
girl.
"But he does use the vibrator and play with his girl pussy," I
reminded her.
"You sound like you know something about all of this," Rachel said to
me looking as if she wanted me to tell her more.
"Well, I'm not exactly unaware of cross dressers and boy-girls," I
said. I wasn't going to tell her that I'd actually had experience with the
subject first hand but I did want her to know that I was not in the dark
about the subject.
"I've read sexy stories about them online and seen pictures and a few
videos," I added wondering what her reaction would be.
Then I ventured a comment as I began massaging her asshole with my
finger as we hugged. "I've always found the ones that look fully female to
be kind of sexy."
Rachel began to wriggle as I massaged her sphincter. Then I began to
push a well lubricated finger inside and she gasped as I entered her.
"You know that the ladyboys consider this to be their pussy. See how
much pleasure they can get on the back side?" I asked as I slowly loosened
Rachel's tight muscles.
There had been no resistance from her so I continued on with the
assumption that she was really enjoying this new experiment with anal
play. I asked her how it
lubricant and she pointed to the nightstand which was in easy reach
without me pulling out. So I leaned over and grabbed the KY and squeezed a
bit out in my hand one-handed to warm it up. As it warmed I began rubbing
into Rachel's tight ass.
"Rachel, you sexy gorgeous girl, I'm going to fuck your sexy ass in a
few minutes. What do you think about that?" I asked in her ear.
"Mmmm, it sounds exciting," she said as I continued fingering her ass
and about to insert a second finger.
"It will be tight and might hurt a little bit when we start," I
said. "You'll need to work at relaxing your muscles to accommodate the
size."
"I've a confession," she said as she turned her head toward
me. "After hearing Chris' vibrator buzzing, I've found where it is kept and
have been using it on myself for months, including in my ass. It's not as
big as your cock but I know what you're talking about so go ahead baby and
fuck me. I've wanted to know what it would feel like since thinking about
what Chris must feel."
I worked three fingers into her sexy ass and then moved up with my
knees on each side of Rachel's sexy hips. Then I began to slowly press my
cock against her hole working up to penetration. As she began to push her
ass back against my cock I took that as a sign to begin to penetrate
her. All the while I was talking very softly and very dirty to her.
"I'm working my cock into your sexy ass Rachel," I'd say. "Feel my
big cock stretching your little ass, sweetheart." And, "I'm going to fuck
you in the ass you little slut."
My talking and constant pressure seemed to work well as my cock began
to slide into Rachel's tight ass. I squeezed more KY on and slowly pushed
deeper into this petite beauty. She grabbed the sheets and clutched them in
her hands but made no sounds of discomfort. Instead she moaned as if she
was feeling the pleasure of the extreme stimulation.
"How is Rachel? How does my cock feel
In a breathy voice obviously still getting accustomed to the
intrusion, she said "Wow it feels tight and full, much better than the
vibrator. I can feel the heat of your body and the throb of your heart
beat."
We stayed still for a while as Rachel's backdoor pussy relaxed around
my cock. As she began to move slowly, so did I and within a few minutes I
was taking long and deep strokes into her very tight asshole.
"Oh yeah, fuck my ass," she began to pant lifting herself up under me
to meet each stroke.
"Fuck me, oh yes, fuck me in my ass," she continued to groan.
"Your ass is so tight and hot. If you keep talking dirty to me, I'll
shoot my load right up your ass," I warned.
"Good, fuck my ass. Fuck me and shoot your hot come in my ass," she
demanded as she increased the tempo of her hip movements.
I began fucking her ass harder and faster and felt myself getting
closer to orgasm.
"I'm going to come in your ass baby," I said as I plunged as deeply
as possible.
"Come in me, do it. Come in me now," ordered Rachel.
My orgasm hit and I shot my come deeply into her ass. This lead to
Rachel panting out an excited "I can feel it, I can feel it. Wow! It feels
hot inside!"
Secretly I knew just what she was enjoying. When the ladyboy I'd met
years before fucked me in the ass after years of having used a vibrator
too, the feeling of the real flesh was incredible. And while there had been
a condom on the ladyboy's cock, I could also feel the heat of the juice in
my body.
Slowly I withdrew from Rachel's tight ass. All the while she was
telling me how great it had felt. We both trotted off to her bathroom with
me jumping in the shower as she handled other matters. A few moments later
she joined me in the shower and we soaped and cleaned each other followed
by a wonderful session of applying lotion to every inch of our bodies.
By now it was well past 3 am and I told Rachel that it w est if I
left now so as to avoid another scene with Chris. I dressed as she helped
while wrapped in a sexy little short robe. As I dressed I thought about how
fabulous Rachel is and how much I hope to keep seeing her. She must have
been thinking the same because when I had put on my shoes, she looked up at
me while hugging me and said, "I hope this is only the beginning."
I caressed her lovely hair and told her not to worry and that "I
think we'll be seeing each other every chance we get."
We kissed and Rachel walked me to the door where we kissed again and
I left.
Part 4
Rachel helps Chris
Our prediction turned out to be true. Rachel and I saw each other
exclusively for the next several months. Our mutual attraction grew far
beyond sex and we both enjoyed the company of one another. She was not
possessive and didn't bother me about my work and demands on my time,
conversely I was happy for her to be in school, working and having a wide
range of friends with whom she spent time.
It was a rare night that she did not spend with me or me with
her. And, as she was extremely feminine and very much a girly-girl, she had
fully taken to my love of fine lingerie. I'd ordered an outfit or two per
week on-line and she would find a way to surprise me wearing it. She told
me that Chris had started to notice her growing collection of expensive
lingerie and was jealous. He told her that he wished he had a lover who
would treat him as I did her.
Anal sex had become a regular part of our love making and for some
time she had used a vibrator, that I bought for her, to stimulate my ass. I
loved it when she sucked my cock and fucked my ass at the same time. But
like she had been, I desired the feeling of the real thing.
Knowing how much she cared for Chris, and aware of my own fantasies,
I started sending a lingerie package for Chris ever other week or so
too. Chris and I had still not spoken much as she would generally withdraw
to her bedroom when I was at t ought Chris was still uncomfortable having
people see her dresses as a woman.
Well sending the lingerie to Chris seemed to make a big difference in
pulling her out of her shell of doubt. After receiving the first package,
she only asked Rachel to tell me thank you. But after the second, she felt
compelled to tell me thank you personally. When I came over instead of
running away, Chris stayed in the room and told me how much she appreciated
the gifts. She surprised Rachel and me both by stepping up and hugging me
and planting a kiss on my cheek. "This is certainly new," I thought.
That evening in bed, Rachel told me that she thought that Chris had a
crush on me big time!
"There's no doubt it," she said. "Chris has the hots for you and as
your lover I can understand why!"
As she said this she lowered her mouth over my cock and began to suck
me to full tumescence and I put my head back enjoying the feeling and
thinking that just maybe I like the idea of the cute Chris having a crush
on me.
It wasn't long before Rachel was on top of me in the 69 with her
slick pussy over my dancing tongue. She also had grabbed the vibrator and
had pushed it deep into my ass as she sucked my cock. The feeling was
incredible as she pushed it in and out while taking my cock deep into her
sexy mouth.
I fingered her ass as I licked her clit and she started talking dirty
to me which always works to bring about my climax.
"Yeah, lick my pussy while I fuck your ass. I'm fucking your ass big
boy, just like you fuck me," she exclaimed.
I found myself talking back in the same manner, trading nasty
statements as we stimulated our bodies. Then I said it without thinking: "I
bet Chris would like to have a good fuck!"
I immediately thought I'd messed it up as Rachel stopped sucking my
cock and left the vibrator buried in me without movement.
Turning her head back to look at me as she rolled on to her side, she
said: "You're right, I bet een shutting himself up and running that
vibrator since you send him the packages, I know who he wants that fuck
from!"
"Would you do it Jack? Would you have sex with Chris all dressed up
in the lingerie you bought?" she asked.
I was unsure what to say but it seemed as if she was once again
trying to help Chris and was suggesting the idea. So, I ventured a cautious
yes.
"I'd make love with Chris if you were part of it. But I'd only want
it to be with you," I said.
"I mean he, or she, is your brother, or sister. Could you
participate?" I asked seriously.
She thought about it for a few moments and then said, "I'd do just
about anything to help Chris and as long as it was just touching and making
love with you, I wouldn't have a problem. It might be a lot of fun."
"Well, if you think we could manage it I'd go for it but there is one
request. I want to feel her girly cock in my ass," I said with a wry smile.
"Oooh, that would be exciting," Rachel said as she began moving the
vibrator in and out of me again and leaned back over to suck my hard
cock. In just a few moments I was shooting my come all over her mouth.
She leaned up and rubbed it into my face and used her tongue to push
some into my mouth saying, "You should get used to it if you're going to
fuck Chris!"
I figured that at some point in the future Rachel would talk with
Chris and broach the subject to gage her interest. So imagine my surprise
when I came out of the shower in Rachel's bathroom and stepped into the
bedroom to find Rachel dressed in heels, black stockings with a matching
garter belt, black shelf bra showing off her hard nipples, and deep red
lipstick on her mouth. And her sister, clearly, dressed in the most recent
outfit I'd sent. White stockings and garter, white see through lacy
panties, and white bustier. Chris looked as sexy as just about any young
college girl you could meet. She was soft, feminine, hairless and had a fac
her sister's.
One difference I could see was what surprised me as being a very sexy
bulge under the white lace panties. Chris' girl cock was fully visible and
seeing it behind the lace really turned me on. I couldn't look at much else
as I took in this surprise sight.
The two stepped toward me and felt the sexy and familiar touch of
Rachel as she ran her hands all over my naked body. She kissed me and as
she did so I felt the heat of Chris pulling into a three-way hug.
I could feel Chris' boy clit against my thigh and knew that one of
the hands squeezing my ass was his.
As I kissed Rachel, she moved my hands toward Chris and guided me to
stroke his body instead of hers. I followed her lead and began to rub and
caress Chris. Soon, she turned our kiss toward Chris inviting his mouth to
meet mine. Chris and I began to kiss passionately and Rachel went to her
knees and began to suck on my cock.
As Chris and I kissed, I treated Chris as I would any girl. I began
to kiss her neck and down her chest until I was on my knees. I was face to
face with her boy-clit. I began to kiss it through the white lace. I made
love to it through the lace while stimulating her boy pussy with my fingers
under her white panties.
"That is so HOT!" said Rachel as she sat on the edge of the bed
watching us while slowly fingering her pussy and nipples.
I thought when looking over at her that she looked HOT sitting their
stimulating herself while watching us!
"Suck Chris' little clit," she suggested lewdly.
I pulled the panties down slightly and brought out Chris' hard
cock. I looked at it for a moment and with Rachel's encouragement took it
into my mouth. It felt good to have a feminine cock in my mouth again, the
again part Rachel knew nothing of.
After sucking Chris for some time I stood up and we kissed again
sharing the slick juice. This time our cocks rubbed together as we kissed
and it felt wonderful.
"Chris, I want to fuck yo y-pussy. Would you like that?" I asked.
"Yes, very much," Chris said softy.
Rachel and I guided Chris to the bed and placed her on her back. With
her legs over my shoulders I began sucking her clit while generously
lubricating her ass with KY jelly. I fingered her a bit but she was already
loose from all the use of the vibrator. I stood up and motioned for Rachel
to put two pillows under Chris' ass which she did. Then, I put her ankles
on my shoulders and Rachel helped to hold them in place. This gave her a
great view of my cock as it slowly entered into Chris receptive boy-pussy.
Chris has practiced often so it was easy to penetrate her and she
really looked cute as her mouth gaped open as she enjoyed my cock pushing
in and out of her asshole.
Rachel seemed to really enjoy watching this and was not helping me
remain hard by fingering my ass at the same time. I was going to come soon
and there was little I could do about that so I asked Chris: "Do you want
me come inside you?"
"Yes, please come in me," Chris said.
In just a few more strokes, I reached orgasm and shot my come deep
into Chris' ass. And just as I did, Chris' clit began to shoot white cream
all over the bustier she was wearing. Apparently all of this was enough for
Rachel too as she must have been rubbing her pussy while fingering me
because she let loose with an orgasmic scream I'd not heard from her
before. As I turned to look, she was crumpling to the floor with spasms of
pleasure.
Chris was on the bed breathing hard and fondling her clit attempting
to recover from what I assumed was her first real fucking. That left me
standing with a hard cock and no relief so I moved up onto the bed and put
my cock just by Chris' mouth. Chris immediately took me between her red
lips and began to give me a blow job to rival those of her sister.
Soon I was shooting my come in Chris' mouth and she swallowed every
drop.
"That is so sexy and hot!" Rachel repeated s
she was again hugging me with her hot sexy body and watching Chris lie in
ecstasy. Rachel seemed truly pleased that she had been able to give Chris
this experience and was all smiles.
"I haven't forgotten about you," she said as she started kissing me
again.
"Chris, I want you to do something for me," Rachel said to her
sister. "I want you to get your dick hard and fuck Jack up the ass while I
watch."
The latter sentence being somewhat of a command, Chris just shook her
head in the affirmative and stood up stroking her now hardened cock.
Rachel had me lie face down on the bed with the two pillows under my
cock. She then lubed up my ass showing every detail to Chris, lecturing
aloud about how to get an ass ready to fuck. She seemed to really be
getting off on instructing Chris on how to fuck me but I doubted the Chris
needed any instruction.
I could feel Chris' stockings rubbing up against my legs as she
straddled me moving her coquette to my opening. Chris slowly pushed into me
and after a few moments had buried her entire shaft deep within my ass.
It felt great. Hot and pulsating and I was looking forward to feeling
my first shot of hot come inside without the barrier of a condom. As Chris
began fucking me harder and faster, beautiful Rachel came around and places
her bald pussy in front of my face and pulled my head into her.
Here I was with her lingerie clad boy-girl brother fucking my ass
while my head was buried in pussy of one of the sexiest girls I'd ever
met. "What at day," I thought as Chris continued to stroke in and out of my
ass.
"Chris," Rachel began to shout, "come in his ass. Shoot your come
deep in my boyfriend's ass!"
Chris was pounding be hard by now and responded to the Rachel's
shouts of "fuck him in the ass, come in him."
And just as I was about to join the chorus, Chris froze for an
instant, then he pushed deep into me and began shooting his hot come inside
me. "Wow!" lode inside. "It's just like you said," I said to Rachel who
seemed very pleased at having presided over the whole event.
After a little time had passed, Chris withdrew to his bathroom to
clean up and I did the same. When I came back into the room, Rachel was on
the bed with her legs spread and her vibrator working her pussy. Her eyes
were closed so I crept up beside her and placed my cock gently on her
lips. She took me inside and sucked me as she brought herself to orgasm
with the vibrator.
"Jack, that was the hottest thing I've ever seen in my life!" she
stated enthusiastically.
"Seeing you suck on Chris and then fuck him was incredible but seeing
him, well her, on top of you fucking your ass was just too much!!" she
said.
"I'm glad you liked it, I rather enjoyed it too." I said.
About that time we saw Chris in the door. This time dressed in a sexy
pleated skirt. She had the whole school girl look going.
"Chris, you look really hot," I said sincerely which brought a smile
to her pretty face.
"Come over here," I commanded and Chris came to the edge of the bed
standing over us.
I reached over and felt under the skirt Chris was wearing and felt
her cock under soft satin panties. I surprised Rachel and Chris by leaning
over and taking Chris' cock in my mouth again. This time I sucked Chris
until she came in my mouth. I then went straight for Rachel and kissed her
with her brother's come in my mouth and shared it with her before she could
object.
Chris just smiled as she saw what I was doing and reached over and
stroked her sister's hair while we kissed.
"Rachel," I said as our mouths parted, "do you think that Chris needs
to hide when I come over from now on? Or should she just come on in when
the door is open and join her sister in getting some good cock?"
Rachel looked up at Chris and said "I think she should come in and be
the girl she's always wanted to be."
The End.