Date: Sun, 28 Jun 2009 01:46:39 -0400
From: indybicd@aol.com
Subject: Adventures with Creative Endeavors 3
Adventures with Creative Endeavors, Inc.
By
Stephanie (indybicd@aol.com)
Part 3: Tranny Mentoring
Stephanie had been working for Creative Endeavors, Inc. for about a
month now and had been on several dates. All of her dates so far had been
with so-called "tranny-chasers" or "male admirers", which wasn't really
unexpected for her nor particularly unpleasant but she always thought it
was interesting the lengths that some people would go in order to be able
to pretend to themselves that they weren't gay or had any gay inclinations
when they were purposely seeking out with chicks with dicks. Creative
Endeavors, Inc. was specifically marketed as providing tranny escorts,
which some people clearly wanted- if their current level of business was
any indication. Her recent dates (and dare she forget to mention the sex)
had been pleasant enough but nothing could really compare to her first date
with Richard. That "date" had turned into so much more than that for her.
However, having sex on a regular basis with a variety of people, as well as
enjoying an improved standard of living because of the extra cash coming in
from her "side job" made the shortcomings in her work seem largely
unimportant.
Today, Susan had a new client for her who stated that he sought out
their services because he said that he wanted to be "feminized". It was a
different kind of request than the agency normally received but apparently
it was one which Hannah felt that an agency owned, operated, and staffed
specifically by trannies seemed to be uniquely positioned to provide.
Besides, who among them would just turn down the money for what seemed like
a simple request for them? Stephanie could remember back to her awkward
first days of crossdressing and how she didn't really have anybody else, at
least at first, to teach her about becoming more feminine and thought that
the idea of "mentoring" a budding tranny in the fine art of feminine
transformation could be a fun experience. As such, Stephanie ultimately
decided to accept the "assignment".
Per the terms of the arrangements made between Creative Endeavors,
Inc. and the client, "Matt," the agency had agreed to purchase all of the
necessary supplies and accessories for Matt's "feminization" including
clothes, a wig, makeup, etc. provided that Matt paid them upfront for the
estimated cost of everything, as well as the standard cost for the "date",
which he had eagerly provided. Susan had gone shopping earlier in the week
and purchased everything Stephanie would need for Matt. Stephanie met her
at the office that Friday afternoon to pick up everything. The
arrangements had her going directly to Matt's home instead of meeting him
at the agency- which had been the standard practice for her dates so far.
As soon as Stephanie had loaded the container with all of the supplies she
needed, she proceeded to Matt's house without delay.
After about 20 minutes on the road, Stephanie pulled her car into the
driveway of a medium sized 2-story home located in a pleasant-looking
residential neighborhood. Stephanie got out of her car and went to the
backseat where she pulled out the supply container. She then lugged the
supply container with her to the front door and rang the doorbell at the
same time trying desperately to hang on to the container. Matt had been
instructed to prepare a bath with some conditioner prior to Stephanie's
arrival, so she wasn't surprised at all for him to answer his door with
nothing else on him other than a wraparound towel.
"Hi," he said warmly, as he welcomed her into the home. "You must
be Stephanie, right?"
"Hi," said Stephanie, as she struggled to hold onto the supply
container. It wasn't particularly heavy but it was rather awkward. "Yes,
I'm Stephanie. I'd offer to shake your hand but my hands are kind of full
just trying to hold on to this container- as you can probably tell," she
added.
"Can I take that for you," he offered politely.
"Sure," replied Stephanie eagerly. She was relieved to not have to
hold onto that awkward container any longer. She breathed a sigh of relief
as Matt took it from her. "Thanks a bunch!"
"No problem," he replied pleasantly. "By the way, my name's Matt."
"It's nice to meet you, Matt. As you know, I was sent over here by
the agency to provide you with the services that you had requested."
"Come on in," he invited. "I see that you have everything that I
paid for and I have the bath all ready to go- as you can probably tell," he
stated, glancing down at his wraparound towel.
"Yes, I can see that. Why don't we go on upstairs and get started,
then? I'm sure you're eager to make the most out of your time and money."
"Absolutely," Matt agreed. "I can't wait," he stated eagerly.
Stephanie followed Matt up the stairs to a small bathroom located on
the second floor of the home. Matt laid the supply container on the floor
of the bathroom. Stephanie could see that Matt had indeed drawn up a bath
and could smell an aroma coming from the bath that she thought smelled like
Vaseline intensive moisture conditioner- something that she used at home at
lot.
"Go ahead and hop on in," she directed. "The first thing we'll be
doing is shaving most of your body hair, which the bath and conditioner
will help with."
"O.k.," he replied as he obediently removed his wraparound towel and
tossed it to the floor. Then he turned around and climbed into the tub.
Stephanie could not resist sneaking a quick peek at his beautiful cock and
ass and felt a little tingle between her legs. Stephanie almost felt
embarrassed that she was thinking of other things than her job at hand.
Matt settled himself into the tub and when he was all stretched out
he closed his eyes and looked like he was resting for a couple of minutes.
Stephanie knelt on the floor in front of the tub and stared at him. She
thought he looked like very attractive guy and she felt like she could
almost certainly make him look like an equally attractive-looking woman-
with the proper attention to detail, of course. After a couple of minutes,
he opened his eyes and looked at Stephanie and grinned. "O.k., I'm ready,"
he advised.
Stephanie took this as her cue to start her work. She got the
razor that Susan had purchased out of the container, as well as some
moisturizer and began methodically and carefully shaving off all of the
hair on his legs, belly, arms and armpits. He wasn't as hairy as some men
she had known. Matt remained calm and quiet as she worked on him.
Stephanie could not have asked for a better client. Matt appeared to have
already shaven his face and he had already stated that he did not want his
pubic area shaved, so after his armpits were done, Stephanie was all done
with the shaving part.
"Now, go ahead and hop out of the tub and dry off," she instructed,
as she laid the razor down on the side of the bathtub.
Matt climbed out of the tub onto the bathroom floor and took a towel
from Stephanie and began drying himself off right in front of where
Stephanie was still kneeling in front of the tub. Matt's cock and balls
were bouncing wildly practically right in Stephanie's face while he was
drying himself off. Stephanie had to fight the nearly irresistible urge to
lean forward and start furiously sucking that luscious cock of his. But
the agency had rules that she must obey, so she worked as hard as she could
to keep her raging hormones in check. As a guy her sex drive had always
seemed pretty low, which had continually annoyed and frustrated her
ex-girlfriends- when she actually had one. After taking female hormones
and crossdressing full-time, her sex drive seemed to have shot through the
roof for some reason. Maybe her low sex drive was really just a product of
the fact that she simply wasn't meant to be a guy for the rest of her life.
"What's next," he asked, as he finished toweling himself off.
"Next, I'll be slipping on a nice pair of panties," said Stephanie,
as she pulled out a pair of hot pink micro fiber panties out of the
container. "Real women don't war briefs OR boxers," she advised Matt.
Matt slightly lifted each foot off the ground one at a time so as to allow
Stephanie to pull his panties up around his legs and then around his
wonderful looking "package".
"Wow," exclaimed Matt as Stephanie finished securing his panties.
"Those DO feel a LOT more comfortable than my briefs!"
"Yeah, they sure do," agreed Stephanie. It had been several years
since Stephanie had stopped wearing men's briefs but she could still
remember just how utterly uncomfortable and constraining they had been.
Once she had made the switch to panties, she had NEVER gone back to her old
boring male briefs. Stephanie could not fail to notice that as soon as she
put panties on Matt his cock seemed to harden, which in turn made her cock
get even harder. Stephanie fondly remembered how panties had made her cock
feel too when she first tried them on. She had to fight to resist the urge
to start fondling Matt's bulge but the more time she spent with him the
harder it was getting for her to focus on what she was supposed to be doing
there and the more she thought about sex. If she and Matt didn't end up
doing something after they were done here then she knew she'd have to hurry
home and take care of herself. The sexual tension was getting to be too
much for her to handle. Stephanie wondered to herself if Matt would let
her hop in the bathtub and take a cold shower so that she could cool her
"engines"?
"O.k.," said Stephanie, trying desperately to refocus her attention on
the task at hand. "Next, we'll be putting on a garter belt with some nylon
stockings," Stephanie stated as she pulled out those accessories out from
the container and began helping him get the garter belt in place around his
waist. She then helped him pull on the stockings and securely fastened the
garters to the stockings. So far so good, she thought
"Now, we'll start working on your chest and developing your boobs,"
stated Stephanie stated as she pulled out some small breast forms along
with a suitably sized bra. She thought to herself how much nicer it was to
have real boobs that responded to touch and sensation than to have to use
expensive plastic replicas that were did nothing but make it look like you
had boobs. "If you ever want to go out in public, any self-respecting
crossdresser needs to at least LOOK like they got some boobs," she advised,
with a grin on her face. "If you don't plan on growing your own at some
point that is," she added. Matt grinned back at her. "Lift your arms up
for a few minutes," she instructed. Matt immediately complied with her
request. She stood up and walked over behind him and began fastening the
back of and bringing them around to covering his "micro titties". As soon
as she had the bra fastened in the back, she carefully placed the breast
forms on both sides and situated them on his upper chest in the appropriate
areas.
"There we go. How do you feel," she asked. "They're not too
tight, are they?"
"Well, it does feel a bit weird to have stuff on my chest like
this," he admitted. "But I think I can still breathe, thanks," he added
jokingly.
"Good. Now, I think we'll go ahead and get you a top on," Stephanie
stated as she slid a red halter top over his head and pulled it down to his
waist. Stephanie observed that the clothing they had purchased for Matt
fit quite well on him so far. The measurements that they had been given
for him looked like they were pretty much on the mark.
"Now, time for the skirt," stated Stephanie as she pulled out the
accompanying dark red and orange skirt out of the container and pulled it
up onto Matt over his garter and panties. Matt was now really beginning to
lose any appearance of being "Matt".
"Do you want your face painted," asked Stephanie, getting ready to
do the all important job of make up.
"Yes please, Matt answered.
"O.k." Stephanie scanned the room for a chair but couldn't find
one. The closest thing that she could find was the toilet but of them
would need someplace to sit as well. "Do you have something we can both
sit on around here," she asked.
"I actually do have a couple of chairs in another room that I can
bring in here," Matt replied.
"Go grab them and bring them back in here. Doing makeup standing
up is going to be torture for me having to stand up the whole time and,
frankly, it would be a lot easier with us both sitting down somewhere,"
Stephanie advised.
"O.k. I'll be right back," Matt stated, as he scampered out of the
bathroom and out into the hallway. A couple of seconds later, Matt hauled
in a couple of folding chairs and set them up on the bathroom floor facing
each other in front of the sink and toilet. Both of them proceeded to sit
down. They weren't the most comfortable chairs but they were better than
nothing for Stephanie. Stephanie reached over to grab the makeup and
supplies from the container.
Stephanie proceeded to carefully apply makeup to cover up Matt's
"five o'clock shadow" and then applied some light eye shadow to his eyes.
Finally, she applied a light coat of ruby red lipstick to his lips.
Stephanie was a pro with makeup nowadays but remembered how clumsy she had
been with it when she first started trying to do it. Thankfully, Matt was
being an extremely cooperative client so far and was proving to be very
easy to work with although Stephanie noticed that Matt only had a small
mirror hanging in the bathroom and that it would probably be difficult for
Matt to see the full results of his transformation once they got done.
"Can I offer some friendly advice for you," Stephanie asked kindly to Matt
as she continued working on his face.
"Sure," Matt replied, trying hard to be careful with his facial
movements so that he didn't mess up Stephanie's handiwork.
"You need to get yourself a nice full length mirror if you plan on
crossdressing more regularly- to help you make sure you're doing your
makeup correctly. Actually, I'm not sure if you could do it well with
anything less than a full-size mirror like the kind they have on some
dressers," she added.
"O.k.," replied Matt. "I'll be sure to remember that."
"Good," stated Stephanie, as she finished up the work on his face and
breathed a sigh of relief. "Well, we're all done with your face." She
provided Matt with a handheld mirror that she dug out of her purse.
"Wow," exclaimed Matt. "My face looks lovely," he said, admiring
his newly feminine-looking face. "I can barely recognize myself," he
exclaimed excitedly.
"Well, that's the whole point of this," reminded Stephanie. "If
you still looked like yourself, then I would know that I haven't done a
good job on you so far," she teased. "I think that you look marvelous all
over but you might want to wait until we're all done so you can get a
really good view of the new you." She shot a quick glance at the container
to see what was left. "We seem to have at least one really important item
to add before your transformation is complete," Stephanie stated, as she
reached into the container for that one final item, his wig. Susan had
picked out a simple but stylish long-haired reddish-brown hairpiece for
Matt. It came with a wig cap, which Stephanie carefully placed on Matt's
head. Then, she carefully pulled the wig on his head over the cap and
covered the rest of Matt's hair with it. She took a couple of minutes to
arrange the hairpiece carefully on Matt's head. He brushed a couple of
stray hairs carefully out of his eyes.
"There. We're all done," exclaimed Stephanie, despite the fact
that she had a mysterious nagging feeling that she was leaving something
out but couldn't quite place it.
Matt started to get up from his chair. Of course, Stephanie
suddenly realized that she had forgotten his heels!
"Oh," exclaimed Stephanie suddenly. "There is ONE more thing that
I forgot!"
"What," asked Matt.
"Your high heels, of course," stated Stephanie. "I can't believe
that I forgot to put them on."
"Oh yeah, right," replied Matt. He felt a bit sheepish himself. He
had paid for them, after all.
"Go ahead and sit down again and I'll get them for you," instructed
Stephanie, as she grabbed the heels from the container. She proceeded to
carefully slip them on Matt's feet. Susan had made sure to get extra wide
heels for him. Stephanie had to wear extra wide heels as well. Although
she considered herself a woman in nearly every aspect there was no getting
around the fact that she still remained biologically male in at least some
aspects- such as her feet. Fortunately, as with everything else, they
seemed to fit Matt's feet just fine.
"O.k. NOW, we're all done," remarked Stephanie, sighing as she
collapsed in her chair. She was ready to sit back and take a breather
after working on Matt for the past couple hours.
Matt started to get up from his chair but stumbled and nearly fell
to the floor. Stephanie quickly grabbed his arm to catch him and helped
him back into his chair.
"Whoa," remarked Matt. HOW do you walk in these things," he asked
with a befuddled expression on his face.
"Oh, don't feel bad. That was almost like my first experience with
heels. I had never worn anything other than tennis shoes or loafers before
I tried on my first pair of heels," she recounted. "Just try again but
take it slowly this time," she advised. "They will just take some time to
get used to and I or somebody else is going to have to teach you a little
about walking like a lady," she remarked encouragingly.
Matt tried getting up again and this time was able to stand on his
heels without falling. He took a small tentative step towards the small
bathroom mirror to look at himself.
"Oh Stephanie," he exclaimed. "You did a fabulous job on my face
and chest!"
"Thanks," replied Stephanie. She was instantly filled with a sense
of pride in her work. "If you have a camera, I'll get a full shot of you-
if you want," Stephanie offered.
"Sure, let me get my camera from the other room. I'll be right
back."
Matt left the room again, still trying to adjust to wearing heels
and walking carefully so as to avoid falling over. After a few minutes he
returned with a small digital camera which he handed to Stephanie. She
could see that it was already turned on.
"It's all set to go. Just point and click," Matt instructed.
"O.k. Say cheese," she instructed. She turned the camera around so
that she could get a nice tall shot of Matt all "feminized".
"Cheese," exclaimed Matt, flashing a wide smile and resting his hands
on his hips in all of his newly "feminine glory"
Stephanie clicked the button and took the picture. She then passed
the camera back over to Matt so that he could review it for himself.
"Wow," exclaimed Matt. "You did a fabulous job on me. And the
picture came out great too!"
"You're welcome. I'm glad that you're happy with the results,"
exclaimed Stephanie.
"I'd say that I'm more than happy," Matt exclaimed. "I'm ecstatic,
actually," he added.
"Good. Well, my work seems to be done here. I guess I'll be
heading out", said Stephanie tentatively. She didn't really want to leave
but it was Matt's call.
"Are you kidding," asked Matt, sure she must be joking. "I'd love
for you to come downstairs with me and hang out for awhile- just us two
girls," he exclaimed.
"Great," exclaimed Stephanie, her face brightening. She was glad to
be invited to stick around for awhile.
Matt and Stephanie went downstairs together and Matt served some
them both some food and drinks while they enjoyed some pleasant
conversation together. Stephanie told Matt about her early experiences as
a tranny and her partial transition. Matt told Stephanie about some of his
experiences with coming to grips with the fact that he had always wanted to
wear women's clothing but had never had the opportunity to be fully dressed
up right. Over the course of the conversation, Stephanie began to feel a
lot like a "big sister" to Matt and thought about wanting to see if she
could continue to keep in touch with him to help support him. Stephanie
had never really felt protective like this with anybody in her life until
now. Of course, growing up as a tranny in their society, even one that had
become more tolerant in recent years, was still challenging and Stephanie
was thankful for all of the people that had helped her through some of the
rough patches in her own transition. With Matt, she felt like making up
for the support she had received by helping another transgender individual.
They finally ran out of new things to talk about after a couple of
hours and Stephanie could see that it was getting late. Surprisingly, she
was still pretty alert and Matt didn't seem that tired either. They both
just stared at each other silently. Both of them seemed unsure what to say
or do next. Stephanie thought that she noticed Matt starting to become a
little nervous.
"Is everything o.k., Matt," asked Stephanie. "You seem a little
nervous," she observed with concern.
"Oh, I'm o.k., he stated. "But there's been something I've wanted to
ask you but wasn't sure if I could," he added tentatively.
"Sure," replied Stephanie. She leaned forward and took his hand,
which she noticed was beginning to tremble slightly. "It's o.k. There's
nothing to be worried about," Stephanie said, attempting to reassure him.
"I was kind of wondering, hoping really, if you would be interested
in doing something with me tonight."
Stephanie's heart leapt. This was exactly what she had been waiting
for, of course but didn't want Matt to know that. "Sure," she replied
enthusiastically (although, she hoped, not too enthusiastically). "What
exactly would you like to do?"
"Well, one thing that I've really wanted is to be fucked like I'm a
woman? He was so nervous he had begun stammering and was bracing for
almost certain rejection. He felt like he was probably asking for too much
of an escort.
However, Stephanie wasn't fazed by the request at all. How could she
be? She had made nearly the same request herself only about a month ago
and was just as glad for the opportunity to introduce Matt to the
experience as she had once been introduced to it as well. "Matt, I would
be honored to be the one to end your anal virginity if that's what you
want," she stated, gently shaking his hand. Stephanie thought that he
seemed to be relieved by her response to his question.
"Oh, o.k.," replied Matt. He really hadn't expected her to be
o.k. with his request and wasn't quite sure whether or not he was dreaming.
"Are you sure," he asked again, just for good measure.
"If you're sure," Stephanie replied. "We'll do whatever you feel
like doing," she assured him. "Or we don't have to do anything at all,"
she added. "You're the client and we'll only do what you want to do."
"I DO want it," assured Matt. He had always been kind of shy about
asking for what he wanted.
"O.k.," stated Stephanie. "Where do you want to do it?"
"Why don't we go upstairs and do it in my bedroom?"
"Sounds fine to me," she replied. "Lead the way."
Both Matt and Stephanie walked up the stairs together with Matt in
front. Stephanie, no longer having to restrain herself, reached under the
back of Matt's skirt and brushed her hand over his cute panty-covered ass.
Matt gave a small utterance of surprise and turned around and grinned at
her. Stephanie shot a devilish grin right back at him.
Once in the bedroom, Stephanie and Matt sat down next to each other
on the side of his queen size bed and both of them stretched and removed
their heels and let their toes "stretch" for a couple of seconds.
Stephanie tossed her purse on the floor on the side of the bed. Then they
just sat there staring at each other awkwardly for another couple of
seconds. It seemed as though neither one was sure who was going to start
things off. Being the more experienced of the two, Stephanie decided to
start things off by gently grabbing the back of Matt's head with both of
her hands and giving him a passionate kiss on his lips. Matt seemed
somewhat surprised at her boldness but after a couple of seconds melted
into her embrace and soon both of them were embracing each other
passionately and their tongues were sliding all over each other inside
their mouths. Stephanie removed her hands from the back of Matt's head and
reached down with her left hand and ran it over the bulge growing under
Matt's skirt. Matt reciprocated by moving his hand down onto Stephanie's
growing bulge under her skirt. Both continued to kiss and tongue each
other. This went on for a couple more minutes before they both took off
their skirts leaving only their panties on and, in Matt's case, his lovely
garter and nylons. Matt slowly lay down on the bed. Stephanie lied on down
on top of Matt and kissed and embraced him passionately as their cocks
rubbed together through their panties.
Finally, Stephanie gently rolled off of Matt onto the bed. She then
gently unclipped the garters and tugged Matt's panties down allowing his
stiff cock to spring free. She then grabbed it with her right hand and
began pumping it. Matt moaned softly, his eyes remaining closed.
Stephanie's cock was throbbing at this point but knew that she had to take
it a little slow with her "anal virgin." After pumping Matt's cock for a
few minutes, Stephanie stopped and waited for Matt to open his eyes.
"That was wonderful, Stephanie," he quietly exclaimed.
"Thanks," she stated. She appreciated the compliment. "But it's
nothing compared to what awaits you," she hinted coyly.
"Great, bring it on," he replied enthusiastically.
"Have you ever had anything up your butt before," asked Stephanie.
"Well, I get a finger up my butt whenever my doctor gives me my
prostate exam every year of course," replied Matt. "But I've never had it
done to me just for fun. I HAVE seen pictures and videos of anal sex and
think I can manage it."
"We'll move ahead in just a moment but first, I need to get you
ready," she advised. She decided that now would be a good time for a quick
biology lesson about how their anuses are different than a woman's pussy.
"You see, an asshole isn't quite like a woman's pussy and it doesn't
produce it's own lubrication and, well, it isn't technically designed for
stuff going in, so we need to make sure that you're well lubed up, not to
mention relaxed, before I start fucking you with my cock. I'm actually
going to start with a finger or two and suck on you for a few minutes
before I move forward. It will help relax you and I think that you will
find that a finger up your ass CAN be quite a pleasurable experience."
"O.k.," agreed Matt, drawing in a deep relaxing breath.
Stephanie grabbed a condom and a packet of lube out of her purse.
Since she had been working for Creative Endeavors, Inc., Stephanie had not
been leaving the house without plenty of condoms and lube on hand. Matt's
cock was already rock hard from all of their kissing and fondling, so she
was able to roll the condom right onto it. She then dabbed some lube on
her index finger and leaned over and began gently sucking Matt's cock and
at the same bringing her lubed finger down towards his anus, gently rubbing
the lube over Matt's asspussy and gingerly beginning to push forward. Matt
winced a little as Stephanie pushed her finger in and forward and could
feel his ass muscles clamping down and trying to keep her finger out. She
took his cock out of her mouth for a second.
"Just push your butt muscles out like you're trying to poop," she
suggested. "It's the easiest way to relax those muscles so that I can
enter you."
"O.k., Matt replied. Stephanie could hear him grunting slightly and
feel him trying to push his ass muscles out as she had instructed. As he
pushed out, Stephanie found that she could finally get her finger in. She
bent it at a slight angle trying to press on his prostate gland, a source
of profound and infinite pleasure for her. Matt would soon know the joys
of it as well.
Matt began making more moans as Stephanie worked her finger in his
ass and his cock in her mouth. Stephanie added another finger while
continuing to suck on Matt's cock. Soon, Stephanie was working her fingers
in and out of Matt's ass nearly effortlessly and Stephanie could tell Matt
was really enjoying himself by the way that he began shifting restlessly on
the bed and panting and making increasingly louder moans. When Stephanie
felt that he was relaxed enough, she slowly withdrew her fingers from his
asspussy and her mouth from his cock and sat up in bed. Matt continued to
writhe in bed for a couple more seconds from the intense pleasure he seemed
to be feeling from the combination of Stephanie's sucking and
finger-fucking.
"That...was...amazing," Matt stated, struggling to get the words out
while breathing hard.
"Good, I'm glad you're enjoying yourself," Stephanie remarked. "Are
you ready for that cock in your ass that you said you wanted?"
"I think so, Matt replied, finally starting to catch his breath.
"How do you want me to go at you," asked Stephanie.
"I think I want to be fucked doggy style," Matt replied.
"Ummm," Stephanie replied, licking her lips. "Good choice," she
complimented Matt. There was nothing Stephanie liked more when fucking
somebody than to be able to see and feel the other person's ass. "Go ahead
and get yourself set up and I'll get myself ready as well.
Matt proceeded to turn over on the bed and push himself up with his
arms and knees. The top half of his body remained clothed with his bra and
halter top still on while his panties were now pulled down around his
ankles leaving his ass fully exposed. Stephanie reached over and grabbed
herself a condom and rolled it onto her hard cock and proceeded to lube it
up good. She then scooted herself up to his ass and positioned her cock at
the entrance to Matt's asspussy and rested it there patiently waiting for
the signal to start.
"Here I go. I'm going to go in really slow, remember to do what you
were doing before with my finger," Stephanie reminded him. She could
already see him flexing his ass muscles.
"O.k.," Matt replied.
Stephanie began slowly pressing her cock forward on Matt's asspussy
encountering significant resistance at first. As she slowly moved her cock
forward tentatively, she could tell that Matt was really working to let her
in. "Are you o.k.," she asked Matt, concerned that she might be trying to
move too fast for him. "Do you want me to stop?"
"I think I'm fine," he replied, grunting. "Just keep going slowly,"
he requested.
"O.k., I just wanted to make sure you're o.k.," Stephanie replied.
"Unless you have a lot of experience with ass play, the first time with a
cock is the hardest, Don't worry, though, it'll get easier, I promise," she
advised him. She reached around and gingerly stroked his cock to try to
help him relax a little bit. She could still hear him grunting a little
bit as she continued moving her cock forward but stroking his cock seemed
to help as she became able to push her cock in a little more easily. After
slowly working her cock into Matt's asspussy for a few more minutes, her
balls were finally resting comfortably on his ass-crack. She decided to
hold position for a moment and give Matt a chance to get adjusted to having
her entire cock in him.
"Wow," Matt exclaimed. He had never had ANYTHING in his butt THAT
big but it felt amazing. He could feel his cock tingling uncontrollably
from Stephanie's cock exerting pressure on his G-Spot.
"Are you ready for me to start thrusting," Stephanie asked
gingerly.
"Whenever you're ready, baby," he replied eagerly.
"O.k.," Stephanie replied reassuringly, as she began slowly moving
her cock back and forth inside his asspussy, gradually lengthening her
thrusts as Matt's asspussy relaxed more and more and Matt's grunts of pain
became moans of pleasure.
Before long, Matt began gently rocking his ass back to meet her cock.
The pain of Stephanie's initial entry seemed to have ebbed and the pleasure
provided by her cock rubbing up against his prostate was growing. Matt had
never quite experienced anything quite so pleasurable in his life. His
sheathed cock was rock hard from the anal stimulation. He began stroking
himself in concert with the rhythm of Stephanie's fucking, which added to
the pleasurable feelings he was experiencing from his prostate gland.
Stephanie stretched herself over Matt's back and began lightly kissing his
back and Matt managed to turn his head around enough for them to share a
quick tongued kiss. Soon the both of them were moving together so
cohesively that both Stephanie and Matt almost felt as though they had
become one entity united by the bliss of sexual pleasure, pleasure that was
slowly but steadily reaching that sacred sexual plateau known as orgasm.
Stephanie's cock was the first to go, furiously spewing her man cream
into her condom as she made one final powerful thrust that sent her cock as
deep as it could go within Matt's asspussy. With Stephanie's final thrust
scoring a direct hit on his prostate, Matt came next, aggressively emptying
the contents of his balls into his condom as he moaned loudly and stroked
his cock fast. Finally, both of them finally collapsed, exhausted and
panting on the bed with Stephanie initially lying on Matt's back keeping
her cock partially planted in his asspussy. After a couple of seconds, she
reached down and grabbed the base of her condom and held it in place as she
carefully withdrew her cock from Matt's asspussy. Matt winced in pain a
little as she withdrew her cock from his asspussy. Once Stephanie's cock
was out, she collapsed, panting, onto her side next to Matt, who remained
lying on his stomach and cock with his legs and arms outstretched. After a
couple of minutes of trying to catch their breath, they both headed into
the bathroom and took off their used condoms and took turns using the
toilet. Afterwards, they both got their panties back on and lay back down
on the bed together. Matt lay on his side facing away from Stephanie and
Stephanie gently sidled up to Matt and wrapped her arm around his side and
rubbed his belly and gently nuzzled his back with her nose. This had been
such an amazing experience for her and Stephanie hoped that Matt felt the
same way.
They lay together resting comfortably for about an hour before both
of them began stirring again. Matt rolled over, facing Stephanie.
Stephanie slowly opened her eyes and smiled at Matt.
"So, how did you enjoy losing your anal virginity," she asked with a
grin. "I hope that it was as pleasurable for you to lose yours as it was
for me when I lost mine."
"It was wonderful," exclaimed Matt, gently. "I really have been
missing out on a lot in terms of pleasure."
"Yeah, it's a shame that society gives people, especially guys, such
a huge complex about getting fucked in the ass when it has the power to
bring us so much pleasure."
"Maybe the people trying to shame us just want to keep the secret to
themselves," Matt suggested playfully.
"Who knows," said Stephanie, yawning and trying to wake up. "All I
know is that I don't think I can live without getting my asspussy fucked at
least occasionally." She twitched her ass as she was talking. Talking
about fucking was starting to make her horny again. "Actually, I feel kind
of sorry for those people who get so hung up about ass-fucking. They don't
know what they're missing."
"I know that I definitely want to make it part of my routine from now
on," said Matt.
"Good. There's too much stress and unhappiness in the world today.
You might as well try to grab whatever bits and pieces of happiness and
pleasure you can find wherever you can find it," advised Stephanie. This
was certainly her life philosophy, anyway.
"I appreciate your advice and help tonight, Stephanie," Matt said.
"You're welcome, I'd say that the pleasure was definitely mutual,"
Stephanie replied, thinking about how good sex with Matt had been. "Have
you given any thought to adopting a girly name for yourself for whenever
you're crossdressed?"
Matt had tried to think of a "femme name" for himself before but
hadn't been able to settle on that perfect name for himself. Maybe after
having been crossdressed and fucked would lead to some kind of an epiphany
for him. Matt thought about it for a few minutes. "I think it shall
be...Melissa," he finally said. Yeah, that sounded like a good name for
his "alternate persona.
"That sounds like a beautiful name...Melissa," Stephanie replied
approvingly.
With that, both Stephanie and Melissa wrapped each other in a loving
embrace and a deep kiss. Stephanie's cock was tingling again and as their
pantied cocks rubbed against each other. Stephanie could feel that
Melissa's cock was stirring again too. It was the middle of the night by
now and Stephanie had been planning to head on home but Stephanie changed
her mind and decided that she might just stay a little bit longer
instead...