Chances Are Chapter 18
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"Hmmm, so this woman you saw. Was she attractive?" Jennifer, my
therapist, said.
"Oh yeah, she was about 5'8", 140 lbs. Long dark hair in a ponytail.
Blue eyes. She was wearing this white short-sleeved top, full pink
print skirt and white heels," I said. "I couldn't take my eyes off her
as we walked up the steps from the train."
"What do you mean 'full skirt'?"
"Not a mini. It came down just about knee length and kind of puffed
out, instead of clinging to her legs."
"Oh." She looked at the clock. "Our session is over. I'll see you next
week. Oh wait...can we make next week at 7:30, instead of the usual
1:00?"
"Sure," I said. "Is there a problem."
"Oh, no, I just have another patient who asked for a lunch appointment.
If it's a problem, I'll tell her no."
"No problem. Just curious. See you next week."
Jennifer had been my therapist for eight years, since before I got
married. I'd been having marital problems for about a year. I began
feeling like Jennifer was getting frustrated by my complaining. I kept
expecting her to say, "Shit or get off the pot." But therapists never
do that. I once asked her if she was annoyed, and she gave one of those
classic therapist answers like, "Well, do you think I should be
annoyed?" I guess that something you learn in training - "Always answer
a question with a question." Anyway, for the past few weeks, we'd been
talking about what life would be like if I left my wife. She asked me
to fantasize about people I saw on my way to work. I actually found it
liberating to imagine picking up someone on the train. Realistically,
it would never happen. It takes a certain alpha male type to do that
and I, unfortunately, am not that guy. Still, it was kind of cool to
imagine myself working my magic on the people I saw.
The next week, I arrived at Jennifer's office at 7:30. The receptionist
wasn't there, so she buzzed me in.
"Where's Cheryl?"
"Oh, she gets off at 5:30. It's just me," she said. "Come in."
I looked around the room, and saw a garment bag hanging from the coat
rack. "Oh," I said. "Do a little shopping?" I was just making small
talk.
"Sort of," she said, as she unzipped the garment bag. "This is for
you."
When she opened the bag, I saw a blue sheath dress. It appeared to be
slightly higher than knee length, and had white piping around the
collar and hem.
"Uh, excuse me?" was all I could stammer. "What do you mean, 'for me'?"
"Strip," she commanded, her tone becoming stern. "This is for you, and
so are these," she said, handing me a Victoria's Secret bag with a bra,
panties and stockings inside.
"What the hell is going on here?" I yelled. "What the fuck are you
trying to do?"
"Look," she said flatly. "We've talked about your crossdressing
fantasies for months. But something always seems to hold you back. You
once asked me if I was annoyed. Well, I am. For you. You need to do
this for you. And for me. It'll help the process."
I began to strip. I know this seems like I gave in too soon. But,
secretly, I had always fantasized that Jennifer would lead me to this.
Not in a dominatrix kind of way. More like a helpful friend or older
sister.
"Could you at least turn around?" I asked. "This is kind of
embarrassing."
She laughed. "I think we're kind of past that, don't you? You've bared
your soul to me. I would think your body wouldn't be an issue, at all."
I stripped. My cock shrank to nothing in abject fear.
"So, put on the bra and panties first."
I fumbled with the bra. I could never do it smoothly with the few women
with whom I had been, and this was a lot more nerve racking.
"I guess you won't be applying for a job with a bomb squad," Jennifer
said with a smile.
I turned angrily on her. "I'm glad this is so funny to you. Really
professional."
She came over and began adjusting the bra. "I'm sorry," she said,
putting a hand of my shoulder. "I saw you were tense, and was trying to
lighten the mood. You're right, though. I crossed the line, and again
am sorry. 38 chest, though. I was right."
"Well, if this ever falls through, you can get a job at a bra store. Or
maybe guessing weights at a carnival."
"OK, now for the stockings. Sit down, and let me show you how to put on
stockings." I sat.
"First, ball the stocking like this. Then point your toe towards me,"
she said and began slowly running the stocking up my leg. My cock began
getting hard.
She glanced at it. "Calm down, that's not what this is about, Steve.
Besides, I'm married."
Well, my cock inexplicably complied. It must have been that older
sister/mother thing I had developed with her. "Stand up," she said.
"Let me put these in," she said, taking out a set of silicone bags and
slipping them in the bra.
"What are those?" I asked.
"Breast forms. You surf those websites, and you didn't know what these
were," she said, raising an eyebrow.
"I thought that's what they were. I just wasn't 100% sure. So what size
am I?"
"D cup. With a 38 chest, you really couldn't be much smaller. Now, put
on the dress."
I stepped into it, and slid it up.
"Put these on," she said, handing me a pair of black slingback pumps
with a 3" heel. They were a little tight.
"How did you guess my size," I asked.
"Just lucky," she said. "Stand up." I stood up "Perfect," she said. "Oh
wait, one more thing," she said, pulling out a tube of lipstick. "This
will complete the look," she said.
"Maybe not. I think Beth will notice, don't you?"
"Don't worry," she said with a grin. "We'll take it off before the end
of the session. Now look at yourself," she said, pointing to a mirror
on her door. "What do you think?"
I looked at myself. "I look like a guy with tits wearing a blue dress
and lipstick."
"That's it? Anything else?"
"I like the dress."
"Why?"
"It's a good length. Very classic looking. With the breasts, it falls
right too."
"Hmmm," she said. "Anything else?"
"The heels."
"Why?"
"They make my legs look longer, and give them a nice shape."
"You do have nice legs, Steve. Most women would kill for legs like
that."
"Boy, thanks. You sure know how to turn a guy's head."
"You pointed it out. Not me. What's your name?"
"Steve?"
She sighed in exasperation. "You know what I mean."
"Ummm, Jennifer?"
Again, she sighed. "PRO-jection. Try again."
"Jessica," I said. "I always liked that name."
She looked upward. "Good. Well, Jessica, would you like to begin our
session?"
"Yeah."
"Girls don't say, 'yeah,' they say, 'yes, please.' Would you like to
begin our session?"
"Yes, please."
"Well, Jessica," she said, going to the door, "I have a surprise for
you. Tom, come here please."
In walked a 6'4" brown haired, green-eyed guy with a good build. You
knew he was extremely well built, because you could see it through his
shirt. "Jessica, Tom. Tom, Jessica," Jennifer said, with a leer. "I'll
be back in twenty minutes," she said, walking out the door.
"Whoa, Jennifer," I said. "What the hell's going on here?"
"You and Tom can talk," she said, closing the door and leaving.
"Uh, look, Tom," I said, backing up against a wall. "I don't know what
Jennifer told you, but, uh, nothing personal, I'm, uh not interested
and, as you can see, I'm a guy, and..."
He put his finger to my lips. "Shhh, I know who you are. You don't. But
I do. And I like a girl with something extra." He began unbuttoning his
shirt. His shirt hadn't done him justice. He had the most gorgeous set
of six-pack abs I had ever seen, and his arms were perfect. Muscular,
without being cartoon-like.
"What the hell are you doing," I said weakly. "I said I wasn't
interested..."
"Really?" he said, with a wink. "I can't help but notice you looking at
my stomach. Do you like it?"
"It's, uh, very nice. Do you do crunches, or situps, or..." I began
babbling. I averted my eyes downward. I tried not to look at the bulge
in his pants, but it was kind of hard to miss.
"Yeah," he said, "You're not the least bit interested," he said,
pinning me up against the wall. Even in the heels, he was still 2"
taller than me.
"Hey, stop. I'll hit you," I said, as he thrust his tongue in my mouth.
"Mmm," I moaned, kissing him back. He put a hand under my dress, and
began massaging my thigh. I don't know what I was thinking, but I began
playing with his abs. I had wanted to touch those abs from the minute
he walked in.
"Still not interested?"
"Shut up," I protested, as he moved his hand from my thigh to my
crotch.
"Oh, yeah, Jessica," he smirked, "I can see how uninterested you are.
Why don't you show me how uninterested," and he began kissing me again.
A gay friend had once told me you hadn't lived until you'd been kissed
by another man. He was right. My hand moved from his abs into his
pants.
"Ooooh," I said, playing with his cock. "Can he come out to play?" I
said, unzipping his pants.
I pulled down his briefs, and an 8" cock sprung out. My throat got dry
and tight and my pulse began racing. My mind said, "Run," but my body
wanted to stay. I started running my hand all over it, and began to go
to my knees. Tom stopped me.
"Hold on," he said. "Let's go slowly. Let me show you what I can do
first," he said, unzipping my dress. It fell to my ankles. "Now, lay
down to the couch," he commanded.
I laid down on the couch, and he climbed on top of me. He began playing
with my breast (forms) through the bra. Even though they were fake, I
swear I felt my nipples getting hard. "Please, Tom, please let me touch
it."
"No," he said, "I'm going to please you and then, and only then, will I
let you please me," he said. He moved his hands down, and began
massaging my ass while kissing my inner thighs. I was shuddering.
"Try not to cum," he said gently. "It'll be that much better, if you
wait. Now, roll over."
I did as he said. He began massaging my back. I never liked massages.
They made me more, not less, tense. But, something about his strong
arms made me melt. "Mmmm, that feels so good," I whispered. Suddenly, I
felt something rubbing against my ass. He began moving his cock around
my ass. Beth always liked when I did this. I never understood why. Now
I did. The feel of his cock through the satin panties was unlike
anything I had ever experienced. It was forceful yet gentle. I kept
moaning and whimpering.
"Well, clearly, you're still uninterested," he said.
"Shut up, and do it faster and harder," I said. He complied, thrusting
harder and faster.
I couldn't hold back any longer. I began making high pitched squeaks,
"Unh, oh, g-d, yes..." I came, but it felt more deeper than any orgasm
I had ever had. I felt it in the pit of my stomach. Tom stuck his hand
in my panties, and came up with a finger full of cum.
"Lick it," he said. "I want you used to the taste." I gladly licked his
finger, running it in and out of my mouth.
"Now," he said, with a devilish grin. "My turn to be pleasured. Or is
it yours...Jessica?" He straddled my face so that his cock was looking
me in the eye.
I still felt like I should run away. But, I couldn't. Instead, I cupped
his balls in my hands and began massaging them. "Oooh," I said, "Can I
play with your balls, little boy?" After a minute, I said, "Let me get
up. You sit right there." I got on my knees, and stared directly at his
crotch. I thought I'd go blind, like if you look directly at a solar
eclipse. Instead, I began taking him little by little into my mouth.
"Mmmm," I mumbled, taking him deeper and deeper each time. After what
felt like an eternity, I felt his cock shudder. Before I could move
away, I felt him shoot his load into my mouth. At first, I gagged. But,
then, I began greedily drinking it in. After he shot his load, he
pulled out. He stood up, pulled up his underwear and pants and began
buttoning his shirt.
He opened the door, and said, "Okay, Jennifer, we're all done now."
Jennifer walked back in, with a huge smile. "Thanks, Tom."
"Thanks, Jennifer." He leaned over and kissed me on the mouth. "Thanks,
Jessica." He walked out, and closed the door.
"Put your dress on, and let's talk," she said.
I put the dress on and sat down. "What the hell just happened?" I
demanded.
"What do you think just happened?"
"No offense, Jennifer, but cut the therapist-speak. I come for my usual
session, and you force me into a dress and next thing I know I'm being
assaulted by some guy."
"Force. That's an interesting choice of words. Did I in anyway exert
physical pressure upon you?"
"Well, no."
"Did I threaten to falsely accuse you of a crime?"
"Of course not. Where are you going with this?"
"I'm just questioning your terminology, Steve."
"Well, I mean, you're my therapist. You know I trust you implicitly and
I just thought that maybe if you thought this would be a good idea,
then..."
"So, if I told you to jump off the Brooklyn Bridge..."
"Ha ha," I said flatly. "I know we've talked about me seeing you as a
maternal figure, but that's a little much..."
"Fine. Let me ask you another question. What kind of dress is that?"
"A sheath."
"Sheath. Yes. And tell me about the shoes."
"Black slingbacks. With a 3" heel."
"Do you think other men know that? If I asked my husband those
questions, his responses would have been 'blue' and 'black.'"
"So what? We've covered my crossdressing fantasies. What does that have
to do with this?"
"You've talked and talked about going to a fantasy facilitator. You've
told me about your fantasy of having a female friend who helps you get
dressed. I decided it was time to dress up or shut up. And, by the way,
you were right. That dress did look very good on you. Baby blue is
perfect for your coloring."
"Fine. That doesn't excuse Tom. I never said I was gay and I certainly
didn't expect to be assaulted."
"Assaulted. Another interesting choice of words."
"Oh great, this again," I said, with my eyes rolling.
"Well, Jessica," she said, eyes rolling, "I was outside the whole time,
and I didn't hear you scream for help. If you were really being
assaulted, you would have screamed."
"Do you blame rape victims who are forced against their will and can't
scream?"
"Oh please, Steve," she sneered. "Did Tom threaten to hurt you if you
screamed?"
"Um, no."
"Did you want to scream?"
"Maybe not," I said, staring at the floor.
"Did you try and hit Tom to stop him?"
"He's like 3" taller than me, at least."
"Did you try and leave the room?" When I didn't respond, she said, "Oh
yes, I see the threat. I also couldn't help but notice that, when I
came in, your dress was on the floor. It doesn't appear to be ripped,
so am I safe in assuming you took it off voluntarily?"
I blushed. "Well..."
"And I can't help but notice that the lipstick you were so worried
about seems to be mostly removed."
"OK, I get your point."
"And I didn't notice too much on Tom's face. Would I have found some in
another place, Jessica?"
"This is so embarrassing," I said, "I never thought of myself as gay,"
and with that I told Jennifer the entire story. She made me describe
every thought, feeling and sensation in excruciating detail. She
especially had me linger over my desire for Tom's abs. I told her how
much I loved touching each and every muscle in the six pack, and how
absolutely carved his chest and arms were. I told her how I hate
massages, but didn't want to Tom to stop kneading my back with those
magnificent arms of his. I told her about how I wanted to run, but got
dry mouth and a racing pulse I got when I first saw Tom's penis. It
almost felt like she was living vicariously.
"You know what's amazing to me," she said, after I finished
breathlessly. "How alive you were when you told that story."
"What do you mean?"
"When you talk about your sexual experiences with women, you seem
disembodied. Like you were physically there, but mentally elsewhere.
But when you talked about Tom, you became animated. It was like a
different person than the Steve of the past eight years."
"I don't like where this is going, Jennifer," I said, warily.
"Steve," she said, patting my hand, "I'm not judging you. But let me
offer some observations. We've been working with 'real-life' fantasies
for the past few weeks, right?"
"Right. Where is this going?"
"When you talk about women, you say how beautiful they are. But you
spend as much if not more time focusing on their clothing than them. Do
you remember what we ended last session with?"
"The woman on the stairs."
"Yes, the woman on the stairs. You told me she was wearing," as she
looked at her notes, "a white short-sleeved top, full pink print skirt
and white heels."
"I remember."
"I hate to keep going back to the comparison, but my husband would not
remember those details. He'd remember that she was wearing heels, and
if she had been wearing a short skirt, but he wouldn't remember colors
or types of clothing."
"So, your husband's not observant. Sorry for you."
"That's not what this is about, Steve. I've noticed that, even when you
talk about a woman's physical attributes, it's usually part of a
discussion of their clothing. Like, 'she was wearing a yellow shift
that really accentuated her ass. Or the boots really drew attention to
her gorgeous legs.' Quite frankly, it's like listening to one of my
girlfriends cut apart a woman we've seen."
"So what, I'm a girl? Thanks, Jennifer. That makes me feel sooo much
better."
"Look, Steve," she said sternly. "That's not what I'm saying. Stop
projecting your insecurities onto me and listen. I'm going to ask you
one question, and answer me truthfully. When you see a beautiful, well-
dressed woman on the street, what do you want? To get in her panties,
or to get IN her panties."
"Come on. What do you think? I'm married, for chrissakes. And it's not
like my parents don't have gay friends. If I was gay, I could be out.
I'm not out. Therefore, I'm not gay. See?"
She laughed. "Now, that was an extremely convincing argument. We've
talked about this before. You've told me about wet dreams you've
had..."
"Hey," I protested. "You said those don't necessarily mean anything.
I'm so glad I trusted you. Thanks a hell of a lot."
"First off, you just issued the ultimate qualification - 'necessarily
mean anything.' I've asked you to describe the guys in these dreams.
You never mention clothes and can, in fact, rarely describe their
faces. Instead, I hear about their chests. Their arms. Their penises.
And their abs. Boy, you sure go on about abs. I haven't decided what
that means yet, but you have a thing about them."
"And that's why you chose Tom. Is this a DSM-approved therapy,
Jennifer? Bringing in hunks to seduce closet drag queens?" I said
sarcastically.
"First off, Steve, try to limit the psychobabble. A little knowledge is
a dangerous thing," she said dryly. "Second, hunk, huh? Another
interesting choice of words."
"I was being sarcastic."
"Oh really? If I called Tom in, would he say you weren't satisfied with
his service?"
"No," I replied.
"Would he be lying?"
"Great," I said, with my tears in my eyes. "I was a married man this
morning. Now, I'm some kind of drag queen cock-sucking bottom. Beth
will be so thrilled. My life is over."
"No," she said, handing me tissues. "Your life is most definitely not
over. First off, being turned on by women's clothes does not mean
you're now a female impersonator. It's something that turns you on
sexually, and you should be able to find someone who lets it be part of
your sex life. You said you approached Beth about once, and she shut it
down completely. Do you think that's fair?"
"I didn't think I should force something she hated."
"Fine, do you think sex is satisfying to her?"
"We've covered that..."
"Exactly. Do you think it's fair to her to be with someone who's not
psychologically present during sex? Shouldn't she be able to be with
someone who is?"
"Well, no."
"Look, I'm not saying to go home tonight, and say, 'Guess what honey?
I'm gay!' I think you need to figure things out first."
"Great. Turn my life upside down in one session, and then tell me hold
up. That's really fair."
"That's not what I said. I think we both know how this will end, but
you don't just upend someone else's life on a one shot deal, Steve. You
need to process this, and connect with your feelings before you go and
do something."
"I know. You're right."
She looked at her watch. "I'm sorry to end like this, but session's
over. I'll see you next week. Regular time," and she left me. I began
putting on my clothes, wondering what the hell was going to happen
next...
[To be continued, if there's interest.]
Libbie
- 18.05.2022
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