It's a Christmas Obscura! Kind of.
As we get ready for the company Christmas party, I think
back to where it all started. A simple Halloween
gag. Juliette, my wife, and I thought it’d
be fun to go in drag. I was already
planning to cut the hair away that I’d kept long since my rocker days so going
to a salon and getting it styled into this femme style was no big deal. While there the ladies trimmed my eyebrows,
and put my makeup on for the party. Once
we got home I slipped into that body forming suit with the built in fake
breasts, the bigger ass and the curvy hips.
We were originally going to go as ‘Roma and Jules’ to make a
play on our names and our costumes as I was dressed like a female Romeo and
Juliette was dressed as a male Juliet. I
mean, who doesn’t love a tongue in cheek Shakespeare reference? But Juliette’s costume ended up being two
sizes too small so she just put on one of her patented little black dresses and
we went like that. I didn’t know anybody
at the party as this was Juliette’s company, but I was still surprised that
everybody just assumed I was one of Juliette’s friends. One of her female friends.
When the guys started hitting on us I was ready to shut that
down quick but my lovely bride stopped me as evidently the one hitting on me
was a big client of theirs. Mr. Tobias
Gras. I figured it couldn’t hurt as he’d
never see me again and Juliette would get bonus points with him for introducing
him to the ‘hot new chick’ at the party.
We danced, we shared drinks, and I even let him kiss me. Of course, with the body enhancers, I only
learned later that he was practically mauling my ass and tits while we made
out. In between dances with this guy, I
found a lovely younger woman named Millani to hang out with. She wanted the company as one of Juliette’s
managers was hitting on her and she wanted to avoid him.
At the end of the party Millani asked if she could get a
ride with me and Juliette. Maybe it was
the booze, or maybe it was just the idea of helping this attractive young
woman, but I agreed. I even suggested we
take her home and let her get an Uber from there. When she asked if Juliette and I were a
couple I didn’t see any reason to let her know I was the husband dressed in drag,
so I just told her that we were friends sharing an apartment. After sharing a drink or three, Millani
shared her number with Juliette and I and said we should have a girl’s night
out sometime.
The problem didn’t arise until the next morning. When we heard the knock at the door I put on
one of Juliette’s big fluffy robes to answer it. I was shocked silent when I saw Tobias there
with a big grin on his face. I didn’t do
anything to prevent him from pushing his way in as he said he was just so enamored
with me that he wanted to see me again. He
thanked his lucky stars that Juliette and I had given his sister a ride. His sister Millani Gras. On the one hand I had no desire for this man
to see me in my home as a woman. As his ‘little
sexy Roma’ from the party. But on the
other hand, I couldn’t exactly let the cat out of the bag now. I can’t imagine he’d take it well if he found
out I was Juliette’s husband.
By the time Juliette came out to see what was going on, I’d
already made him a cup of coffee and was preparing a simple breakfast. She cornered me and had me go into our
bedroom. Not to escape Tobias’
attentions, but to put my body enhancers and some of her clothes on. Per my wife, we had to continue the deception
and figure out what to do later. We
finally got him out of our apartment, fearing the entire time that he was going
to see the home of a married couple and not two friends, but only by letting
him take us shopping. We both ended up
modeling several dresses for him but I put my foot down when he wanted to see
us model some new lingerie. By the time
we got home we’d set up a pretty good story about ‘Roma’. Freelance writer, single, just out of a bad relationship
and not looking for a new one. We
finally convinced Tobias to not come back up, saying we’d see each other again
soon, but he insisted on exchanging numbers.
Just seeing his text with the three hearts put my stomach in
turmoil.
When Juliette came home from work the next day she had a
plan. It seems that Mr. Gras was indeed
very important to the company. While her
manager didn’t want her to do anything untoward, she did want to encourage
Juliette’s “friend” to continue dating Mr. Gras. He seemed to go through girlfriends quickly
and especially when they “didn’t put out” so she figured a couple dates with
him where I didn’t offer sex would have him moving on to greener pastures and
let us resume our normal lives. And as
an extra helper, he was moving his company’s headquarters in a few weeks so he
wouldn’t even be living near here. She’d
get points at work for making a client happy, and all it would cost us is me
continuing to dress up for a week or so.
It turns out, however, that we weren’t just having to fool
Tobias. Millani, his little sister,
honestly looked at Juliette and I as friends and wanted to come and hang out. The first time she came over we just hung out
in some comfy clothes… or at least they’d be comfortable if I wasn’t wearing my
wife’s fairly form fitting sweats over body enhancers… and watched some silly rom-com. The next time though, Millani didn’t call
beforehand. Juliette had to entertain
her while I quickly and quietly got into femme mode. From there on out, it just seemed logical to
stay in femme mode until this was done.
The dates themselves weren’t all bad. Tobias was kind of sexist and being on the
other end of that behavior was both pleasant and distasteful. Sure, he helped me into his sports car, he opened
doors for me, he pulled out chairs for me.
All nice. But he also ordered my
food and drinks, chose our date activities, and decided when our date was
done. All not nice. He seemed to respect clothing boundaries, but
only in the fact that he didn’t try to disrobe me. His lips found mine far more than I was
comfortable with and these new more realistic body enhancers let me feel his
hands on me… and they were on me a lot.
He was getting frustrated at the chaste nature of our dates
and his hints were overt. He showed me
at one point that he had condoms in his wallet.
Our second date ended at a bar in a hotel where he said he had a room ‘for
us’. It was on our third date that I
really screwed things up. We’d just come
out of the theater after watching that French art film. At least that’s what they called it. I guess some could call it art, but I just
saw it as a near pornographic film about a woman going down on all the men
around her. Tobias’ intention couldn’t
be more obvious when the arm draped around my shoulder pulled me in at first
for a kiss and then tried to guide my face further down. Into his lap.
He wasn’t happy when I sat back upright, but at least he respected it
and didn’t make a scene. When we both
got into his car he pulled me in for another kiss and with obvious disappointment
said that maybe we weren’t meant for each other.
It was perfect. Three
dates. Three times being this guy’s touchy-feely
girl. Three times having to kiss and
makeout with a guy over and over. But
then I saw them. My brother and his wife. They were both such gossips and if anybody
would see me under all this feminine finery, it would be them. I absolutely couldn’t let them see me dressed
up to the nines as a woman out on a date with a man. I not only wouldn’t ever live it down, but it
would also make it to my sister, my cousins, and worst of all my parents. With about half a second to consider how to
hide I made the only choice that I thought possible. This small interior didn’t have enough room
for me to scootch down so instead I leaned toward Tobias and ducked my head
down.
It wasn’t until I felt Tobias’ hand on the back of my neck and
saw his free hand undoing his pants that I realized what this looked like to
him. As he pulled out and presented his
hardening cock to me I had two options. Get
back up and let my brother and his girl, who I could hear getting into the car
next to us, see me, and probably ruin my familial life. Or cross that line that I never thought I’d
have to cross. Private emasculation or
public humiliation.
It turns out giving head isn’t that bad. Oh, don’t get me wrong, it’s B A D bad, but
it’s not like lightning struck me dead as I let another man feed me his
cock. He didn’t taste good, but it wasn’t
awful. Just musky and masculine. And while he pushed me up and down,
controlling the pace of our coupling, he didn’t even try to push into my
throat. Long after I heard my brother
and his wife drive off I got to hear Tobias’ grunts and groans and his eventual
exclamation that he was going to cum and to swallow it down. He didn’t really give me a choice in the
latter command as he held me down while he shot jet after jet of hot sticky
musky cum into my mouth and kept me there until I swallowed it all away. He even ‘let’ me clean him up and slide him
back into his pants.
I politely declined his offer to get that hotel room and
ended up crying in Juliette’s arms that night.
She tried her best to help me live it down. Understanding that while I’d do almost
anything to help her or her career, I’d never signed up to have sex with a
man. She even tried to go down on me,
but as soon as I felt her lips caress the tip of my cock the memories came flooding
back in. I couldn’t experience having my
wife give me head without reliving giving head myself. And I couldn’t exactly complain to my wife
that one of the biggest emasculating features was the fact that ‘my man’ had an
impressive cock at least twice as big as my own.
Things sped up at that point. Millani saw us the next day and said her brother
was head over heels in love with me.
Juliette heard the next day at work that Mr. Gras wasn’t only doubling
his investment with her company, he was changing his mind about moving his
company across the country. I went out
with Tobias two more times, both ending with my head in his lap and both ending
with him wanting to take the relationship further. When I ended up blowing him while kneeling
next to him he pulled my dress up enough to expose my thong covered ass to the
air. I mewled and moaned with my mouth
full of his manhood, afraid he’d find my own hidden manhood that was simply tucked
back. In the end he didn’t explore that
far down and seemed happy enough to wet his finger and slide it into my little
pucker. Yes, I got finger banged while
giving head. He even mistook my ‘extra
effort’ in felating him and my relief afterward at not being found out as
excitement, enjoyment, and proof of getting off. “My little Roma likes anal!”
While I was ready to pull my well coifed hair out, it was my
loving wife that suggested we poison the well.
At this point I couldn’t break it off with him or let him know I was
Juliette’s husband, but I could let him know I was a man. Let him get disgusted with me and break it
off. I’d simply have to embellish a bit,
saying that I was trans and very early in my transition. I’d have to play act and probably even cry
when he’d surely tell me he wasn’t interested in having that kind of relationship.
I did end up crying. Instead
of being fake tears though, they were very real. It turns out Mr. Tobias Gras, the seeming sexist
pig was not only understanding and supportive of trans people, he was interested
in continuing to date me. He even wanted
to help me transition and help me “be all the woman” that I could be. I shed more tears when he insisted on having ‘proper
sex’ with me. It turns out he can be
quite gentle, but no amount of kind words and caresses can wipe away the mental
and spiritual stain of having a man fuck me.
The next morning Juliette had to go on a company trip for a
week but promised we’d figure something out.
She suggested I hide away at home until then, ignoring my phone and any
calls from Tobias. I tried to do that,
but Millani showed up as cheerful as ever, insisting that she knew I was home
and wanting to talk. It turns out that
Tobias told her about my ‘transition’ and she was here to help. She was so adorably into this whole process
that I found it difficult to stop her.
By the end of the day she had set up appointments with a therapist and a
doctor. Milani also said she’d come
across one of Juliette’s and my hidden photos while searching for clothes I
could wear. It was our wedding photo. Frustratingly, she said she understood and
loved that my ex-wife was helping me transition.
By the time Juliette got back home I was in therapy to transition. I was prescribed hormones and upon the
suggestion of my therapist, had an appointment with a plastic surgeon ‘to help
me along’. Juliette was painted into a
corner as Tobias let it be known at work that he was impressed with Juliette as
she was helping her ex-husband transition.
Now I had a boyfriend who supported my transition into womanhood. I had a whole medical team encouraging me to
become a woman. I had a friend, sister
to my boyfriend, who was helping me become the woman her brother would
love. And I had a wife who had to help
me be that woman or not only would her career be finished, she might even have
legal troubles with lying about having a husband and sharing insurance with ‘him’.
The hormones made it difficult to think straight. They sent me into emotional storms and I
couldn’t express what my problems were to anybody but Juliette. And while she perfectly understood, she
couldn’t do anything to fix it. Thanksgiving
was awkward as all get out as we ate at Tobias’ house. It was just Juliette, myself, Tobias, and
Millani. I was still recovering from my
breast implantation surgery so Tobias was going easy on me. I knew though that there was truth underlying
his joking. He’d joke that we couldn’t
have sex… which was a relief as I didn’t find any enjoyment at having him fuck
me no matter how gentle he was… but he’d still expect me to blow him. And he joked that he couldn’t wait to use my
hormone and surgically enhanced chest for a ‘tit job’. Millani laughed as she slapped his shoulder
and said that wasn’t funny. It wasn’t
funny. Four nights later it became
reality as I held my new D cup breasts around his cock while he pumped it in
and out and watched it cum up into my face.
So now here we are in the hotel bathroom, finishing getting
ready for the company Christmas party. I
have my arm around Millani’s waist as she has her big breasts out on
display. She’s trying to find a
boyfriend of her own now that she’s set up Juliette with a guy. Juliette and I had cried together a couple nights
ago when we signed the official divorce papers.
We realized that not only was our official marriage over, but our sex
life was also over. I couldn’t get it up
any longer and she missed the touch of a man.
I approved of her going out again and said that we’d be friends forever.
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