Forfeits
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Forfeits
By Peg Thebois
I was anxious as I arrived at Gwen's house, she had asked me to come by
early to help her set up, I guess that was part of my forfeit from
losing a wrestling match to her at our party last month. Gwen was one
heck of a sexy lady, I had enjoyed grappling with her, grinding our
bodies together, it was when I pushed her down into the mount position
and I sat on top of her trying to pin her arms down that I got
distracted. It would be very easy to have sex in that position and I
let myself get carried away thinking of sex with this gorgeous sexy
woman. In the instant I stopped struggling to pin her she grabbed my
arm and started bending it back on itself, a very painful hold she told
me afterward was called an Americana Lock. It hurt so much I didn't
even know what to do at first but cry out, it wasn't until I heard her
ordering me to tap out that it even occurred to me.
As I waited on her doorstep I thought about the words we had exchanged
as we circled each other at the start of the match, "What are you going
to do to me if you win and I have to be your servant at next month's
party?"
"I saw what you did that that banana earlier," I had replied, referring
to her demonstration of her oral skills earlier in the evening. "Maybe
I will have you give me a blowjob." It went without saying a condom
would be involved. While it was not unusual for there to be sex or
kinky fun at these parties, only the regular couples were fluid bound,
and that was only with each other.
"Would you have me naked?"
"Nah, some of your sexy lingerie is hotter than being naked."
"Yeah I could enjoy having you do that," she had said as she lunged for
me starting the wrestling match itself.
It was that last part that had me thinking all day long. So I was going
to be going down on her in my underwear, that was still a highly
enjoyable prospect. I had even gone out and bought a new pair of silk
boxer shorts for the occasion. I had only stood on her doorstep a few
seconds before the door opened. Even wearing yoga pants and a tanktop
Gwen was a vision of loveliness. The top clung to her giving a vague
impression of her cute little belly and then squeezed her considerable
breasts into a veritable chasm of cleavage, and the yoga pants showed
off every curve of her thick juicy thighs and when she turned around to
show me in it framed her delicious looking ass.
I politely said high to her roommate Carly, who was also beautiful in
her own way, as I followed Gwen upstairs being drawn along by her
crooking her finger over her shoulder at me. Carly was the more
stereotypical standard of beauty, that is to say thin, but thin was not
the measure of sexy for me.
Gwen led me to her room while and closed the door. I was so excited my
heart was practically pounding out of my chest like some kind of cartoon
character. "For the first thing I want you to do as my servant, I want
you to brush my hair, while I sit at my vanity and put on my make-up."
"Yes Ma'am," I mumbled.
"Ma'am? Hmmmm, not quite, Call me Madam Gwendolyn for the rest of the
day."
"Yes Madam Gwendolyn."
As I stroked the brush through her long, wavy red hair I stole the
occasional glance at her face in the mirror as she put on her make-up.
Even guys who were not into bigger women the way I am always recognized
that Gwen was gorgeous. Her features were cute, not elfin but cherub
like; despite that there was no illusion of innocence, this girl knew
how a thing or two about sex and it showed in her flashing eyes and
mischievous smile.
I had to be careful to time my strokes so as not to pull her head while
she was doing some of the more intricate operations with her various
paints and pigments highlighting her eyes, her lips, her cheeks, I
didn't pay much attention to it though, except when she took that tube
of vibrant pink lipstick and rubbed it all over her teasing sensuous
lips. The lips I would have had wrapped around my cock if I had won
that match.
By the time she was done with her make-up she was satisfied that I had
brushed her hair thoroughly enough. She walked over to her bed and
pulled a black plastic shopping bag out from under it. "Now let's see
that you are ready."
I nodded. "I even picked up something new for tonight."
"Did you? Well let me be the judge if it will be acceptable." I undid
my pants and lowered them to show off my new silk boxers, black and
covered in little red hearts. "Hmm, they're cute I guess but definitely
not what I had in mind, take them off, and the rest of your clothes
while you are at it."
I wasn't sure what she had in mind but it only took me a moment to
remove my clothes. Now standing before her naked I folded my hands in
front of me. "As you instructed Madam Gwendolyn."
She smiled that I remembered how to address her. "Do you recall what
you said I would be wearing if you had won?"
"Yes, Madam Gwendolyn, I said sexy lingerie."
She reached into the black bag and produced something with a flourish,
"Exactly!"
She could not be serious! What she was holding in her hand was an
unfathomable concoction of red lace. Sexy lingerie to be sure, but not
something, as a man, I could ever wear.
"I took a guess as to your size, and I am usually pretty good at
eyeballing sizes."
She should be given that she works in a clothing store, but sizing or
not, could she really expect me to wear that thing?
"Come into the bathroom, the first thing we need to do is make you
smooth."
I actually stopped following her at that word. "Smooth? Like how much
of me are we talking?"
"As much as I want to be smooth, remember you are my servant." I think
I must have looked scared because she softened her tone, "Don't worry,
it will grow back easily enough. That is if you let it, smooth skin can
be very sensuous. I will leave your pubes alone, as long as you don't
forget my proper title again."
"Yes Madam Gwendolyn." I quietly sighed to myself, this certainly had
not been what I had in mind, I wasn't even really sure I could go
through with it being seen in that by our friends. But I owed it to her
and my own sense of fair play to try.
In the bathroom she handed me the lingerie in question as she filled a
large bowl with warm water from the bathtub faucet. "I will do the
shaving, trust me I have a steady hand and know what I am doing. While
I am doing that I just want you to relax, come to terms with your sexy
lingerie, I want you to look at it, study it, drink it all in until you
know that better than any other garment you own."
"Yes, Madam Gwendolyn."
It had two cups like a bra, solid fabric with lace overtop, along the
upper edge of the cups was a red ribbon and a lace ruffle and between
the two cups was a bow of more red ribbon and a small plastic heart
decorated with rhinestones. The more I looked at it the more I realized
how sexy it really was, on a gorgeous girl like Gwen this would drive me
crazy, could it possibly be sexy on me?
While I had been starting my examination she had lathered my right leg
and started shaving it, I had been aware of that but was focused on the
intricate piece of seduction in my hands. "They had so many sexy
bustier sets, I chose that for you because of it's name. It's called
'Some Like it Hot.' " She paused the razor strokes down my leg to
giggle, even I had to admit it was a little ironically funny. As she
went back to striping the hair from my legs I continued my instructed
examination of this bustier. From the cups to the waist was an expanse
of red lace supported by firm plastic wrapped in red material, and
dangling from the bottom was four red pieces of ribbon with a little
device on the end of each one. "Those are garters, to hold up your
stockings," Gwen informed me without even pausing a stroke on shaving my
thigh.
I continued turning the garment in my hand examining everything from the
pattern of the lace to the rhinestones on the heart detail on the front
to the line of eyehook closures that run the length of the back, all the
while Gwen kept shaving me: my legs gave way to my stomach, then to my
chest. I took a moment to examine the bows that decorated the end of
each garter, and the pieces attached to the top of it like a brastrap
except it was a single loop, attached at the front on both sides.
Finally Gwen finished shaving my arms and had me turn around so my back
and ass could be cleansed of hair.
Finally smooth, except for my pubic hair Gwen dumped out the water which
was cloudy with shaving cream and hair. "Now let's just get you cleaned
off, jump in my shower." She played with my hair a moment before she
took the bustier from me, "It's too bad your hair is too short to do
anything with but we have other options."
While I showered I thought over her words, obviously that meant a wig, I
had to wonder just how much money and time had she spent putting this
all together for me? Was this more than just a fun completion of a dare
for her? If so, what did she want, a relationship, did I dare to hope
for that? The shower was quick and towelling off afterward with one of
Gwen's big fluffy towels was a whole new experience with my skin
sensitive from being shaved. I had to take a bit of cold water from the
tap and calm my growing chubby afterward.
When I joined her in her the bedroom my bustier was laid out on the bed
as well as a pile of frilly lace that I would find out were panties, a
pair of thigh high fishnet stockings and a pair of vixen-like stiletto
high heels, all red to match my lingerie. She started me off with the
panties which were literally covered with layer after layer of ruffles
from the waist to the crotch, and in the center of the back was a big
ribbon bow. Then she took my bustier, my "Some Like it Hot" bustier,
and wrapped it around me, the brastrap going behind my head like a
halter. She had to fiddle a bit with the closures, around my chest
there were a couple she was concerned wouldn't do up but in the end she
got me sealed into it.
She took one of the red fishnet stockings in her hand and bunched it up,
I had seen the scene in movies many times, a sexy stocking slowly
rolling up a smooth feminine leg. Never would I have imagined it would
be my leg being gripped and caressed by the nylon mesh, and never would
I have guessed it felt even sexier for the wearer than it looked. After
the first stocking was squeezing tight to my thigh, held in place by the
taunt ribbons of the garter Gwen ran her hands up from my ankle to the
lace stocking top. I wasn't sure if it was to smooth the garment or
just to tease me with how incredible it felt the combination of nylon
tightness and skin on skin contact through the gaps.
Gwen giggled at the erection rising up from it's flaccid state as she
started to repeat the procedure with the other leg. "It looks like
someone is having a good time, at least so far, we'll see how the little
guy feels a bit later, see if he feels like showing off for all our
friends." That brought me back to earth, in the last while I had
forgotten this little game of dress-up was not just for me and Gwen, all
our usual friends would be at this party. What would they think?
I had to protest, I could not go through with this. "Madam
Gwendolyn..." I began timidly but she cut me off immediately.
"No! You are not backing out of this."
"I can't go through with this, not in front of everyone."
"You can, and you will. I know you are worried about what people will
think afterward but these are our friends. You know how these parties
get, is there a single girl who comes to these who hasn't been in her
underwear at one time or another?"
"But Madame Gwendolyn, that is different. I'm a guy, I'm not supposed
to wear things like this, it's kind of gay."
"You hush your mouth! Scott and Tim are gay, have you ever seen them
wear anything like this?"
"No,"
She pressed her advantage before I could even rebuttal, "Exactly,
therefore it is not gay. Now I want you to relax. Think for a moment
about the parties in the past, Pretty much every girl here has simulated
oral sex on something, we've seen spankings, nudity, groping, actual
oral sex, and a lot more. Now do you think negatively of any of our
friends for anything you've seen them do at these parties?"
I gave a defeated sigh. "No Madam Gwendolyn."
"Good, then that is the last I want to hear of this tonight."
I'd had to try, but as we moved to her vanity and she did my make-up now
I had to admit to myself I did feel better. This wasn't going to be a
big deal, I would feel pretty silly, and maybe folks would give me a
hard time about it, but just in that playful way friends did with each
other. Madam Gwendolyn made sure to face me away from the mirror while
she did my make-up but I did notice the colours she was using, she used
a lot of bright pink and black on my eyelids. Of course my lipstick was
bright red, with a shiny coat of gloss over top, and she glued these
enormous false eyelashes on me, it was weird actually being able to kind
of see my eyelashes out of the top of my sight.
The last touch was a curly red wig that fell to my shoulders, after
fluffing and primping that she turned me around and let me see myself in
the mirror. I was actually kind of pretty! I was definitely a man,
even ignoring the lack of breasts and the conspicuous bulge in my
panties there was no doubt this was a man's face, but it was a pretty
man's face.
By this time we could hear there were already a couple people
downstairs. Madam Gwendolyn went down first and I listened to her
address the group, "Hi everyone, I have a special guest here tonight.
She's going to be waiting on me this whole evening, if you want her to
grab you a drink or something like that feel free. Come on down,
Daphne." Daphne, a Some Like it Hot reference, at least it wasn't the
feminine version of my own name. As I descended the stairs into the
living room there was a chorus of hoots and hollers from our friends.
"Daphne, go get me a Diet Coke from the kitchen please." A couple
others called out requests as well.
That set the tone for the evening, I spent a fair bit of time running to
grab drinks or snacks, or make popcorn, or even answer the door. When I
wasn't doing that I was sitting down, beside Madam Gwendolyn as often as
I could but sometimes she would trade places with someone else. Over
the course of the evening I found another benefit of his outfit; the
girls were all expressive with their approval of how I looked in the
form of teasingly grabbing my ass or stroking my leg or other
affectionate contact whenever I walked past them. Sure once or twice I
had a guy slap my ass, but that was not a big deal it was done in
harmless fun.
The evening wore on and we reached the height of the party, that point
after everyone has arrived but before the early birds have to start
leaving. Madam Gwendolyn called me over to her from where I was
sitting, talking with a couple other girls who had stripped down to
their underwear, ostensibly to make me feel more comfortable but I'm
sure no-one else complained. Madam Gwendolyn commanded me to kneel as
she got up from her armchair to stand over me. "Alright Daphne, you've
been a great helper this evening, so you can take the rest of the night
off. But the last thing before you are done, there is still another
half of your forfeit to complete, isn't there?"
"Yes Madam Gwendolyn."
"Take off my pants Daphne, just my pants though, not my underwear."
Yoga pants were pretty easy to remove as they were just stretchy, no
zippers of buttons. I has careful in selecting my grip on he sides so I
didn't get her panties as well. I slid them down anticipating the view
of her panties and below that her beautiful womanhood that I would be
servicing. I didn't pay any mind to the fact that her panties had
buckles on the sides, it wasn't until her pelvis was revealed that I was
a little bewildered. Overtop of her crotch was a metal ring secured
with three straps, each of which had a snap on it.
She sat down again so I could slide her pants down past her feet and
off.
I just stared at the unusual underwear as Madam Gwendolyn picked up a
non-descript box from the table beside her chair, it was only once she
opened it that everything clicked in place for me. She had never
actually said I would eat her pussy. I'd said I would have her give me
a blowjob and she said that she would have me do the same. That was why
she was at that moment securing a long pink dildo trough that metal
ring, she was going to have me give her a blowjob.
I must have looked pretty shocked, and probably frightened because
everyone else was laughing, or maybe it was just the prospect of me
having to suck a silicone dick. I know she expected me to resist,
everyone would expect that, on a crazy impulse I decided to play to
everyone's surprise and lunged forward like a desperate fiend. I opened
my mouth and in an instant took as much of her cock in it as I could
fit. The laughter was now mingled with noise of surprise and a few
catcalls of encouragement, but all I really cared about was putting on a
good show for Madam Gwendolyn, his would also mean putting on a good
show for everyone else there but that was incidental to me in the
moment.
I bobbed my head up and down on her pink pole letting the tip slide
between just behind my lips and the back of my throat. I felt her hand
on my shoulder, encouraging without interfering in my efforts,
apparently I was doing well enough. I tried pushing my head further
down the pink shaft on each stroke, I could almost get the whole thing
in my mouth, I figured for some reason that would please her. At one
point I pushed too far and my gag reflex came down on the invading
material.
Instinctively, I pulled back letting her dildo slide out of my mouth as
I gulped a deep breath to steady my throat but I immediately played this
off licking at the head of her dildo, hoping no-one would notice that I
had choked on it. No-one except Madam Gwendolyn of course, she was too
close to the action not to notice. I swirled my tongue around what
would be the crown on a more realistic shaped dildo but this one was
just a smooth pink shaft, looking as little like an actual penis as it
could.
After teasing the tip for a bit I returned to bobbing my mouth on the
shaft, I could hear a few of our friends making comments behind us, all
meant in good humour of course. "He's pretty good at that." I wasn't
sure which of the guys there it was who said this as I was more focused
on my quest to take the whole dildo down my throat
"Well.. He's enthusiastic, I will give him that." This voice I did
recognize, Shay, one of the girls in her underwear I had been talking to
before being called to task to give this blowjob.
"Better than my first attempt, I would say," Tim chimed in.
"If he doesn't puke on her lap he'll do better than your first time,"
Scott replied.
I didn't notice I had slowed my strokes until I felt Madam Gwendolyn
grab a handful of my wig and shove my mouth down her cock, as far as I
could manage. "Pay attention to your own business Daphne."
I tried to mumble something affirmative but I'm sure it was incoherent
around my mouthful. I tried my best for several minutes but I didn't
manage to get my lips to touch her harness before she grabbed my hair
again and this time pulled me off her cock. She pulled my head onto her
lap and we both just sat there a moment. Our friends were clapping for
the show we put on but I didn't care. Laying there head in her lap a
emotional light took me, and I strayed out of thought and time. Stars
wheeled overhead and every moment was as long as a life-age of the
Earth.
Eventually Gwendolyn and I went into the kitchen for water and privacy.
"How is my girlfriend doing?"
If anything could have made me more elated than I had been it was that
word, 'girlfriend'. "A bit confused, I really enjoyed doing that for
you."
"Don't worry, I don't think you're gay, although you may just have a
little lesbian in you."
I chuckled. "so I'm your girlfriend now am I?"
"I was hoping so, if you want to be."
"Can I be your boyfriend too?"
"Of course, but I think it will be extra special when you can be Daphne
for me."
By way of answering her I gave her our first kiss. I melted into her
and she into me, not becoming one but entangling one another in our
arms, and legs our tongues and minds. No-one interrupted us for a
prolonged period of time and we just embraced and kissed and physically
explored one another, without letting our hands stray into naughty
places.
Eventually though someone did need a glass of water and we rejoined the
rest of the party, a couple people had already left in our absence.
When we went up to her room for me to get dressed, keeping my lingerie
on under my normal clothes, she got me a bag for my wig and shoes, a bag
which already had something else in it.
She handed it to me. "I prepared this just in case, look when you get
home."
I was glad for having a ride home, returning by bus the same way I had
arrived would have been embarrassing with my face still caked in make-up
and my wig in the bag. Fortunately I live by myself and this late I was
able to get through the halls to my apartment without meeting anyone.
I weighed whether to shower first or peek inside the bag Gwen had given
me, and decided to prolong the mystery a bit more. After I was sure
there was no hint of make-up to betray me over the next couple days, or
God forbid, at work on Monday, then I sat down to open my present.
The wig was wrapped in a mesh bag keeping it from tangling, and the
shoes were of course also on top, underneath that was a marbled school
notebook, with Daphne's homework written on it.
I opened it up to glance through only the first page was marked.
* Sunday: Sleep in on your day off.
*Monday: Practice in heels for 30 minutes
Watch make-up tutorials on youtube 30 minutes
*Tuesday: Panties to work.
*Wednesday: Guy day.
*Thursday: Hand wash panties
Practice make-up for 1 hour
*Friday: "The box"
*Saturday: Shave yourself.
Be dressed and ready to get picked up at 6:00
"The box" right before 6:00
Two mentions of a box had me curious so I dug further into the bag
finding a ziplock baggie full of make-up, obviously for Thursday. That
was on top of a bright red spandex dress, it looked low enough in the
front to emphasize my lack of cleavage and short enough to barely cover
my panties, wearing this would be nearly as revealing as "Some Like it
Hot"
The box was the last thing in the bag, a plain white box , no markings
on the outside but it rattled a bit when I shook it. I was sex savvy
enough to recognize what was in the box when I opened it, a tube of
lubricant and a metal butt plug, although I am not experienced enough to
say how large it was by the standards of these things. The base of the
plug was decorated with a bright purple plastic jewel.
Using this on both Friday and Saturday? It was pretty obvious what Gwen
had in mind, and I knew right then I wouldn't fight against anything she
wanted me or Daphne to do for her.
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