It was time to sit back for a while and prepare for a birthday party that came up
sooner than I had imagined. The party was Minnie’s fortieth birthday. The theme was Confused.
Minnie wanted the women to turn up looking like men and the men to turn up looking like
women. I thought the *“men turning into women”* thing was going to be most interesting. When
she sent the invites out, half the crew burst out laughing and the other half looked worried about
their sexuality. She cornered those in the latter group.
*“How is this any different to any other party we have? We theme these things all the time. It is
only a bit of fun. It does not mean you are gay or whatever. I don’t allow shitty thoughts like that
and neither does your hostess, Ms KT. You may even find yourself turned on.”*
A couple of months in the planning and the evening was here. I was looking forward to a wee
blow out of sorts. Jonquil was with me. At age thirteen, she was getting very tall and in fact, she
was already taller than me. Only just though and she looked the same as I did when I was her
age, with her skin just one hue darker.
*“What are we looking for?”*
*“Clothes that will fit.”*
*“I don’t think Dad or Seth are going to have anything suitable…well maybe be a t-shirt of
Seth’s?”*
The nondescript grey t-shirt, with the giggle worthy by line…
**My Girlfriend Is With The Drummer**
*“What about legs though?”*
*“Someone will have to be big in the bum like you are…and the only person I can think of is
Stephen. Now Ma, I didn’t want to say anything but the other day when I was sorting out my
washing, I found a pair of Stephen’s jeans in the laundry. Why would he be taking his pants off in
the house?”*
*“It is not what you think.”*
*“Really?”*
I had been awaiting this moment. The point where the children would start questioning my
motives. Jonquil grew to be very headstrong much in the vein of her father.
*“Ma? I am not silly. I know you rather fancy Stephen and you two did used to date.”*
*“How did you know about that?”*
*“I love looking at old photos. I saw photos of you and Seth when you were sweethearts. But I
didn’t know you and Stephen were together like that until I came across those ones. Yet you didn’t
marry Stephen. Why?”*
*“The time was not right. I had met your father by then and your father was a better fit. He was in
the same career and mind space as me. It worked better for all of us.”*
*“You still like Stephen a lot though, don’t you?”*
*“Of course. He is a very old and dear friend and I know why his pants were here. Do you
remember that night last year when we had the pool party and I think Stephen ended up sleeping
outside in his swimming trunks?”*
*“I don’t know if I remember but go on.”*
*“Well he left them behind. He hasn’t been to the house at all this year, Quill. Sally and Stephen
broke up.”*
*“Why do my parents have such difficult lives?”*
*“We just do. Anyhow the jeans are perfect and I had better start heading for Minnie’s. Are you
going to Donna’s tonight?”*
*“Yep, a sleepover with a few girls from school.”*
Donna was Jonquil’s best friend. She was a raven-haired doll who reminded me an awful lot of
when I first met Sally. Little shivers down the spine as I got in the car and headed for the Strait
household. Frank and Seth had already left. They had a lot more preparation work than I
did. I tied my hair up rather severely as I greeted Minnie.
*“Oh you are here…come into the other room, you are the first of the girls to arrive.”*
Once we got into her parlour she produced a box of costume pieces included many a fake
beard and moustache.
*“Why on earth would you own such a bizarre box of goodies? I didn’t picture you as the dress
up fantasy type.”*
*“There was a costume place years ago that went out of business. Liquidation sale. I thought the
kids would get a kick out of it and they did but they were afraid of anything resembling hair. I
breed wee weirdoes, ha!”*
I found a fake beard that was to my liking. Minnie was a little disappointed
*“One could call you a party pooper.”*
*”Why?”*
*“Why didn’t you go with the full beard instead of this wee thing?”*
*“Given I am not a big fan of facial hair on men, I probably wouldn’t want it in on my face either.”*
*“Didn’t Stephen once have a beard and moustache…you still associated with him then?”*
*“Hardly. When I met him, his hair was long.”*
*“You are forgetting about the late sixties then. Not only was his hair long but he had facial hair by
then too. 1971 it was dead straight, no hair on the face. Then he had that almost medieval cut
and beard job a bit later on. He then had it long and beardy right up until 1976 when he shaved his
face and lopped the hair way short. I remember that moment. Wax The Floor tour…we had been doing clothes shopping. The boys went and got makeovers. Seth cut his short. So
did Frank. Blake didn’t. Tommy was certainly less woolly than he had been beforehand. Then
there was Stephen. Wow. I just about fell over backwards and I know your heart went thump.”*
*“It did, and he is going to be here tonight. It may be awkward. He hasn’t spoken to me since the
soiree last month. Admissions of almost love there and not a word since. I take it he is
still living in the apartment?”*
*“Yes, and I had a hard time convincing him to come. He was not afraid of the dress up palaver.
It was more; he wasn’t so sure about seeing you. I told him he didn’t have to feel obligated to
spend time with you. Was that okay?”*
*“Of course. Space between us is good. Especially when Sally is getting antsy.”*
*“And he should hang out with his friends. He is very good friends with both Seth, Blake and
Jamie as well…someone is at the door, hang five…”*
In fact, it was everybody else. There was suddenly a group of us all changing in the same room.
I was glad everyone was well and truly into the confused spirit. We had Minnie’s sisters
Harmony, Rhapsody and Celeste. A few of her cousins. Rhiannon, Bailey, Mary Anne – she was
Ben’s closest ally in life, Carol Carnot. Of course, Sally didn’t want to be there and with good
reason. Minnie was cheeky. When she was last at the abode, she had gone into my room and
taken a rubber dildo.
*“Hey Kitty, shove this down your pants.”*
*“It makes me look like I have a permanent erection.”*
*“Good! You look raring to go!”*
I had invited Trent and Cindy over so they could attempt to make over the boys. Not one of the
male contingents was particularly effeminate. As we filed out of our room, with champagne in
hand, out came the boys…
*“So boys, here are your girls. I make no apologies for the makeovers. I did as they wished.”*
It was right of Trent to give me caution. Oh, my. The clothing they had chosen was atrocious and
the makeup was ladled on thick. The room erupted in laughter when we realised how we all
looked. Pretty bad! Only one man stood out from the pack. Minnie leaned in close.
*“Is that a dress of yours?”*
*“Why, yes. Yes, it is! Wow. He accessorized well. He even has the belt to show off the waist!”*
*“The make up is amazing!”*
*“He has rosy cheeks, pink glossy lips and eyes framed in black eyel iner and mascara. He has
the features us girls would die for. High cheek bones, juicy lips and naturally long eye lashes. I was wondering whether I would tag along with Frank or Seth, but this definitely helped me
make the right choice!”*
The crowd dispersed, the music started and the party began. Frank was more interested in
talking to a group of young girls on the other side of the room with unrealistically huge bulges.
Like I could talk. As Seth neared me, I got the giggles.
*“Well fuck me, Seth. You make a woman I would fuck.”*
*“Do I look…pretty?”*
*“You are looking pretty damn fine and attractive I must say. Mind if I partner you tonight? My
husband seems interested in the pretty boys in the corner.”*
He took my hand and instead of his normal strong grip, it was such a slight touch. I realized he
had manicured nails. He had pink finger nails. I kept telling myself I knew Seth was a man.
Perhaps not the most masculine man despite the felt he had a nicely defined body. He still does
gym and triathlons you see. So to see him to take this girl thing so seriously was a real kick. I
began to imagine what things we could do. I felt like the luckiest guy, oops sorry, girl with him on
my arm. I headed straight for the bar and asked him to sit down. From then onwards, all we did
was drink…
I was not really interested in anybody as I was sucked into this drunken vortex of confusion. I
kept seeing Seth as a woman and not a man. Seth was not a cross dresser to my knowledge.
Remember out of all of us, perhaps Seth and I were the most honest with one another. I knew
exactly what floated his boat and vice versa and I always welcomed anything new. I did glance
around the room once or twice. Yep, the rest were pretty awful looking. For once in my life, I
didn’t find Stephen Wilcox attractive at all.. There was another part of my life slipping away. Guilt
by association.
A few hours later, I crashed through a door, in a drunken stumble.
*“Kitty…we need to find a spare room…”*
*“You will not address me as Kitty. I am Miss. I know where the guest room is…follow me.”*
I wouldn’t have pulled such a stunt elsewhere. Welcome to the Strait residence. Also a rather
large house. We had two floors to go up. The top floor had a gym, an office, the “theatre” and
the guest bedroom. I opened the door and saw the bed was made. I noticed the bottle of lube on the night stand.
*“Lie on the bed, you sissy.”*
I snarled that with quite the demanding tone. He obeyed. I started sliding my hand up his body, watching my dress inch upwards. There were those athletic legs, relatively hairless because that was more sportsmen like. I looked down and low and behold, I noticed something very familiar in patent leather black.
*“That is a rather sexy pair of heels – tell me how the hell do you manage to not topple over?”*
*“I have been practicing.”*
*“How naughty, you didn’t tell me…”*
Maybe it was the special batch of cider that circulated around this party. Notes of passionfruit
and lime. I had that brazen edge. Damn that dildo could prove dangerous. Seth, why
the fuck did you have to be so damn attractive?
*“Do you like taking it up the ass, Miss Barker?”*
It was a genuine question, it was nothing something I ever asked him. I never did ass play with
him; he only ever did it to me.
*“I do Miss. I do like the sensation.”*
*“How dare you not tell me, did you do it yourself?”*
*“Yes, Miss. But I had wished you had been there to help me.”*
Now you see, there was a particular advantage to the dildo Minnie had chosen. It was usable with a harness that more or less made it into a strap on. I had never exercised that option. Frank didn’t want anything up his backside and Seth well…I had just never asked him if it floated his boat!
*“So what are you going to do then?”*
I took off the jeans. I was surprised they hadn’t been distended out of shape by the
displacement of some six inches of personalised rubber. I hadn’t just shoved the dildo
down my pants. Minnie had also grabbed the harness and said I should wear it with that, so it
looked natural.
Natural? It had a permanent erection!
*“Oh that big boy, I can handle that though.”*
Cheeky sod I thought. When did he experiment? Obviously I was not home at the time!
The dress on Seth hadn’t quite made it past a certain point then I realised…what underwear did
he have on?
*“Can you show me your panties?”*
Oh my. He had a pair of my underwear as well. Black with a touch of a white lace and looking
most odd considering there was a rather hard cock under there. Seth was incredibly turned
on by this scenario. It was enough to make us both sober up.
*“Raise your legs.”*
*“Oh Miss, are you going to do that now?”*
*“Not quite.”*
My experiences in being the dominant were rather limited. I was more used to being a
submissive. There was all seven inches of Seth, sprung out of a lace confinement. Now – I am not supposed to suck his cock, right?
Too bad, it just looked too damn delicious. He felt so hard. So warm. I heard the coos of sweet
joy coming from Seth and I was not about to tell him off for it. As I peered up, he was looking
down at me. It was a jolt to the system. Seth was not a man at this point. Everything he did was
more female than anything else. I doubted I could ever quite look at him the same way ever
again. But best I not get him too excited…heck I was getting too excited.
*“I am sorry sissy, but as per my demands, I had to take you in my mouth. You sounded like you
were enjoying it just a bit too much…”*
*“I have never had a cock in my mouth, I can only imagine, Miss. It must be a very pleasant
experience for you. It certainly is for me…”*
*“See the underwear you were wearing…”*
*“What do you want me to do with the underwear Miss?”*
*“Well I am going to stuff it in your mouth. You are such a naughty girl. Just think, your cock was
rather excited by that pair of underwear.”*
*“You fucking dirty slut, Miss.”*
*“Do you really think you should be calling me names like that?”*
*“No, Miss, but it is true isn’t it?”*
*“I guess so…now listen to me and do as I say. If you at any time feel uncomfortable, you need to grunt for me three times. Just for your safety, okay?”*
*”Yes, Miss. I understand.”*
So I took the lacy panties and shoved them in his mouth. He looked quite silly. Silence fell and I could almost see Seth quivering. Oh whatever would I do next? I stayed silent on purpose before three minutes had passed. Maybe it was longer. I do not time these things.
*“Whatever you do, do not spit the underwear out.”*
I grabbed the lube off the night stand and slapped it all over my rubber member. I have dreamed of a moment like this, why it had not been done sooner remains a mystery.
*“Spread your legs.”*
*“Yes, Miss.”* – oh my, there be that muffled sound.
I squirted the lube onto my fingers and rubbed it around his backside. I slipped a finger in to
make sure the way was prepared for what was coming next. I poised myself for entry. It is
certainly not as easy as it looks. Angle is everything. I spread his ass cheeks and not one
complaint from Miss Barker. Oh course he was mute, he had my panties in his mouth. I
inserted my dildo into his ass. I just about orgasmed right there. Freedom suddenly become
tightened by a rather delicious backside. I stood a bit more upright.
I paused for a moment to realize what was before me.
One of the loves of my life is on his back with a strap on in his ass, a rather large hard on, gagged by underwear, with his dress hiked up, heels on, with pink nails and his make up still perfect. Banish the thought, Kitty, fuck the living daylights out of him. There were no words, as I
plunged my penis deeper into his ass. I rocked those hips. It felt so foreign yet it felt so good. I
told him to play with himself and of course, he obeyed. It proved too much. Two minutes and I
heard his teeth bite together.
Next thing I know, his load flew up and hit him right in the face.
*“Sorry to ruin your make up, Sissy.”* I took the panties out of his mouth and his radiated across the room.
*“You shouldn’t apologise, Miss. It was my fault.”*
There we were a collapsed heap on the bed. That had been incredibly potent. I looked at my
watch and it was only half ten. I had been oblivious to the music getting louder and the talk more
raucous.
*“Oh shit – Celeste has been staying in here – we didn’t get any on the bed did we?”*
*“No, just as well…we had better make the bed before we head back down…?”*
*“I think it is more important you deal with the fact you ejaculated on your own face.”*
*“I lucky I hit myself on just the cheek. I don’t want to take my make up off just yet. So how do
you suggest we make an appearance, Kitty?”*
*“So we are back to normal now…I cannot get over the sheer force of that arousal we have…”*
*“I wish I could wear heels all the time…”*
*“Why not?”*
*“Because they don’t make heels suitable for a very tall and muscular man.”*
I let out the cutest little giggle. I told him to keep the heels on and don’t he dare take the make
up until we got home. It became apparent no one noticed our absence. Such high spirits in the Strait residence. As per usual, there was Mr. Strait snoozing on the sofa along with Cindy. Minnie was looking rather dashing in a top hat and she caught my gaze. No words are needed. She knew we were up to no good. It was a pretty fantastic party!
Source: reddit.com/r/sexystories/comments/8cbufn/a_confused_party_mf_msub_fdom
I absolutely loved this thank you