My First Halloween Party


Amy was oblivious to what we were doing as she busied herself looking at things around the kitchen. I sat on the chair as I had on Tuesday and mom sat down pulling her chair in as close as she could. I rested my hand on her thigh and squeezed lightly soliciting a sly grin from her as she began to apply the make-up.

Amy went into the bathroom and I quickly gave mom a warm kiss. She welcomed my kiss but then pulled back.

"Let's just get this done. We don't want any more accidents like Tuesday night." It was almost a reprimand as her face went stern. She was obviously having second thoughts about our improper relationship. She had finished the make-up and was applying the lipstick when Amy returned. I blotted my lips on a tissue as she had shown me, and then rose as mom took my hand to present me.

"Meet Josephine," my mother stated proudly as Amy turned to look.

"Oh my God. She's beautiful," Amy muttered somewhat in awe of my transformation.

Mom ran out of the room and came back with her camera. "I have to get a picture of this," she stated snapping off shots as I placed an arm around Amy's waist.

There was a knock at the door indicating that Billy and Mary had arrived. They were going to follow us over to Jack and Diane's since they hadn't been to the house before.

"C'mon in," I yelled and Billy opened the door and came in to the house he knew so well. They were dressed in Victorian outfits that Mary had borrowed from a play she was doing.

"Hello Mrs. C. You look ravishing as always," Billy said, trying to do his impersonation of an English gentleman. Like all my friends, he had always had the hots for my mom. He walked over and took her hand, raising it and kissing it gently while his eyes feasted on the meal of breast flesh standing before him.

"Shall we go," I stated. Billy and Mary both turned to me then, a look of shock on both their faces as they realized who I was.

"Oh, this is going to be a great fucking party!" Billy exclaimed. "Sorry Mrs. C. I meant great party."

"It's OK Billy. I know what you meant. You kids have a fun time tonight and you can tell me all about it tomorrow." Mom grabbed a little black clutch and put some of her make-up in it, handing it to me, "In case you need a touch-up during the night."

We were the first guests to arrive at Jack and Diane's as planned, so we could help set things up for the party. Amy rang the doorbell and my anxiety increased ten-fold.

Diane answered the door in the sexiest little red devil outfit you will ever see. It was made of red satin with a very low cut front and must have had a built in uplift bra because there was silky white flesh pouring out the top. Diane did not have big boobs but you would never have known that looking at her in this costume. It was cinched at her tiny waist and then had a ragged mini-skirt attached that showed off her long gorgeous legs encased in the thin red nylon pantyhose and red high heels.

There was a little red tail attached to her cute butt and plenty of her upper back exposed. The requisite red horns capped her long blonde mane. She finished off her transformation from angel to devil by adding dark eye make-up and glossy, dark red lipstick. Her wide smile was proof that she was excited and ready to party tonight.

She recognized Amy right away, calling her slugger, and then Mary and Billy. "Where's Joey....," she started to say but stopped as she realized who the fourth person was.

"Holy shit!" She was totally flabbergasted and didn't know what to say.

"I love you too sweetie," I said as I walked in and hugged her warm flesh as our melons mashed together.

She started laughing and shouting, "Jack, Jack, come here. You have to see this."

Jack came into the foyer in his Groucho Marx outfit, not much of a stretch for the king of the one-liners. The wide eyebrows and moustache were glued on and he was carrying an unlit cigar. His pants were baggie and he wore a white shirt and a ragged tuxedo jacket with tails.

"Hey folks. Welcome to our humble abode. Say the magic word and you win $100. Why last night I shot a little devil in my pajamas. How she got in my pajamas is what my wife wants to know and why I had to shoot her. Hey, I'm playing here all night. Be sure to catch my show."

The words rolled off his lips like he had said them a million times, and if you ask Diane, he has. But as he looked over the four of us, his eyes fixed on my chest and then down my legs. He then got a puzzled look on his face, "Hey, where's Joe...," and just like Diane, the realization hit him like a ton of bricks.

"Oh shit. This is gonna be great! There are about twenty more people coming and only two or three have met you before. Nobody is going to know you are a guy."

"Until I start talking," I said, stating the obvious.

"OK, so we set you at the bar and you don't say anything until we get a good size group in the room. Amy and Billy will have to stand next to you so guys don't come up and try to hit on you before we are ready to reveal the secret." Jack couldn't wait to pull off his biggest practical joke of the evening.

We went to the basement game room, or what is now called a man-cave, and finished setting up tables and chairs, then brought down all the food. He had a separate beer fridge where we added our drinks to his stash. We were done in plenty of time and Billy was anxious to get a foosball game going. He and Jack were the pros so we made sure to split them up, moving Diane to Billy's team and me with Jack. I was slightly distracted staring across at Diane as she twisted the handles and leaned forward exposing even more of her glorious tits. I was praying for a wardrobe malfunction but it never came.

The game didn't take long with the pros scoring pretty much at will from long distance, though I did manage two goals on rebound shots in our 10-6 win. Billy was a little upset, but disappeared quickly as Diane gave him a hug and apologized for being a lousy player. We left the two boys to practice and headed over to the bar for our first drink.

"When I looked in the mirror, I really thought I would have no competition tonight for sexiest girl," I said to Diane. "But girl, I surrender. You are smoking hot in that little outfit."

"Yeah, well I'm not sure you've lost the contest yet. You know how men are about strange tail at a party. I bet they will be all over you whether their wives or girlfriends like it or not. At least until you start talking. Your deep voice is a dead give-away."

Mary and Amy weren't looking to happy as we joined them at the bar. We had only been there about an hour and they were already complaining that they were getting headaches. Then the doorbell started ringing and the guests started arriving in clusters. Jack's neighbors, led by Wally and Molly would be the oldest couple, now in the mid-thirties. I had played basketball out back against Wally the last time I was there. He is a 6' 3", 220 pound behemoth. Molly was an attractive stay-at-home mother of two who succumbed to Wally request that they come dressed as the cone-heads. Kind of showed their age, but they carried it off well.

They sat on the couch, with Wally eyeing me every chance he got. Molly also looked at me and whispered something to Wally who chuckled. Then about eight people from the hospital Diane worked at showed up together. One of the short, muscle-bound guys was wearing his girlfriends nursing outfit with a lot of make-up but doing nothing to disguise that he was a Man.

Wally and Molly then started doing some routine from SNL that I don't recall now, but it hit me just right and I laughed out loud.

"Holy crap, you're a guy!" Wally stammered as he jumped off the couch and backed away in fright.

"Wally, you don't remember me? Jack and I kicked your butt at basketball about two weeks ago."

"Oh dude, this is so funny. Molly and I were sitting here wondering who the slut was that didn't get word it was a costume party."

That was the icebreaker and people now started mingling and introducing themselves. A cute little chick came over and introduced herself as Missy, asking who my designer was because she thought it was a killer dress. She was openly flirting and touching my arm and hip until Amy came over and introduced herself as my wife.

After mingling for quite a while and then watching Jack and Billy dominate all comers at Foosball, Diane and her friends challenged me to a game of pool. I had to get into some freaky positions for some shots that normally I wouldn't have thought twice about, but now in a short dress, they were slightly embarrassing. The girls would blatantly stand behind me and stare at my ass as I made a shot. A few cat-calls and I started to realize how they felt when we said stupid things around them.

I was having trouble lining up one shot and Diane came over and leaned over my back, sliding her hand down my arm to guide me. She gave a little push with her hips into my ass and I got that warm fuzzy feeling going.

"That's the line. Just get a little spin on it so you don't scratch." She stayed hovered over me until I took the shot and knocked it in. "Good job partner," she said as she kissed my cheek and left an imprint of her succulent red lips as evidence.

Mary and Amy were getting a little put off at this point and said they wanted to go home. They both had headaches. Things were just getting interesting and I had no intention of leaving now after all the effort to make this outfit work. I didn't shave my legs for two hours of fun.

Billy came to the rescue, suggesting that Mary drive Amy home and he would bring me home after the party was over. He didn't drink which made him the perfect designated driver. They agreed and Diane and I walked them upstairs as Billy went back to his Foosball tournament.

We said our goodbyes and shut the storm door to watch them leave. The air had gotten as chilly as their disposition. Diane stood behind me, her head looking over my shoulder as she wrapped her arms around my waist which was hidden by the door. Her breath was warm on my neck and then she let out a little sigh. "I thought they would never leave."

She kissed my neck and I shut the main door and turned to face her. We were alone and I saw no better chance to make a move. I placed my hands on her hips and pulled her close for a kiss. She met my lips eagerly. It was a kiss two years in the making and it was everything I thought it would be. I could feel our lipstick smearing as our lips meshed and sucked, followed by tongues dueling, neither of us wanting it to end. My hands slid down the short distance to her hem and went under the skirt and felt that wonderful round ass. Her hand traveled as well coming up the front of my dress and pressing my hard-on flat against my belly.

I had started to feel like a girl at the party and now making out with Diane, I found myself letting her take charge. I popped one of her boobs out and pinched the nipple, now as stiff as the rod her hand was sliding over. I wanted suck her nipple but I knew the lipstick would leave a mark that would be hard to explain.

We had to stop when we heard voices coming upstairs, presumably to use the bathroom. Our make-up was now a mess and different body parts were sticking out so Diane quickly led me to the bathroom ahead of the oncoming herd of women. I pushed her up against the door and we continued our antics as she began to slowly pull my pantyhose down, my now throbbing manhood springing straight out to meet her long fingers as they wrapped around him.

I took the hint and rolled her hose down as well, sliding a finger into her moist slit. She pulled my cock to her and started rubbing the engorged purple head against her clit, closing her eyes and trying to breathe through her flared nostrils. I took over increasing the pressure against her slit before sliding my stiff rod into her and burying it to the hilt.

She was feverish now and she kissed me wildly and moved her hips in rhythm with mine. Our combined juices were making a sloshing sound as we fucked wildly in the bathroom. She bit her lip to avoid crying out as her orgasm started to overtake her. Her pussy clenched me tight and sent me over the edge as I spurted my hot juices deep inside her. As the euphoria drifted away, I relaxed and pulled out of her, quickly grabbing some toilet paper to sop up the mess. I handed a gob to her, knowing there was a waiting line developing outside the door.

"Tell me again why you hooked up with jack instead of me?" I asked her.

"Well honey, if you remember that first party, a question came out about what size families everyone wanted. You said you were too selfish to have kids and Jack wanted at least two kids. And with Jack's looks and mine, we should have the most beautiful children ever."

"Yeah, well I was still in college then. If I thought I stood a chance with you, I might have lied about wanting kids. You just seemed out of my league."

"What's done is done. Let's fix our make-up and figure out how to get together again later."

We cleaned up our lipstick mess and Diane had to help me adjust my wig which had really gone askew during our rut. We opened the door to some wild eyed stares as we walked out holding hands.

"He needed help going to the bathroom and fixing his make-up. Now he knows why girls go to the restroom in groups." Diane was not the least bit concerned what her friends thought.

We sat on the living room sofa talking with the soft lighting setting a romantic mood. She explained that while she was sexually attracted to me, Jack was her husband and was going to be the father of her children. She knew he had his needs with strippers and she was going to have her needs met as well. She wanted me to be part of that. I just wasn't sure I wanted to jeopardize my friendship with Jack to satisfy our mutual desires.

As the girls started coming out of the bathroom, they started joining us on the sofa and got into more girl talk. I told them I was not going to have children and ruin my girlish figure. I excused myself and went back downstairs to see what was happening. I looked for Billy but he wasn't playing foosball or shooting pool and he wasn't watching the football game. I finally noticed some movement over in a dark corner beyond the bar.

Little Missy had cornered him and had his pants unzipped. He didn't look much like the Victorian gentleman he was supposed to be with his dick hanging out his pants, but he was certainly having fun. I turned to walk away just as Jack was coming up behind me and grabbing my soft water balloon boobs.

"Hey babe. How's about you and me finding a room and playing some hide the salami?" He did a few fake pumps of his hips and waved his cigar around, staring up at me with those huge eyebrows.

"I love ya man, but there ain't no way that is ever happening." I put an arm on his shoulder and we walked over to the bar joining another bunch of his friends. We got a beer and then Wally proposed a toast.

"To Joey, the most beautiful woman here!" and raised his bottle. Bottles were clanged together and we all took a long swig off our brews.

I went over and rubbed Wally's conehead, wiggled my boobs against his arm, and gave him a kiss on the cheek. "I'll bet you say that to all the transvestites you meet."

"But I should warn you guys that the women are upstairs plotting how many children they are going to have. You may want to come up with some other distraction for them."

Wally was the first to move saying he had to get the babysitter home. A few others followed him upstairs. Jack and I looked back over to Billy who was getting his chrome polished and was close to blowing his wad in Missy's cute little mouth.

"You think he'll stay with Mary? I asked Jack.

"Yeah, he said that Mary knows he fools around with her friends and doesn't care. She wants a husband but hates sex, at least with men. Some Catholic girl thing. And she provides him with a steady access to fresh talent. When are you and Amy getting divorced?"

"I'm thinking about asking her tomorrow. Was it that obvious?"

"Yup. We all got married to young. Should've just lived together until our urges calmed down."

"I don't know about you, but I plan on having urges until they plant my cold, dead body underground."

"You know what I mean. My eyes wander and I don't have the discipline or desire to say no. I know Diane feels the same but she wants kids really bad. And you know she still has this thing for you so if you two ever hook-up, I do not want to know about it."

"I don't know if I could ever look into that cute little face of yours if I did," I lied pinching his cheek and giving him a quick peck on the lips.

"Ooh, sweet. Do you give lap dances?" he said waving his cigar around. He sniffed my neck, "Is that your mom's perfume? Ummm." He headed for the stairs to go check on his wife.

He knew it was, but it got me thinking about mom again. Diane was really just a younger version of mom and I wondered if that was why I was so attracted to her. Both were beautiful blondes with angelic personalities, but a wild side I wasn't sure about until this week. Was it really that weird that I was attracted to my mom when she was such a beautiful woman? No matter, I knew my marriage to Amy was over. I couldn't stand being around her bitchy attitude anymore.

Billy and Missy came over then and Billy asked if I could find another ride home, because he was going to take Missy home. I asked if he could just drop me at my mom's on the way and he agreed.

I called Amy but she didn't pick up until the fourth ring. "Hi. Did I wake you?"

"Uh, umm, no. I was just umm, reading," she stammered.

"Well, Billy is going to drop me off at mom's instead of driving all the way out to our house so don't wait up for me."

"OK, but tell him Mary is here. She, uh, had a headache so I gave her some of my meds and she laid down."

"Well, she might as well stay the night now. I'll tell Billy so he doesn't worry about her. I'll see you sometime tomorrow." I clicked the off button before she could reply.

When I told Billy the news, he got the biggest shit-eating grin I had ever seen. Missy smiled widely as well and then slid a hand up under the back of my dress, the feeling of her soft fingers on the nylon sending chills through my body. Billy was in for a long night.

We went upstairs to say our goodbyes even though the party was far from over. I could see the look of disappointment in Diane's blue eyes. She was sitting on the sofa and opened her legs as she looked up at me.

"You sure you have to leave so soon? We're just getting ready to play X-rated Charades." She was pouting as her hands overtly ran up her legs in invitation. Jack was getting as turned on as me as he watched her openly flirt.

"Alright. Everybody down to the basement," he said, leading the parade. "Time for somebody to say the secret word and win $100."

"Billy, why don't you warm up the car? I have to use the bathroom before we leave."

Diane smiled and quickly followed me in once they were out the door. I kissed her softly, my purple monster awakening as I forgot I really did have to pee. She kissed back lovingly as she reached under my dress to find the throbbing piece of meat she craved. Everything was slower and without the pure lust of earlier, but I knew mom was waiting at home and I didn't want another quickie.

"I'm sorry, but I really do have to pee," I said. "Can I watch?" she asked.

"You really are a little devil tonight," I stated, but walked over to the toilet. She came up behind me and lowered my pantyhose a little more, her soft hands on my hips as I tried to lose enough of my hard-on so I could piss.

She stood still behind me with her head on my shoulder as I leaned forward to point the head of my shrinking manhood towards the bowl. The tinkling started and then a steady stream as her hand came around to hold it and replaced mine. It was like a mini-orgasm as my body quivered while the fluids flowed. It slowed to a trickle and then stopped and Diane squeezed it to get the last drops out.

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byMalomar© 10 comments/ 206899 views/ 116 favorites

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