My First Halloween PartybyMalomar©
It may seem strange that my first Halloween party didn't come until I was twenty-two years old, but as a teenager I was too busy with school and sports to party very much. I had a couple girlfriends but none I was ever serious about so I didn't attend many parties that were intended for couples. I would spend most Halloweens at home helping my mother pass out candy. My alcoholic father was rarely around and Mom was great company.
Mom would actually dress up in her sexy little witches costume to pass out candy. It was like a little black dress; a tight fitting, low-cut, mini-dress slit up the sides that she would wear with thin black pantyhose. She really had the body to show it off too, and her short, blonde hair was a sharp contrast to the black dress and witches hat. Throw in the eye makeup and black lipstick, and she was one sexy little witch. It was amazing how many good, young fathers there were in our neighborhood that gladly took their kids around to trick or treat.
Even with four Halloweens in college, we never had a costume party, just horror movie marathons. Some kids would dress up for them, but neither I nor any of my girlfriends really saw the fun of it. We would rather sit back and enjoy the movies, using the scary parts as an excuse to grab and fondle each other. The rooms were always dark to add atmosphere, so no one else could see what you were doing. I even occasionally found myself groped my more than one set of hands, but would never find out who the other hands belonged to.
So after college, I got a job at a medium sized accounting firm in town and they placed me on the team for one of our new customers, a growing equipment company that had outgrown the one-man operation that had been doing a poor job on their balance sheets. Not that they were inaccurate, just always late. This cost them money because he would borrow money to pay quarterly taxes that he usually didn't owe.
So in taking over, we had to go in and work with their receivables and payables clerks to understand their system and look for ways to improve it. That's how I met Amy, a cute, thin, brunette who was very outgoing and flirty. She actually asked me out because I was so wrapped up in doing my job that I missed all the cues she was sending me. We actually had a good time that first time we went out, ending it with a pretty steamy make-out session that ended at third base. I had to go home and jerk off however since she didn't return the favor.
That should have been my first clue, but she kept being nice to me and agreeing with everything that I wanted to do. I picked the movies, I chose where we went to dinner, and I chose whose party we went to. The sex was pretty mediocre, but I figured that was just because we hadn't been together that long. Somehow I ended up proposing to her in bed one night and everything changed after that.
I came down with strep throat and even though my doctor told me to stay away from people for 48 hours to give the antibiotic a chance to work, Amy insisted that we had to go to the jewelers that night to pick out rings. I stood there with a fever of 102 while she checked out rings and I just agreed to what she liked so we could get out of there. I didn't even realize it cost me my entire savings account until the following week when I went to pick them up. I was pissed but too much of a wuss to tell them to keep them.
So as I stood in the church, waiting to go out to the altar, I told my best man that the wedding was a mistake and I should call it off. Of course he told me it was just nerves and that every groom has those doubts. And besides, all my friends and family had travelled so far to get to the out of town wedding, they would be really upset if it was all for nothing. So I ended up marrying Amy and making the biggest mistake of my young life.
The wedding was pretty much a disaster with a new priest who didn't speak much English and was also performing his first marriage ceremony in America. Half the time, no one could tell what he was saying so we would just nod when he looked at us. At the reception, he got drunk along with my father and we had to pull them apart when they started arguing about religion. Then my wife and I headed out to stay at a different hotel for the night because we didn't trust my friends to behave if they knew where we were staying.
As soon as we were alone in the room, I started to reach for her, expecting what most couples expect on their wedding night. Instead, she asked for aspirin because she had a headache. So she slept while I drank the two beers I had absconded with from the reception and watched Sportscenter.
In the morning, I once again thought I might get a little action but I awoke to find I was alone in the room. She left a note saying she went to breakfast with her friends and would be back soon. I showered and dressed in case she brought her friends back to the room. Not that I would mind if her friends came in and found me naked because they were all really cute, but I knew Amy would be pissed and one of us in bad mood was enough.
We ended up checking out of the hotel without me getting so much as a kiss, and then driving to spend the day with her family before driving back home. By the time we were home, she was too tired to do anything even though I had done all the driving. We had to be up at 4AM the next morning for our flight to Florida so once again there would be no action.
Ah, but sunny Florida should produce plenty of opportunity. Wrong again as she got dehydrated and spent most of the week in our hotel room sleeping. Having spent all that money for the trip, I'd be damned if I was going to spend my time sitting in the room watching TV. So I headed out to see the town and found a local restaurant/bar just outside the tourist area. I sat at the bar and ordered an early dinner and drinks for myself while watching a game on the bar TV.
A cute little blonde that looked like jailbait came and sat next to me and ordered a drink. Fortunately the bartender had to ask for ID and I saw her birthday made her 21 and that her name was Tammi. I started up the conversation.
"So I guess you're not a regular here either if you had to show your ID."
"Well, I've been here before but not when I was old enough to drink, at least legally," she grinned.
"So what's the place like then," I asked wondering if things picked up later. "Oh, and my name's Joey."
"Tammi," she countered. "Well," she hesitated, "it's pretty much a local bar and the guys generally don't like tourists moving in on their territory. But other than that, the food is good and the beer is cold and it usually fills up at night."
"So you're saying I should probably be moving on after I finish my meal."
She placed her hand on my bare leg, just below my shorts. "You've got some time before the regulars get here so maybe you should just enjoy the company." Her hand sliding a little higher on my leg, I placed my hand on top of hers to slow things down. I also ordered another round of drinks.
That was when she felt the wedding band on my hand. "You're married? What the fuck are you doing in here alone?" she yelled. "You here on business?" she asked in a quieter tone. She said it like it was OK for a married traveling businessman to have sex on the side, but not somebody local.
"I'm sorry. No, I'm on my honeymoon but my new wife has decided that I should be miserable so I left the bitch in the hotel room sleeping. Sorry if I seemed to be leading you on."
"Oh, sorry it's not working out like you had hoped. You seem like a nice guy." She placed her hand back on my leg and this time I did nothing to stop her approach up my thigh. She took a swig on her beer and turned her stool to face me, then placing both hands on my thighs. I couldn't help but notice that her shorts didn't cover much and were tight enough in the crotch that the stretchy material perfectly outlined her pussy.
"Well," she said again, "it looks like there are two ways this can end up tonight. We continue to drink until the gang comes in and then, even though you look like you can handle yourself, they kick your ass and you end up in jail or the hospital. Or two, we finish off our drinks and I help you with your dinner and we get out of here before they show up."
"And then," I queried. "What happens after that? I thank you for saving my life and we go our separate ways."
She reached over the bar and grabbed a fork, helping herself to some of my steak. "I think maybe we go to another place where we can dance a little, and then if we're still friends, we go back to my place for drinks." She was trying to smile as she chewed the steak, looking very much like a young child pleading their case to stay up an extra hour.
I was beginning to feel like a total asshole at this point for leaving my wife behind and openly flirting with this gorgeous young lady. But the idea caused a stir in the area her hands were fast approaching. My little head made the decision for my big head and I agreed. We finished up our drinks and left half the meal on the plate before heading out.
Tammi took us to a little spot nearby that was more upscale and had a slightly older crowd. We were slightly underdressed for the place, but no one seemed to notice or care because she looked that good in those tight, white shorts. We were able to get a table in the back and I got drinks while she freshened up. They were dimming the lights to get ready for the band just as she returned. Her "freshening up" had included a little more makeup, including a pink lip gloss, and two extra buttons undone on her top.
She didn't have much on top, but what she had was pretty much on display because she had also decided to remove her bra, if she had one on to begin with. She plopped her tiny body in my lap facing me instead of using the other chair. She then leaned in softly placing her lips on mine as she ground that cute little bottom slowly against my burgeoning manhood. There was a faint taste of strawberry on her sweet lips as I sucked her lower lip between mine. I noticed her perfume now as well. She didn't over do it, but the odor was especially intoxicating. It was familiar, but I couldn't quite place it. It certainly wasn't anything that Amy ever used.
"So, are you enjoying your honeymoon now?" she asked with a slight sound of depravity in her voice. She was clearly getting off on stealing another woman's man and with her looks, it wouldn't surprise me if she did it quite often.
She kissed me again, our tongues mingling, waiting for my response. I answered by giving my hard cock a little shove up against her grinding crotch, my hands on her ass pulling her closer. She shot her tongue deeper in my mouth in response and then started a quick in and out movement with it, which of course got me thinking of a little in and out movement I wanted to do with her. The guilt then started creeping back in as a picture of Amy, alone in our room, started to replace Tammi.
But Tammi, sensing the sudden change in my mood, hopped off me and dragged me towards the dance floor as the band started playing. The bulge in my shorts was clearly evident but I didn't care at that point. Amy disappeared from my view as I focused on this sexy nymph bouncing in front of me. The dance floor filled up quickly and we started getting pressed in to a tight group, so few people were going to notice my current state.
I caught a few glimpses of her tiny unbridled breasts as she executed some of her dance moves. It only added fuel to the flames burning deep inside me and increased my feelings of guilt. Not only was I being unfaithful to my new wife, but I was feeling like a pedophile leering at this youthful but legal nymph. Tammi could read me like a book and turned that cute little ass to me and then backed in rubbing it up and down my throbbing tumescence. She was better than any of the few strippers I had encountered in my short lifetime.
I placed my hands on her hips holding her close as she continued to grind. I had to spread my legs a little and lower myself to maintain the contact. She was almost a foot shorter than me but now my hard cock was nestled between those cute cheeks and I knew how this night was going to end. I moved my right hand from her hip and slid it under her top, only needing to go up a short distance to latch onto one of her tiny morsels. I pinched the nipple and she reached back and grabbed my ass, directing my hips to the timing she wanted.
A slightly older couple that had been dancing near us separated with the short, muscular guy moving in front of Tammi and the well built redheaded woman moving behind me. She started rubbing her ample bosom against my back and then reached a hand around to openly rub my cock. Our dancing started to slow now as it became a more overt sexual act than a dance. The redhead was kissing the back of my neck and her boyfriend was making a play on Tammi, trying to get her in a lip lock.
We broke apart as Tammi kissed the guy back and the redhead moved in front of me pressing her red lips to mine, her hand still working my bulging crotch. I could feel the moisture oozing from my cock and soaking my briefs. It wouldn't be long before a wet spot was going to show up on my shorts. I slid my hands over her round rump and then felt a rather large, powerful hand on my shoulder.
"C'mon folks. A little early for this kind of action. Why don't you take it outside." The bouncer was a tall, muscle bound brute that I wouldn't have messed with no matter how screwed up my head was. I reluctantly let go of the sexy redhead, laughing as Tammi came back into my arms. "Guess we better leave," I suggested. We quickly ran back to our table and finished up our drinks and headed for the door. I could see the redhead looking around but I was content with the hot little number holding my hand. Once back out in the hot, humid night air, we ran back to my car and climbed inside. I started it up and cranked the AC on high as Tammi slid into my lap.
We kissed hungrily, tongues dueling while she fumbled trying to get my pants undone. I pushed her top up to get at those little morsels that had been tempting me on the dance floor. They were just tiny hillocks with large firm nipples, but they were the sexiest tits I had ever seen. I latched onto a nipple just as she released my blood-engorged cock from its tight confines in my shorts. It was dripping with lubrication and Tammi smoothed it up and down my hard shaft.
I slipped a hand inside her tight shorts realizing there was no way to get them off of her without her getting off my lap. I quickly found her slick crevice and moved my middle finger between the moist lips. It easily slid inside her while my thumb found her clit and started to apply pressure.
"Oh fuck!" she moaned, wrapping her arms around my head as I nibbled on her stiff nipple while continuing to work her dripping slit. It only took a few seconds and she was convulsing in orgasm, her pussy clenching my fingers as she groaned in my ear. I held my hand in place until her breathing began to return to normal, then slowly began to remove it as she nibbled on my earlobe. We kissed again, a slow warm kiss of lovers replaced the hungry kisses from just minutes ago.
She slid off my lap without saying a word and then bent down engulfing my slippery manhood deep into her throat without even gagging. Amy had refused oral sex and the girls I had in college never managed more than half its length, so this was an entirely new sensation for me. She came back up and swirled her tongue around it, lapping the salty sauce that dripped out before sucking the head back between her moist lips. Her tongue once again swirled around the head while it was inside that inviting cavern. She could feel my cock begin to swell as the cum boiled from deep within me and she once again did her deep throat trick and swallowed me whole.
I shot load after load down her throat as my body tingled from head to toe, my breathing now stopped as my brain focused on enjoying every pleasurable second of the most intense orgasm of my life. She sucked voraciously as I continued to spill my seed down her throat and into her flat little belly. My body was a quivering mass of jelly as the high slowly retreated from my brain and I came back to Earth. I felt no guilt this time, visions of Amy the furthest thing from my mind.
Tammi was back in my lap now, kissing me softly. "How's your honeymoon now, big guy?" she smiled.
"It's getting a lot better. I hope it doesn't end too soon." The afterglow of my intense orgasm washed away any feelings of guilt I might ever have had. I hoped Amy was miserable, sitting alone back in the room. It was probably going just the way she had planned except that I didn't stay in the room and sink into depression with her.
"Hey, Joey. Why don't you let me drive and we'll go back to my place." Tammi's soft inviting smile was too hard to resist. Her child like appearance was more of a turn-on than I would have ever expected.
I had wanted a honeymoon to remember and it seemed that Tammi was willing to give me that. A voice in my head started singing an old Beatles song, "Baby You Can Drive My Car" and my mind was made up. I slid from underneath her to the passenger side and I was on my way to Nirvana.
She had a nice apartment and the sex was certainly memorable as we did it standing up, laying down, her on top, doggie style, and she had the sweetest tasting pussy this side of heaven. But it was nearing midnight and I knew I should get back to my hotel room. Tammi was very understanding and we did it one last time in the shower to remove lingering odors or perfume. When we finished, we swapped secret email addresses and then I lifted her naked body up against my clothed body for a final kiss of her succulent lips.
When I got back to the hotel, I made sure to stop in the lobby bar and have another beer so Amy would think I had just been out drinking all night. It seemed to work as she complained about my beer breath as soon as I entered the room. I told her she could bitch at me tomorrow, removed my clothes, and slipped my naked and exhausted body between the sheets. I was asleep in a matter of minutes and I'm sure there was a smile on my face.
Amy and I did have sex again a couple days after we got home. She apologized for being a bitch and was even tolerable for about a month before slowly turning back into a bitch. I am giving you this background so you will understand my frame of mind in the days leading up to the Halloween party. *************************************************
"A costume party? Really?" I was very skeptical as Amy approached me about the party.
"Jack and Diane are your friends too. And Bill and Mary are going. Stop trying to be such an adult and have some fun." Amy was telling me to have fun. She didn't know the meaning of the word.
"Fine, fine. Costume party it is. Any idea what we should do about costumes?" I asked.
"Well, I was thinking we could do the gender swap thing. I could wear your softball uniform and we could find a dress for you. With your cute babyface, we could dress you up so no one would know you are not a woman." Amy had a rather serious look on her face, like she was already imagining me in a dress and enjoying dominating me even more. It wouldn't be much of a gender swap since most of our friends already knew she was the man in the family.
"Alright, but you have to get me a dress that fits. I am not going out shopping." I then headed out for my golf date and never brought up the subject of the party. Fortunately, I rarely played golf with Jack or Bill and my normal foursome wasn't part of the crowd my wife and I hung out with. I played terrible that day, struggling just to keep my score under 90, but I just couldn't focus as I steamed about having to dress as a woman.