10 comments/ 168945 views/ 67 favorites My First Halloween Party By: Malomar 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. My First Halloween Party I got home just as the sun was setting and Amy was waiting, a wicked smile on her face. I knew something was up. "We found you a dress today," she touted. She was wearing jeans and a sweatshirt, her normal gear for this time of year. "Who is "we"?" I asked. "That would be me," my mom said as she strolled into the kitchen. She was wearing a tight form-fitting, white top with a white lacy bra underneath. The stretchy black pants completed the picture of the sexy thirtysomething suburban housewife, even though she was ten years older than she looked. "Oh Christ! She told you about this party?" "Watch your mouth young man." "Sorry mom." She smiled and held up a satiny black dress with white lace trim. "We got it at Goodwill. It's a waitress uniform but I can make some adjustments to make it look more sexy. I'll remove the lace border and give it a slight V-neck so you can't tell anything was removed. Here, try it on." The words came out quickly as she walked up next to me and handed me the dress, giving me a hug and quick kiss on the cheek. I smelled her perfume. A familiar odor that had puzzled me once before. It was the same perfume that Tammi had been wearing when we met in Florida. My cock started to rise and I was truly confused whether the cause was Tammi or my mother. Aside from both being blonde and flirty, they really were nothing alike. I went to the bathroom and removed my golf clothes, throwing them into the hamper, leaving just my briefs on. I stepped into the dress and zipped the back. It only went about three-quarters of the way up leaving some of my bare back exposed. It had short sleeves and the bottom was about half way down my thighs, my hairy legs fully exposed. I walked back out to the kitchen and did a little pirouette for them. "Well, what do you think? Am I gorgeous?" Amy just laughed. Mom took charge now. "You will definitely have to shave just before you leave for the party and wear some make-up. I'm not sure about the legs. Do you have any black pantyhose?" "Well mom, I generally don't wear them. And those football players you see on TV just do commercials for the money." "I was talking to Amy, Mr. Wiseguy." She said it sternly but she couldn't help but grin. "I do," Amy said as she headed off to the bedroom. "But I think he'll need queen size," she said returning to the kitchen. "Try them on Joey," mom said as Amy handed them to me. "Let's see what we've got to work with." I started to head back to the bathroom, but they both stopped me. "Jeez, just pull them on, will you." Mom said. "Here, I'll help," added Amy pulling up a chair. Amy started to roll up one leg and handed them to me and I took them and got the first leg up over my knee. They were pretty snug alright. "Stop," mom said. "You can still see the hair through the pantyhose. He'll have to shave his legs too." "Aw, c'mon. It's just a costume party. Nobody is going to be looking at the legs of a guy in drag." "Honey, when we get through with you, you could do the cover of Playboy. Amy, go get him a bra so I can make the markings and know what I have to take in and let out." "There's no way my bra will fit him. I'm a 32A. He's going to need one of yours." Mom didn't hesitate. She reached back under her stretchy white top and unhooked her bra, then did some kind of contortionist move and pulled the bra out the front. Her ample bosom pressed hard against the soft material and I watch in awe as her nipples grew in front of my eyes. Then both women took an arm as I felt the zipper come down on the dress. They took my arms from the sleeves and pulled down the front of the dress, exposing my slightly muscular but hairless chest. "My, they grow up so fast Amy," said mom, admiring my bare skin. "Too bad his legs weren't as hairless as his chest." They then proceeded to slip the bra on and pull the dress back up. I sat back down and removed the pantyhose from my one leg before they could say anything else. Mom had her chalk and pins started making marks around the shoulder areas and waist, then pinning the hem. Her hands were soft and gentle as she marked up the dress and her perfume started to get to me again, my cock slowly rising in my briefs. Her head was down at crotch level as she pinned the hem. I couldn't help but glance at her pendulous breasts moving freely inside the tight top, her nipples firmly outlined. I even noticed Amy catching quick glimpses when she thought no one was looking. Yes, my mom was a MILF of the highest order. Mom stood up after pinning the hem and stepped back to get a full body view. I was hoping my now awakened member was not pushing out the front of the dress. Amy smoothed the back of the dress, running her hands over my round buttocks. My cock gave a little lurch and again I hoped no one would notice. The more I thought about getting a hard-on around my mom, the more excited I was getting. I had to block it out. Mom and Amy stood there whispering about five feet in front of me. Then finally mom spoke up. "OK, I think I can work with this but the white bra is a no-go. I've got a black one at home he can use. And I should have some shoes back at the house that my sister left for Goodwill. She has boats for feet so there should be a pair that fit him. What are you going to do about his hair and make-up?" Amy was ready, obviously having already given it plenty of thought. "I have an auburn wig I use for bad hair days. It should fit him. But I think he'll need your make-up because my skin tone is totally different than his." OK then," mom said, taking charge again. "Let's get that off him and I can get started." She looked directly into my eyes. "Bring the pantyhose and wig to the house Tuesday night. I'll have the dress done by then and we can see how the whole outfit looks with some make-up. Call it a DRESS rehearsal." I groaned, but Amy laughed at the intentional pun. Then they were on me like housewives at a Macy's sale on Black Friday. The zipper came down and they each pulled an arm through the dress and pulled it forward and down, leaving me standing there in my briefs with my cock at half-staff and bulging against the front. "Well, that's embarrassing," Amy muttered. "Hmm, not embarrassing me," mom said, an almost hungry look in her eye. "Well what did you expect? A man has two beautiful women pawing him, nature is going to take over." I turned and walked out of the room. Mom was glowing at the compliment, but Amy was somewhere between excited and agitated and I couldn't tell which. I went back into the bathroom, pulling my cock from my briefs. It was dripping pretty good now and I spread the lubrication along my length quickly bringing it to full-staff. My heart was pounding as I masturbated while my wife and mother were on the other side of the door. I thought better of it and stopped, embarrassed and irritated at myself. As my rod calmed down, I squeezed out more lubricant into a washcloth and wiped him down, placing him back into my briefs. I heard the outside door shut and Amy opened the bathroom door without knocking. Good thing I had changed my mind. "It's OK to come out now. Your mom left. How you could you get excited with your mom in the room? Did you enjoy being a girlie-boy?", she said in a mocking tone. "I guess so," I replied, slightly disgusted with the whole situation and not willing to admit that my own mother was part of the reason I got stimulated. "Wait here a second," she said and quickly ran off to the bedroom. She came back with one of the sexy black lingerie outfits I had bought her for the honeymoon. She never wore it. "Here, put this on and then join me in the bedroom. Maybe we can both get something out of this situation." She was clearly getting into this and was more sexually alert than anytime I can remember since that first date. I pulled down my briefs and replaced them with the thin black thong, then pulled the see-through top over my head. I looked in the mirror and I looked stupid. Well, if I'm going to look stupid, might as well go all the way. I found a tube of Amy's lipstick that she didn't use often, Ruby Red, and smoothed a little on my lower lip, then mashed my lips together to get some on my upper lip. Just right, I headed for the bedroom. Amy was waiting, already naked and sitting up, wild anticipation in her eyes. She had both bedside lamps on so the room was more romantically lit then with the glaring overhead light. She waved her hand over the sheets on the near side of the bed, indicating she wanted me to lie down there. I hesitantly approached the bed, eyeing her naked form. She was an attractive woman. Her small breasts would have looked large next to Tammi's bumps, and the pink areolas were just a shade lighter than her now excited nipples. She didn't shave her pussy, but the hair was trimmed neatly. I had yet to taste her even though we had been married for six months. I lay down and she lowered herself down over me, bringing her lips to mine. The lipstick felt good on my lips and I wished that she would wear it more often, especially during sex. I heard the sharp intake of breath as her nostrils flared and she sucked my glossy, lower lip between her dry lips. She was really turned on now as her right hand roamed over the thin material of the nightie. Her right leg slipped between mine as she increased the pressure of our kiss. My swollen member had slipped out the bottom of the thong and was stretching down my thigh, which was the wrong direction as far as I as concerned. I reached down and straightened him out, pulling him back through the thong so he lay flat on my stomach. Amy was hungrily sliding her tongue into my mouth now, grinding her leg against my crotch and her pussy against my leg as she took complete control. Her hand was now up under the top, running across my bare chest, stopping to tweak a nipple now and then. Her breathing was ragged and I knew she was close to losing control. She raised herself over me now, both my legs now between hers, and lowered her pussy slowly against my now dripping and throbbing tumescence. She reached down and squeezed the head, more lubricant dripping out, and then rubbed the magic lotion into her pussy, fingering her clit as she did. She then lowered her pussy back down and rubbed it up and down the length of my hardened shaft. She was literally gasping for air now as her pace quickened. I was finally able to get my hands free and placed one on her hip to try to slow down her motions, to no avail. I brought the other hand to her breast, fingering the turgid nipple and tried to pull her down to me. She raised the nightie up to my neck and raked her fingernails slowly down my chest, a demonic look in her eyes. She kissed me briefly, and then raised her breast up to my mouth as I sucked the nipple between my lips, quickly whipping my tongue back and forth. With her body higher up on mine, her clit was now rubbing just the head of my hard cock and she quickened the pace even more. She increased the pressure until it felt like bone on bone, the rapid movements bringing on a flood of orgasmic ecstasy that I had never seen in her before. Her body stopped moving, her breathing stopped, and her movements slowed as she pressed down harder with her clit on the head of my prick. She had never let herself go like this before. Puddles of liquid developed on my belly, part mine and part hers, as she continued to cum and press her clit against my purple monster. As her breathing began to return, I lightly bit her engorged nipple which was still trapped between my lips. She started moving her hips again, sliding her slick crack the length of my swollen shaft, both of us now moving toward a common goal. I placed both hands on her hips, insistent that I control the action this time. I raised my hips increasing the pressure between our swollen organs as her breathing also increased. It never took her long after that first climax was over and I could feel it building inside her as her legs squeezed mine even tighter together. The tingling in my hungry cock was unmistakable now even though there was no penetration. Our bellies close together created all the feeling I needed as I sped up the pace. "Oh Shit!" she screamed, as another orgasm racked her body. She kept pressing down harder until I finally exploded, shooting wad after wad between our bodies, one blast hitting me in the face as she raised her upper body to increase the contact of our lower bodies. Her body was shaking as she continued to rock herself into multiple orgasms while my body quivered beneath her in orgasmic bliss. This was by far the most intense sex we had ever had and gave me some hope that maybe we could salvage our relationship. Sex wasn't our only problem, but the lack of it seemed to intensify every other problem we had. I waited for her to clean me up, or at least get me some tissues like I normally did for her. She rolled off of me and lay flat on the bed. "Make sure you don't drip that on the bed or floor when you get up. And there's some on your face too so clean that up." She was right back to her bitchy self in two seconds flat. So much for hope. I turned my head to look at her, my bliss now disappeared. I used a finger to get the glob off my chin and then placed it in my mouth and swallowed, glaring back at her. "Why do you have to be so disgusting," she muttered. So I grabbed another glob off my chest and exaggerated my motions as I swallowed that as well, a look of defiance on my face. "Oh Christ!" she said, exasperation in her voice as she grabbed some tissues and wiped the remaining goo from my body. "See, now was that so hard?" I said now looking down on her. There was still quite a bit of my spunk glistening on her belly and chest. While my manhood had started to shrink, he was not quite dead yet. I decided to try for round two. I leaned down and kissed her lightly, knowing she would taste my musky spunk. She didn't back away as I expected, but pressed back for a deeper kiss. I slid my tongue in her mouth and felt her body tense. I wasn't sure if it was excitement or her gag reflex, but she brought her hands to my body, one going to my once again burgeoning manhood. I bent down and took a nipple between my lips, tonguing it hard. I started to kiss my way down her body, stopping at her navel to lick out the puddle of juices there. Our combined spunk was all over her and I hungrily licked it from her body. Once I had it all, I continued my descent, intent on finally tasting her little snatch. But she stopped me cold, grabbing my head. "No, you know I don't like that." My anger started building. I slid my body on top of her, running my once again rock-hard rod against her belly. I moved it higher between her tiny breasts, creating my own tight little tunnel. I could feel her cringe as I rubbed the angry purple head against an excited nipple. I rose up higher and moved my monster towards her mouth, but her mouth held tight as I spread my drippings along her lips. I could see this was getting me nowhere and backed down. There was no sense in trying to fuck her, since I knew she didn't enjoy that. I placed my prick against her clit again and rubbed it back and forth. Her breathing quickened again and in matter of minutes, she was cumming again. I sat up and jerked myself off, finally spraying my second load all over her again. If her eyes had been open, she would have seen the hatred on my face. I squeezed the last drops out of my cock and then climbed off her, handing her some tissues to clean up. I stripped off the nightie and walked naked to the bathroom. I took a hot shower to remove the stickiness of our juices and the sweat from my earlier golf outing. When I came back to bed, she was already asleep, or at least pretending to be asleep. Our lines of communication were down and any hope I had of making this work were fading fast. ********************************************** Tuesday night came quickly but Amy forgot to mention she had a crafting class that night so I was off to my mother's house with wig and pantyhose in tow, having freshly shaved after dinner. Mom was waiting eagerly and almost pounced on me when I arrived. Her short blonde hair was immaculately coifed and her make-up was perfect right down to the light red satin lipstick. She had used the same perfume as always, but definitely more of it than normal. She wore a light blue top that appeared to be the same tight, stretchy material as the white one she wore Sunday. She wore no bra tonight and her nipples were standing proud. She had on a matching skirt that hugged every inch of her round succulent ass. It only went about half way down her thighs, highlighting her beautiful legs. She wasn't wearing stockings, her gorgeous bare skin glowing as I appraised her. "What do you think, baby? Momma still got it?" She was grinning waiting for my response. "Mom, you've always had it and I think you always will. You look scrumptious as always." She came over quickly and hugged me close as I lowered to kiss her cheek. She held me in a bear hug, not wanting to let go. I hugged her back, placing a little more feeling in it this time. "I love you, mom." "I know honey. But when your son gets married, a mother always feels like they are losing him to another woman." "Ah, you'll never lose me ma. I'm a leech just like dad. I'll be in your life forever whether you want me or not." "Please don't compare yourself to him. You're much better than that. And promise me you'll always be better than that." "I promise mom. But don't be too hard on dad. That war was pretty tough on him and he needs help. Sooner or later he will realize that and get help. Or he will die alone, a bitter old man." "I vote for number two. They give a guy a Purple Heart for a bar fight and everybody thinks he's a hero." Mom was still bitter because he lied to her, never wanting her to know the animal that was unleashed when he was in the war. "I know he told you it was a bar fight, mom, but they don't give out Silver Stars for bar fights. I looked it up online. What he went through wasn't pretty and he did risk his life for his fellow soldiers. Cut him some slack and maybe he'll try to get help." I didn't like him much either, at least not the man that he had become. But he was my dad and an ex-soldier and he deserved some support. "Yeah, well he's gone to rehab three times at the VA and it's never lasted more than two weeks. Didn't know that did you? He's not the only one that knows how to lie. Back surgery, yup that was rehab. Out of town training, again was rehab. Colon surgery, well that was real but I had the VA send him back to rehab for another month while they had him. He's had his chances. I can't take any more." "I'm sorry mom. I didn't know." I hugged her to me again. There were no tears, she was beyond that stage. "Whatever you decide mom, I will always be here for you." We stayed clinched for several minutes. I could feel those nipples starting to burn into my skin as her hands began to run up and down my back. She turned her head and kissed my neck softly. My cock started to swell and I started having feelings again that a son is not supposed to have for his mother. Still I wondered if the feelings could be mutual. I pushed away lightly, "Hey, we're supposed to be having fun. Let's get this dress on and see if you can turn your son into a real woman," I joked. "I'll get the beer," she said. "The dress is on my bed." She smiled, the glow returning to her skin and just like that she was back to being mom. I went into the bedroom to find the dress laid out on the bed with a lacy, black bra next to it. A pair of shiny patent leather pumps was on the floor. I guess I was really going through with this. I actually started to tingle in anticipation, for some strange reason hoping that I was going to look stunning. My First Halloween Party I stripped off all my clothes, taking the time to fold them like I had been taught. My little monster was starting to rise again as I opened the nylons and pulled them on. It was a sensual feeling that I hadn't been expecting and my cock gave a little lurch as I ran my hands along my legs. Could I really go through with this in front of my mother? I forced the thoughts from my mind and grabbed the bra, noticing that it hooked in front. I wondered if mom bought that special for me to make it easier or if it was one of hers. I brought it to my nose and inhaled, her perfume fresh on the soft material, an affirmation of her ownership. I felt even naughtier as I slipped it on, knowing that she had worn it recently and not washed it for me. I stepped into the dress, a little more snug than it had been Sunday night when I first tried it on. I adjusted the front and then reached back and pulled up the zipper. I glanced in the mirror and noticed how well I filled it out. Having inherited my mother's round ass had always been a plus for me with the ladies, but now it looked even better than in tight jeans. "Everything alright in there?" mom quizzed, evidently worried that I couldn't dress myself. "Doing fine, mom. Be out in a minute." I grabbed the wig and situated it properly on my head while looking in the mirror. To me, my face still looked like a guy's and my chest needed a little help, but the rest of me didn't look to bad. I slipped on the pumps and they were almost a perfect fit. A little narrow but the length was right. I guess Aunt Alice did have boats for feet. I took a deep breath and opened the door, the anticipation once again building along with the throbbing piece of meat between my legs. The heels were only a half inch and I found them fairly easy to walk in as I strolled back to the kitchen. Mom was just finishing her first beer and set the bottle down slowly as her eyes traveled up from my feet to my face. "Wow. Well the body's almost right. We'll need to fill that bra with something and try the make-up to be sure. I'd still shave my legs if I were you." She was studying me, checking my legs and butt, then my top and wig. "Any idea what you want to fill your bra with?" she asked. "I've got oranges or you could try pair of your father's socks," she offered. "I was thinking water balloons. They should bounce around like silicone implants if I fill them right. I brought a bag of balloons with me just in case," I said. "If anyone gives me a hard time at the party, I can just whip them out and throw them at them." "That's a great idea," she laughed. "Why don't you fill them up and I'll get my make-up kit." I downed half my beer before going to the sink and filling the balloons, making sure both were about the same size and tied tightly. I lifted the top of the dress and placed each one inside the bra, adjusting them so the balloon opening was away from my skin and towards the material of the bra. I stepped back over to the table and the jiggle felt right as I sat down and polished off the rest of my brew. My manhood was stretched down the leg of my pantyhose now, and I could feel it dripping down my leg. I hoped it would stay in one place and not go down far enough for mom to notice. She came back with her kit and stopped, her eyes going straight to my chest. She started to get that hungry look that Amy had on Sunday night. "That is a definite improvement, honey. They fill it out and spread at the same time. Great idea." She grabbed two more beers and set the kit down on the table. She pulled her chair directly in front of mine and positioned her legs outside mine so she could get closer. She had to raise her skirt to do this and it was now open almost to her crotch. My cock gave a little lurch as I imagined what her snatch looked like and my blood pressure rose as I thought that I might actually see it if she kept moving around. What are you thinking you fool? She's your mom. Stare straight ahead and stay focused. My conscience admonished me every way possible until I lifted my eyes and looked straight ahead. Straight into those crystal blue eyes. I remembered looking into to those as a child and how warm and secure I felt. They still made me feel warm, but not in a childish way. She was spreading the make-up on my face, her hand passing in front of my eyes and breaking the trance I was in. She started to smooth it out with her fingers, her touch now electric in my heightened state. I looked at her inviting lips, most of the lipstick worn off from drinking, but there was still a very sexy shade of pink and I wanted desperately to lean forward and kiss her in a manner not befitting a mother and son. She brushed some powder on me next. "Close your eyes sweetie. Don't want to get anything in there and I'll be doing your eyes next anyway." My hard rod was pulsating now and I could feel the precum flowing down my leg. She moved in closer and I could smell her perfume again which didn't help my situation at all. I felt myself getting light-headed and reached out to steady myself, my right hand finding her left thigh. "You alright honey?" she asked, true concern in her voice. "You look a little flushed." "I'm fine mom. Just feels a little warm in here. Maybe if I sip my beer I'll cool down a little." She stopped for a moment, a slight chuckle escaping her lips, an indication that I didn't have her fooled one bit. I downed about half the bottle and took a deep breath. I did feel cooler and I think my normal color started to return. Mom went back to work as I closed my eyes again. I could feel what felt like pencils and brushes and she alternated the instruments of my demise. I placed my hand back on her thigh to steady myself but got no response from her this time. Her leg felt warm as she finished my eyes and started drawing an outline on my lips. Her left hand touched my face as she tilted my head back slightly to apply the lipstick. The smell of her perfume, the light touch of her hand, and now the sensuous feeling of the satin lipstick being smoothed on my lips was causing the pressure to build down below and I knew if we didn't break soon, I was going to blow like a geyser and probably be forever banned from this house. Mom stopped and took a hold of the hand I had on her thigh as she stood up. I stood up, opening my eyes and looking at those beautiful blue eyes again. They had a look of longing, no hunger, in them as she continued to appraise her work. She let go of my hand and stepped back. "Damn but you're beautiful. Ahem, sorry about the language sweetie. Let's get you into the bedroom and see if we can do something with that wig." While mom was clearly flustered, she was still more in control than I felt at that moment. I could feel my throbbing manhood pushing against the dress and knew it was tented out. Fortunately, mom was currently fixated on my face and didn't notice. As I followed her into the bedroom I couldn't help but notice an exaggerated wiggle of her mesmerizing hips. She had to be feeling similar thoughts as mine and that idea only stoked my fire more. I sat on the bed facing the mirror as she climbed onto the bed behind me, brush in hand, and started stroking the hair. She styled it so it spread a little more right to left and it seemed to balance better with my face. My face! I looked into the mirror not recognizing the slutty bitch that was staring back at me. There was enough eye make-up for me to be doing a photo spread for a trashy porn rag. My skin looked flawless and my lips glowed a deep red like Jessica Rabbit. Mom dropped the brush and placed her hands on both sides of my face, twisting it left, then right as she admired her handiwork. Her nostrils flared as she let her hands brush against my ears sending chills down my spine. She lowered her lips to my ear, kissing softly as I heard a throaty voice say, "You look good enough to eat." My cock lurched again and I wanted so badly to just turn around and take her, but she is my Mom! Her face was against mine as we looked at each other in the mirror and she wrapped her arms around me. I was a quivering tower of mush as I sat still staring at the two beautiful women in the mirror. My mind was telling me that I could fuck either one of them, the reality that I was one of them still not settling into my brain. Mom hugged me tight and kissed my cheek before lowering her arms and grabbing both of my faux tits in her hands and shaking them wildly, laughing in that mom way that I had become so accustomed to over the years. I had to laugh with her, falling back on the bed and pulling her down with me. Our faces just inches apart, I pulled her closer and kissed her right on the lips, still laughing. She stopped laughing and her eyes told me everything I needed to know. She leaned forward, taking the lead as she kissed me deeply, a kiss of lovers, of incestuous lovers. I was burning up trying to control the pressure building in the pantyhose as I my cock strained and slid along my soaking leg. I slipped my tongue between her hungry lips and she sucked on it hard, and then slid her tongue softly against it, a duel in the dark. My cock was aching as the cum exploded against the tight nylon hose, soaking out through and I was sure spotting the dress. I grabbed my mother's round bottom and pulled her hard against the towering geyser between us, the pressure causing a second flood of juices to spurt forth as stars covered my complete field of vision. I held her tight, my schoolboy crush finally realized, with an endless stream of cum exiting a cock that refused to die. She pushed back but softened the kiss, realizing what just happened and for once in her life, not sure how she should respond. We continued to kiss softly for several minutes as my body returned to normal, the eight inch monster retreating back into the pantyhose to hide. "I love you mom. I know you think that's wrong, but it's just the way I feel. You are a beautiful, vibrant woman who deserves the best things in life." "Honey, I have the best thing in life. God gave me you and I have been forever grateful. But you and I both know this is wrong and right now we both have spouses, regardless of how we may feel about them. "She grabbed some tissue off the nearby nightstand and lifted my dress, trying to sop up the mass of white goo that seemed to be everywhere. She grabbed more tissues and pulled my cock from the hose, the first time she had touched it since I was small child. It grew instantly at her touch and she squeezed more cum from the head and wiped it clean. She tucked it back inside and looked at me, a stern motherly look on her face. "You had better strip the clothes off and hop in the shower. Der Furher will probably be wondering where you are. And it's a work day for both of us tomorrow." I wanted to return the favor to her but I knew she was still conflicted about her feelings so I thought this might give her a chance to mull over our options. I unzipped the dress, pushing it over my hips and allowing it to fall to the floor. My long cock was perfectly outlined against translucent material of the nylons. Mom watched like a starving POW eyeing a perfectly cooked steak as I lowered the nylons. I knew there wasn't much hope of salvaging them so I wasn't too gentle as I pulled them off, fully exposing my manhood to my mother. She stared longingly but made no move to assist me. I removed the wig and tossed it on the bed. Mom unsnapped the bra for me and she kissed me on the neck and shoulders before pushing me away and getting up to gather my clothes. I used her make-up pads to get most of the stuff off my face, then hopped in the hot shower and used a wash cloth to get the rest. I scrubbed every inch of my body almost torturing myself as I did it. Once done, I toweled off and wrapped it around my waist to head back to the bedroom where my normal clothes waited. Mom had taken my costume and I heard the washer start in the basement as I dressed back up into my suit, not bothering with the tie in my pocket. When she came back upstairs, I gave her another deep kiss, but she stopped it and stepped back. "A lot has happened tonight darling. Why don't we both just think on it for a few days and we can talk about it in more depth once your party is over." I knew she was right, nodded in agreement and headed out the door. When I got home, Amy was waiting. "Well how did it look?" "I was the sluttiest whore this side of Vegas." I said it like I knew there could be no other outcome. "It was a lot of work and I'm exhausted so I'm going to bed now." I kissed her cheek and left the room before she could say anything. She may have suspected something was wrong, but she didn't bother to respond. I slept like a baby that suffers from night terrors. I kept picturing my mom and I having sex and then having a deformed baby nine months later. The alarm clock couldn't ring too early for me. ************************************************ I got a call from mom on Friday to tell me dad was back in rehab. He'd had a nervous breakdown and they wanted to keep him for at least two months. She informed them that it should be long enough for them to find a new place for him to live. She was filing for divorce. She also suggested that Amy and I should be at her house at least two hours before the party Saturday to get ready. I agreed and avoided Amy as much as possible after dinner. Mom's talk of divorce got me thinking about my own marriage as well as that of my friends. Jack, Billy and I had all grown up in the same neighborhood and had been friends a long time. Billy was the first to marry, not because he wanted to but because Mary told him they were getting married. Mary was a petite girl with short brown hair and a pretty face and no one that knew her would have suspected that she was a worse shrew than Amy. She had been starring in plays in school and local theatre companies since she was a child and was used to getting her own way. Billy was just easy going and her personality didn't seem to bother him that much. He always had a joke for her nasty comments and loved going to her plays and hanging around afterwards with the female cast members. He never said if he was getting any action from it, but it would explain why he didn't care that he rarely had sex with Mary. Jack thought he was a comedian. He had more one-liners than Henny Youngman. He was a little shorter than me but also a little more muscular and liked to be the leader of the group. For some reason, he enjoyed picking on his wife Diane much like Amy did with me. I think he was having a hard time adjusting to the fact that he married some one more attractive than he was. Diane was a gorgeous blonde about two inches taller than Jack which made her almost my height. Her breasts and hips were perfectly proportioned to the rest of her frame and she looked great in a bikini. Her shoulder length blonde hair framed her angelic face which rarely had any make-up except for a light coating of lipstick. She had a sweet personality and everyone loved her. She was the girl that every guy wished they had married. She tolerated Jack's jokes and put-downs in public, but when they were alone she would put him in his place. We had taken one group vacation once and Diane and I always seemed to be paired together in pleasant conversation while the other four were arguing and slamming each other with insults. Amy and Mary were always at odds with Jack about what the group should be doing next. Billy usually played peacemaker. Saturday came around and I awoke early and went into the bathroom. I decided to shave my legs and get that out of the way, placing a towel on the floor and using my old electric razor as I watched the pile of hair that ended up on the towel. I felt my legs expecting nice smooth skin but it was all stubbly and I knew I had to use my regular razor. The sharp blade could now glide easily over the stubble just like shaving my face. The skin was baby-butt smooth after and I felt my erection grow as my fingers tickled the sensitive nerves. I kept trimming hair, doing my balls and most of the area around my engorged prick. I wanted to jerk off badly, but resisted and finished cleaning up and got dressed. Amy was just waking up as I finished my breakfast and headed outside to start my fall raking. I found myself anxious and somewhat exhilarated by what was going to be happening that night. My daydreams carried me past lunch as I kept raking leaves all day not realizing what time it was until Amy called to me. I quickly ran into the bathroom for a shit, shower, and shave. I used Amy's deodorant, the sweet smell getting a rise out of me once again. I pushed that idea from my brain and pulled on the clean clothes I had brought in with me. I walked out of the bathroom to find Amy already dressed in my baseball uniform, her hair pinned and tucked neatly under the cap. But even her small breasts stood out against the stretchy uniform material and I told her so. I got an old ace bandage I had and had her raise the uniform up so I could wrap it around her. In my heightened sexual state, even her small breasts and hardened nipples got a rise out of me and I fondled one before she loudly protested. I wrapped the ace bandage around her, probably a little tighter than it needed to be, and hooked it. She lowered the top and tucked it back in now looking very much like a scrawny ball player. The scowl on her face and lack of any make-up gave her a gruff appearance. We grabbed the food and drinks we were taking to the party and headed over to mom's house to get me ready. Mom met us at the door wearing tight pink shorts and a white tank top with no bra. Her large firm breasts stood out proud and stretched the material to its limits. Even Amy was looking at her differently. "Hey babe, wanna go to party tonight?" Amy drawled, trying her hardest to sound like a guy. She slipped an arm around mom's waist and pulled her close like she was going to kiss her. But mom pushed her back. "Sorry Dude, but my heart belongs to another," mom countered as she came over to hug me. Her nipples sent chills through me as she ground them into my chest like a stripper would during a lap dance. I separated from her and then stood behind her and wrapped my arms around her waist. My turn to grind as the hard-on she created was now between the lovely cheeks of her ass. "Yeah, sorry Dude," I said to Amy. "She's my girl." Mom was blushing as I kissed her cheek and turned and jogged to the bedroom. The clothes were laid out just like Tuesday night. I shut the door and quickly stripped, the anticipation rapidly building inside me. My cock was standing out straight and I gave him a few quick rubs thinking about burying him between mom's cheeks again. I pushed those thoughts from my mind again and picked up the lacy, black bra, getting it in place and hooking the front clasp. I stepped into the dress and zipped it up like I had been doing this for years. I sat on the bed and rolled the stockings, then pulled them over my smooth skin, shivers coursing through my body from the sensuous feeling. As I pulled them over my once again growing beast, I decided to push him up against my belly instead of having him grow down my leg and risk tenting the dress. I gently picked up the wig and placed it on my head, my fingers giving it a few pulls here and there to get it to look like the styling mom had done before. I slipped on the patent leather pumps and headed out to the kitchen to finish my look. Mom had the water balloons already and came over to place them in my bra. Her fingers roamed more than was necessary as she got them properly positioned, a hungry grin on her face as she looked up at me. 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. My First Halloween Party "Have you done this before?" I asked. "No, but it sure was turn-on," she replied. "I'm dripping now." "Look, maybe we can get together later this week. I'm not promising anything. We both need to think about this and how it could affect our futures." "Sure, I understand," she said rolling the pantyhose back up and leaving my once again stiffening rod pointed towards the heavens. She wiped a little of the lipstick smears from my mouth and gave me a quick peck, then led me out to the door. We hugged at the door and I went out to the car. Missy opened her door and slid over next to Billy making room for me in the front seat. The cool fall air was rushing up under my short dress and I wondered how girls ever wore dresses in the winter time. With the nylons providing almost no friction, the dress slid way up when I sat down leaving my sexy legs and apparently my crotch exposed. Billy didn't say anything, just backed out of the driveway and headed towards my mom's. "You know, Missy is really hot for a threesome tonight if you're up for it." Missy slid a hand over my crotch and I was quickly back to a full bone and enjoying the feeling of her hand rubbing up and down. "Maybe another time," I replied. Missy started to remove her hand but I grabbed it and put it back on my hard-on. She had a hurt look on her face at the rejection. I turned her head towards me and kissed her, a deep warm kiss. She slid her tongue into my mouth and I felt my cock jerk a little. I just wanted her to know that I wasn't bowing out of her plans because she wasn't attractive enough. Billy was now furiously trying to open his pants while driving, so I had took Missy's hand and told her to help him instead. She had his pants open in a flash and was stroking his meat. She turned and leaned down to give him another blow job, presenting her cute tiny ass to me. It was easy to move her thong over and slide a finger inside her. She was dripping wet and I pulled my finger back out and started sliding it against her clit. I plopped my thumb inside her and began massaging her G-spot (or at least what I thought was her G-spot) while still fingering her clit. She stopped sucking Billy's dick as her breathing quickened and she started screaming, "Fuck, fuck, fuck!" I pulled my fingers out and she sat back up, still breathing hard. She turned, and then straddled me, kissing me passionately while her hands searched for my cock. Billy was having a hard time watching the road. "Hey, what about me?" he pleaded, his stiffened prick waving in the air. "We're almost at the house Billy. Just watch the road." I took her hands off my prick and moved them to my boobs, feeling a little like the slut they had dressed me up to be. She laughed as she played with the squishy balloons. Billy pulled into the driveway of my mom's house and Missy climbed off me. His rod was still sticking straight up but the purple head was now glistening with moisture. "Thanks for the ride. Maybe you two should take care of that problem before heading back into traffic," I suggested. They were humping away before I was in the house. Mom was waiting for me wearing her short, white satin robe and it looked like nothing else. She came over to me and gave me a big hug. As I wrapped my arms around her it confirmed that she had nothing on underneath. "Your make-up is messed up," she offered. "And isn't Billy coming in to say goodnight?" "Billy is a little busy right now. Want to watch?" I went over to the window and opened the curtain a little and mom peeked out. Missy was riding Billy hard and I heard mom gasp. The back of her robe exposed part of her naked butt as she was leaned forward to watch kids fucking. I moved in behind her, raising my dress and allowing my nylon encased cock to rub up against her naked crack. She moaned, pushing back against me while still watching them fuck outside. "You sure you really want to be doing this Joey?" "As sure as I have ever been in my life mom," I replied, pulling my hard cock out and sliding it from her clit to her asshole and back again. She spread her legs and I eased the angry purple head inside her. She was surprisingly wet and she pushed back again taking even more inside her. Between Diane and Missy and this slutty outfit I was wearing, I was pretty worked up and ready to blow. I started to get into a steady rhythm, pounding her hard. Mom sensed how close I was and pulled away and closed the curtain. She dropped her robe and lay down on the kitchen table. I put my cock back inside her and started slamming her again while I diddled her clit. She locked her legs behind me and squeezed me closer forcing shorter, faster strokes. The tingling started in the head of my cock and quickly spread to every nerve ending in my body as the cum rushed forth splashing against her cervix. I held my cock in place as I felt mom's cunt grip tightly as her own orgasm was exploding. Her eyes closed and her back raised up as her body stiffened. She started to relax her back and her legs were pulling me close again. Still hard, I started pumping her and reached down to diddle that large nub again. This quickly sent her over the edge as a second orgasm quickly washed over her body. A she started to come down again, she sat up and we kissed. It was a kiss of lovers and not a mother and son. The incestuous act may have increased our passion, but it also increased our love for each other. I pulled my cock out, cum dripping from it onto the floor. Mom reached down and ran her hand over it, taking some of the goo and raising it to her lips. She sucked her fingers into her mouth as I started to fondle those wondrous breasts that still defied gravity. They were soft yet firm and the turgid nipples had been hard since I first walked in the door. It was an act I had played out in my fantasies occasionally as I masturbated as a teen, but now that it was really happening, it was more exciting and sensual than I had ever dreamed. Her skin was softer than Amy's, her breasts significantly larger, and her face more beautiful. "Honey, as sexy as you are in that dress, I really think it's time you removed it and wiped off the make-up. Then we can do this again as a real man and woman." I pulled off the wig and unzipped the dress, letting it fall down my body, tickling my legs as it passed over the stockings. I reached up removing the balloons and tossed them into the kitchen sink while mom unhooked the bra. She sucked my flat breast into her mouth, nibbling on the tiny nipple as it became erect. I didn't have time to remove the make-up; I had to have her again. I picked her up and carried her to the bedroom, my cock thickening again and poking out the top of the stockings. I put her down on the bed and climber on top of her. The nylons rubbing between our flesh was making me quiver and the reason I didn't want to remove them. It was a new and exciting feeling and I was enjoying every thrilling minute of it. I sucked her lower lip between mine and ran my tongue softly along it. She then did the same with my upper lip before our tongues started sliding back and forth, a prelude of what was to come for our sexual organs. I moved lower to kiss her neck, her perfume filling my brain and causing some goo to ooze out my cock head and onto her flat tummy. I nibbled her ear and then sucked her earlobe, tonguing and biting softly. Her fingers started raking softly down my back, the shivers returning again and more clear liquid oozed out. I moved lower kissing her chest, eventually finding her ample breast flesh, kissing it softly until I found the long hard nipple protruding from the white mound of flesh. I sucked it hard and she grabbed my head running her fingers through my hair. Everywhere she touched me caused my body to quiver helplessly. I squeezed the other breast as I started to kiss my way down her body. Her tummy was flat and taut as I found the puddle of ooze I had left their earlier. I licked up the salty liquid, dipping my tongue into her cute navel. I could feel her body start to quiver now. I kissed lower, encountering the thin wiry pubic hair of her landing strip. It was a slightly darker shade of blonde than her head, but I figured her hair was colored when it was styled. She smelled musky, her excitement leaking out like mine had been doing. I lapped it up lovingly, running my tongue over her clit and down through her moist slit. She started to moan as I shifted position, moving my hips back towards her head. I could now move my tongue down her slit all the way to her clean brown hole. She moaned louder and pulled my leg to get me to straddle her head. I took the hint, positioning my cock directly over her mouth. She pulled it down to her waiting lips as I captured her clit between my satiny lips and began to suck lightly while my tongue danced across it. She was groaning now as she sucked my throbbing tool deep into her mouth. Her hands grabbed my ass and pulled down more shoving my cock down her throat, a brief vision of Tammi came into my brain as the chills ran through my body. I nibbled her clit softly, and then did a machine gun flicker of her clit with my tongue. The rapid motions had her hips rising as she convulsed in another climax. She had to let my cock escape to get oxygen back into her body. Her breathing ragged, I sat up and turned around, positioning myself between her spread open legs. I diddled her clit with my purple monster and she came again in a matter of minutes. She grabbed my ass and pulled me forward, my pulsating tumescence sliding easily into her moist tunnel. We had a rhythm going in seconds and I precipitously close to another explosion as I pummeled her lovely body. We kissed deeply, her perfume finding its way to my flared nostrils and pushing me over the edge, boiling hot liquid shooting deep into her and splashing against her cervix. I continued to pump into her even after the flow of cum had stopped and she came once again, grabbing me tight as her body convulsed. Our breathing was a deep gasp as we searched for air. I kissed her softly, then franticly afraid that this could end our relationship. I need not have worried. Mom was calm as she slowed our kissing and looked me in the eye. "It's alright Joey. Everything we did is alright. We are two adults, deeply in love and overcome by lust. I realize you will be attracted to other women, but as long as you are attracted to me, we can continue to do this." "I'm going to ask Amy for a divorce mom. I just can't take her attitude anymore. Would you mind if I moved back home?" "Mind? I would expect it. This is the generation of the boomerang babies, isn't it?" She was smiling knowing she was getting her little boy back, only he was a man now, more of a man than his father had been. "When are you going to tell Amy?" she asked. "I'll wait until tomorrow. She's having sex with Mary right now and I wouldn't want to interrupt them." "Really? How do you know?" "I could tell by her voice on the phone when I called her earlier. I interrupted them." "Might help your divorce if you had pictures. If you went home now you could catch them in the act." "Or she could come back and try to get evidence against us. It's not worth the risk. She can have the house and the mortgage. I just want you." "I love you Joey." "I love you to mom. I guess they were all wrong then. You can go home again."