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.

Report Story

byMalomar© 10 comments/ 204991 views/ 114 favorites

Share the love

Report a Bug

5 Pages:1234

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: