October Surprises

Published on Jan 16, 2020

Transgender

October Surprises 1

DISCLAIMER: This is a fantasy depicting heterosexual and homosexual acts involving men, women and boys. The story is intended for adult readers and not minors. IF YOU ARE NOT OF LEGAL AGE TO BE READING THIS STORY OR IF YOU FIND SUCH MATERIAL OFFENSIVE, PLEASE LEAVE. All characters are fictional and in no way related to any person or persons living or deceased.

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Since I was about 12 I have found a lot of pleasure in wearing womens'

underwear. Bras, panties, slips and nighties are my favorites but once in awhile stockings too. Over the years I have acquired a lot of panties. all nylon, and since I turned 45 I have been wearing them most of the time under my normal clothes. I didn't think that my wife knew this although early in our marriage I told her how much I liked nylon and silky things. I have fantasized about sex as a women by sucking a dildo and sometimes shoving it firmly up my ass. I wear bras around the house when I am alone and have wished for a long time that my wife would find out and maybe be interested in playing along with me. She is straight-laced in bed to say the least but she does let me fuck her in the ass. Wish I could do that with both of us "dressed" sexy. This is about wishes coming true. This past October my wife came back from her card club and told me that the other ladies had planned a Halloween Party and the kicker was that each costume had to represent the opposite gender of the person wearing it. Women dressed in mens' costumes and men in womens'. The idea was a bit kinky for this straight group but I found it interesting and wondered what I could get away with. I figured that most of the guys would just throw on a dress over their clothes or just come "Butch" like a lesbian theme. I was getting a hard on thinking that the opportunity to go out in public with my hot stuff underneath had arrived. The problem was where was my wife on all of this.

"Sounds good dear but what will I be wearing?"

" I will take care of everything but you will have to shave you legs and remove your chest hair in case the dress is low cut."

I had no idea of what was going to happen with this but I was turned on by the idea that she would make me look all femme and be there with me to experience me as a girl. I questioned myself about volunteering my personal stash of lingerie for the production but held back on the idea to see where Donna went with it. My thoughts were on this all day on the job as every time I moved and my cock moved around in the green nylon panties I had on today I had to stay seated at my desk to avoid displaying my bulging trousers to the office staff. When I arrived home from work Donna called me up to the bedroom. She was in the bathroom playing with her hair or something but on the bed was a pair of medium blue lace, boyshort type of panties. Wow they looked hot and i guessed she was going to give me a little show by slipping them on while I watched.

"Put those on and see how they fit." She yelled out over the noise of the blow dryer. "See if they fit you for your costume."

I was so excited by the idea that I popped by belt loose and had my trousers on the floor in a few seconds. I yanked my underwear off, forgetting they were green nylon high cuts, stepped into the lacey ones and slid them over my legs over my nuts over my hardening cock and let them settle into place across the cheeks of my now hairless ass. Looking down I saw my tool swelling and bulging the lace material from my balls to my hip. The fabric was a bit scratchy but I was sure a gentle wash and dry would soften them up.

Donna killed the dryer and stepped into the bedroom to check me out. "Looks like you like them" she said eyeing my firm member pushing the lace outwards.

"Yes they fit OK honey. A little scratchy but...

"You will get used to it" she said. "Cute ones on the floor too."

Oh crap I left my panties on the floor with my pants. I was dead meat I thought.

"You will have to model the whole collection you have sometime now that you are doing Halloween in the female role."

"Walk around for me and model those" Donna instructed.

I did and the sensation was very hot as they kind of tickled my ass and my balls as I moved.

"Rinse them in the sink and hang them to dry in the bath so you can wear them tomorrow.

"What is tomorrow?"

" Just your first day to get into the "female" thing. Wear those to work and around the house to break them in."

I was game for that and her next suggestion as well.

"Since you only wear briefs to bed how about wearing the hot ones in your drawer. More lady like. Gets you conditioned."

Get my hard and blown I hope too.

Donna made me wear the new lacy ones to work the next day and it was tough. All of the ball tickeling and butt rubbing of the boyshorts and it was hard to keep from beating off under the desk. All I could think of was what might be waiting for me when I got home that night. Once again I found costume materials lying on the bed and my wife in the tub soaking.

"Try those on." she said "and I will be done soon."

I looked and spotted a bra to match the panties I already had on. A careful exam revealed that Donna had added some extra satin material like the sides of the bra to the back so it would fit me better. How did she know my size? Oh yea, she knows about my stash.

I pulled it around me. Lacy cups with satin sides, again the same blue but with a small ivory or beige colored bow right between the tits. Low cut, almost a demi style but with air pads in the bottom of the cups to add extra push for cleavage. I clipped the three hooks together and twirled it around to the front before I wiggled it into position. If there had been a mirror in front of me I would have come by now, even before I slipped my arms into the straps. Had to adjust them a bit but once properly enclosed by the bra it was heavenly. The tightness was exciting like a hug and as I rubbed my hands all over my tits the texture of the lace had me ready to blow in my boyshorts. I have enough "man boobs", exaggerated over the year by wearing bras when I could, that with the design of the bra and the push up pads I was showing off a reasonable solid "B" cup titty and my nipples were like little stones rubbing the lace inside. No chest hair now was a real bonus. Would I ever stop playing with my tits long enough to put on the stockings still waiting on the bed?

Settling down a bit I sat on the bed and bunched up the first stocking to put it on. They were white with a very silky feeling and had a swirling pattern in them. In went my foot settling my toes firmly to the front. While seated I got them over my calf then stood and brought them as far up as they would go. They had wide lace elastic at the top to hold them up without garters and the tops came right up to my crotch. Dam I wished I had a mirror in the room. Got the second one on and when I walked they scratched my crotch so nicely. I had to go look and headed for the full length mirror in the bathroom. Just as I opened the door Donna appeared in a short robe and her eyes about popped out when she saw me.

"Oh my gawd, you look so hot! And Hard too! I bet you could use a good blowjob right now."

She opened her robe to reveal her hot new undies then dropped to her knees and placed her hands on my hips. She caressed the fabric and told me how nice it felt. Then she traced my hardon with he fingertips thru the lace in front. Soon her face was in contact moving back and forth over the covered surface of my bursting tool. One quick pull and I was free with my cock bouncing in mid air. Her hands back to may hips with the panties just below my nuts she flopped my cock back and forth over her face. This was a new wife, where did she come from.

"Make me!" she said looking up staring at my new bra and tits from below. "Make me suck your cock!"

"Open wide, Bitch. You want cock you are going to get it. In your mouth, down your throat and all over your face."

I had never talked dirty to her in all of our married years. She loved it and tried to resist. With one hand on her head I put my finger in her mouth and swirled it around. I added a second one and pushed my hand into her mouth feeling her tongue attack my fingers.

"Here it comes" as I pressed my prick into her now open mouth. I let it slid over her bottom lip. "Tongue it baby, taste the juice!"

She lapped at the tip to sample the pre come that had appeared. I lasted about a minute. Looking down and seeing my tits in a sexy bra, my cock sliding in and out my wife's wet mouth and her in satin bra and panties I blasted about 5 shots of the thickest come ever into her. Shot one when I was deep into her face. Then I pulled back to let 2 and 3 cover her tongue. The I pushed her away just a bit so my cock head was just touching her lips for # 4. It covered them and dripped off. She held my cock, opened really wide and I watched the last load land on the end of her tongue. Oh shit was that amazing. Then Donna jumped up and shoved her tongue into my mouth, come and all. I resisted for a second but she held me so tight and was going insane with her snake like tongue in my mouth. I thought I was giving a blowjob. Actually that comes later. I had never felt like this. We went right to bed dressed as we were and I spend the next hour with my face buried in her cunt giving her the best head any girl could want. Girl on girl- I loved it.

She came really hard and I came again as well just from feeling my cock in lace as I humped the mattress while eating her and fantasizing about eating a dick instead. Careful what you wish for. I went to work the next day with many hot thoughts. I refrained from wearing any of my womanly underthings so that I could concentrate on getting some actual work done. Finally on my drive home I allowed my mind to wander about what was next in the new and interesting sex life we had discovered. Donna had gotten home first and I could sense the fresh clean smell in the air from her having taken a shower. Upstairs I found her already in bed with the covers pulled up around her neck.

"Take a shower, put on what I left for you and get back in here quick" came the instruction.

In the bath I saw a bright yellow satin baby doll nightie with pink lacing up the front and the back. There were bottoms to match. Glad I was in the process of getting undressed since my cock was about to rip thru anyway. A quick shower including shaving my balls nice and smooth, a little bath powder and into the satin sheath I jumped. I could hardly get my dick in the panties but enjoyed pawing and pushing my tool around in them to try and get comfortable. I love caressing my cock in such silky materials. Enough! Off to see the wife.

As I stepped into the bedroom Donna told me that I looked hot and told me she had another surprise. She pulled back the covers and she was naked. Her nipples were hard as rocks and her pussy looked wet already.

"I got us a friend you might enjoy. I know I will" she said while reaching under the pillow. Out came a big rubber cock about 18" long and thicker than me. 2 headed and very lifelike looking. Oh crap is she going to take all of that! Also wondered why it needed 2 heads. I sure was interested.

"Open me up and fuck me with this big rubber cock!" almost screaming. "Fuck me long and hard!"

Who was I to object. I knelt between her luscious creamy thighs and held the "friend". I was so heavy but it felt very comfortable in my grip.

As I started towards her wet pussy she said "Wait, you have to get it wet. Use your mouth on it. Make like its a real dick you are going to suck, pretty girl". "You know you want to".

I stared at the big pink head and brought it closer to my lips. Extending my tongue I acted sexy, swirling the tip around the crown and then licking back and forth over the tip.

"Suck the dick you cocksucker!" my wife shouted. "Shove it in your face and get it really wet and sloppy."

In went the head, the tongue still going at it. Saliva was running out of my mouth I was so excited. I probably had 5 inched in my face before I pulled it out POP and literally slammed it into her cunt. 7 or 8 inches into her horny twat all at once. I started pumping it in and out more excited by the sloppy sounds it made and the feeling of it in my hand and watching my naked wifes tits bounce around. As I moved I could feel the cool yellow satin slip back and forth over my hard nipples and my cock stirring around in the bottoms. I knew that I was making a mess in there. I was nuts with lust at this point. Pumping it in, caressing the shaft, feeling the fabric. I needed my cock worked on so I turned around in a 69 position. Without letting go of "our friend" I pulled my dick and balls out the side of the panties and lowered my crotch onto her face. My balls on her lips she extended her tongue and gave them a good bath. Still sliding the dildo in and out. Letting go of my nuts Donna told me to pretend she was a guy and suck her cock, meaning the other end of the pistoning plastic penis in her pussy. I leaned forward and bent the tool upward. This made it really tight in her twat and she moaned.

"Suck it now!" she said thru her moaning and I lowered my mouth over the part in my hand. As I did she slipped my cock into her wet mouth and I just started to imitate her motions and technique. My ministrations to one end created all kinds of good effects on the other end. Donna was soon having the orgasm of a lifetime and so was I. She was soaked in sweat, my face sloppy with pussy juice and her face had come from nose to chin.

"You like?" was her question as we untangled and hugged each other.

"I love this outfit, your tis, your pussy and your mouth".

"What you don't like my cock? You seemed to be very into sucking on it" she responded.

"Well I will admit it felt pretty interesting in my mouth and it sure got you going" I told her.

"In your girly mode dear you should like dick. It is only natural. Maybe some day you will get a real one." "Now since you mentioned my tits and you have not touched them, be a good little girl and suck my hard titties for awhile."

Her naked and me in satin we cuddled and I sucked her boobs until she had another come. Slept great.

More to come. You like? You dress up? You like to suck too?

lacylips@gmail.com

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Next: Chapter 2


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