A New Beginning

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Wife joins in for my first time.
3.5k words
4.55
205.9k
83

Part 1 of the 2 part series

Updated 10/29/2022
Created 03/29/2009
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"This story is about transsexuals. If you are not interested in this kind of story or find it offending, hit your back button and find something else. It plainly tells you what kind of story this is and if you don't like it, don't read it! There's no point in wasting your time just to read it and tell me how it offends you. I really don't care because you shouldn't be reading it in the first place if it's not what you like.

For those of you that are interested in these kinds of stories, I hope you enjoy it. There may be more added to it."

It's not easy to accept the fact that I ruined my own marriage. A lot of guys ruin their marriage by cheating on their wives with some piece of ass that wasn't worth it in the first place. Not me, I ruined it by becoming one of those pieces of ass.

From my earliest memories I knew I was supposed to have been born female. Being young, I didn't try to hide it because I thought it was how everyone felt and that nothing was unusual about it. Needless to say it freaked my parents out and I was discouraged from having those thoughts. They might have discouraged the actions, but the thoughts only got more intense as I grew.

My desire to become female never got in the way of my feeling for beautiful women, I think it made me more selective. I finally met the girl of my dreams and we got married. Sherry is everything I want to be. Long curly hair, soft delicate skin and every curve in just the right place.

I kept my desire a secret from Sherry. Mainly because I didn't feel like my desires would ever be fulfilled, so why risk it. I remember the day something inside me came to life. My desires grew to such an extant, that I didn't think I could make it another day as a male. I broke down and told Sherry everything.

She tried her best to be supportive and understand me. We started going shopping together and she helped me with hair and makeup. She even tolerated my lingerie during sex. I could tell she was uncomfortable with the new me but I was living my dream and continued anyway.

After a few months she told me she couldn't cope with it anymore. She told me it wasn't the life she wanted and she moved out. I was heartbroken and knew there was no way I could go back to pretending this part of me didn't exist so I let her go.

Sherry and I remained best friends and occasionally had sex, but I had a new secret that I was still hiding from her. I had started taking hormones and exercising to get my body in a more feminine shape. My face looked more delicate and my body weight was shifting to my butt and breasts. Sherry made a few comments about my breasts but I blamed it on my weight loss.

After sixteen months of hormones my body was filling out very nicely. I noticed people staring at my chest a lot and my entire attitude had changed. I bounced when I walked and noticed myself moving more womanly. I was preparing to tell Sherry and start living my life out in the open when she called and told me she needed a place to stay for a while.

She made it clear to me that we were roommates and friends and told me that even though we were still legally married that she wanted her own life and the ability to date. The thought of her with another man hurt me inside but I knew there was nothing I could do about it.

She started staying out later than usual and when she came home she had that fresh fucked looked to her. I was jealous but also finding myself very turned on. The image of her taking a big cock inside her tight pussy kept me awake many nights.

Friday she called me from work and told me that there was a possibility she wouldn't be home tonight. I knew what that meant and it made me wish I could trade places with her for one night. So I decided to take the opportunity of the house to myself and have some fun myself.

I got dressed up in a little black dress that showed off my new curves and did my hair and makeup. By now I was a pro at it and had myself looking sexy in no time. I was standing in our bedroom in front of the full length mirror when I saw the reflection of our sex toy box in the mirror. A wicked smile crossed my dark red lips as I made my way over to it.

I opened it and got out Sherry's realistic dildo with full heavy balls and sat on the bed. I slowly ran my painted nails along the life like skin wondering if Sherry was doing the same thing at that moment. I began licking and sucking at the toy, pretending I was her. I was getting so turned on, I began moaning and whimpering as I laid back on the bed with the toy still tightly grasped between my lips.

I pulled my dress up and my fingers began running across my little cock through my panties. I was working myself into a frenzy and knew I had to have it inside of me. I reached into the nightstand and got the lube out. My eyes closed and a sexy sound escaped my full mouth as my slick fingertip slipped into my panties and found my little hole.

I had two fingers feverishly working my hole and my mouth steadily working on the dildo when I heard the front door slam. I jumped off of the bed and tossed the dildo into the closed. I pulled my panties up and smoothed my dress down just as Sherry appeared in the doorway.

I knew I looked like I had been caught doing something and felt my cheeks redden even more when a very tall gentleman appeared next to her and put his arm around her waist.

"Did we interrupt something?" Sherry said smiling as she looked me up and down.

"No, I was just cleaning a little." I replied trying to keep my eyes down.

"Brad, this is my husband, the one with the little cock I was telling you about." Sherry said giggling.

I looked up and noticed they were both staggering drunk. His eyes looked me up and down then a smile crept up on his lips.

"I'll be damned," he said taking his arm away from Sherry's waist and walking over to me. "I would have never guessed it!" He said circling me and checking me out.

I felt so small and insignificant with him towering over me.

"I would have guessed you two were sisters." He said brushing my long curly hair from my face. His eyes became fixated on mine for a moment making me feel awkward but yet turned on.

"I'm sorry baby," Sherry said patting me on the ass, "We had a little too much to drink and your house was the closest." Her eyes got a funny look in them and she covered her mouth and ran to the bathroom and shut the door.

Brad staggered and leaned against the wall as I excused myself to go check on her. I held her hair back for her and helped her to her feet. She drunkenly brushed her teeth and said she had to go lie down. I helped her to the bedroom and didn't see Brad anywhere. I tucked her into bed then walked through the house to find him.

He was trying to unlock the front door, failing miserably when I found him. He said he was sorry for the inconvenience and it would probably be best if he left. I had the thought of letting him leave but was afraid he'd end up killing someone as drunk as he was. I told him it was alright and led him to the den where we have a fold out sofa.

He plopped down in the chair as I pulled out the bed and put a sheet and blanket on it. I turned to Brad only to find him passed out cold. I flipped the light off next to him and helped him to his feet and over to the sofa bed. He lost his balance and fell forward pushing me onto the bed with him landing on top of me between my legs.

"I'm sorry Sherry, I'm just so damn drunk baby." He said into the side of my neck giving me goose bumps. Just hearing him call me Sherry out loud turned me on a little.

I brought my hand up to his shoulder to roll him off of me when he grabbed it and held it flat against the bed. I gasped but before I could do anything his mouth had found the side of my neck. He nibbled and sucked on my neck causing me to melt inside. I found myself getting really hot and my hands wrapped around him as his groin began pushing against me.

My nails dug into him as he nibbled on my neck. I knew it was going too far so I pulled his head up to tell him to stop. As I opened my mouth to speak, his lips found mine in the darkness. I jumped back, the thought of another man kissing me scared me a little but when his hand began squeezing my breasts and pinching my nipple I gave in even more as his hot tongue explored my mouth.

I could feel his cock pressing into me through his pants. It was as hard as steel and my hips rotated up feeling him push against me. I couldn't believe how hot I was but my small flaccid cock hadn't even hardened. I was grateful he was so drunk or he probably would have felt that something wasn't quite right.

His arm went under me and rolled me over until I was lying on top of him. I put my thigh against his bulge and massaged him as we kissed. He pulled me dress up and over my head and tossed it onto the floor. With one quick motion he unsnapped my bra and freed my soft breasts. I felt a wet spot form in my panties as his warm mouth found my nipple and sucked on it.

His hand fell down my back to my panties and he pressed against me with a finger. I suddenly realized my hole was still lubed from my fingers just as his hand slipped into my panties and he squeezed my ass cheek.

Fear came over me and I started to panic. I had let this go way too far and I was afraid I was going to be caught any minute now. I wanted to jump off the bed and leave the room but I was afraid he'd see me from the light if I opened the door. I had didn't have a choice, I had to think of a way to satisfy him quickly so I could get out of this.

I slid my way down his body and unbuttoned his pants. I slid them off of him and wrapped my small hand around his throbbing shaft. I instantly felt powerful as his cock throbbed in my hand. His flesh was hot as I slowly began stroking him. I moved my other hand down to his balls and ran my painted nails along them making him tense up.

"Damn Sherry! You make me so damn hard! Why don't you put those sexy lips to work for me baby!" He mumbled as I stroked him.

I felt the butterflies in my stomach fluttering madly as I leaned forward. I stuck my tongue out and closed my eyes as it touch the soft velvety tip. I could taste Sherry's pussy on him, so obviously they had fucked before they came over. Brad gasped and I placed my lips around his head and squeezed his heavy balls in my palm. I slowly licked up and down the shaft and then put his pole back between my lips. I could feel his sticky pre cum begin to coat my throat and mouth as I let him fuck my mouth.

I could hear his moans mix with my whimpers as he began pumping faster. He tensed and moaned, I squeezed his balls again as he began shooting globs of hot cum into my eager mouth. I milked him good and licked up all his cum. I felt dirty and ashamed as I laid there still licking his softening cock but I was still very happy and proud that I had done a good job.

I got off of the bed and quietly left the room. I shut the bathroom door behind me and stared at my own reflection. My makeup was smeared and my hair was a mess. I looked like a used whore and loved it. I stayed in there for a while and reapplied my make up. I quietly crept down the hall and could hear Brad snoring.

I slowly made my way back into the den with him. The moonlight was shinning through the windows just enough to cast a soft, cool glow on his skin. He was lying uncovered and still nude. I sat down on the bed and watched him closely as I reached out and ran my fingers over his peaceful cock.

In not time it started to harden and he was still snoring. A wicked little smile crossed my lips as I realized I was going to get to have some more fun. I slid between his legs again and this time I gave him a long, slow blowjob. I took all the time I could to savor the memory of it.

His cock responded nicely even though he was in a deep sleep. Before long I let my hand wander down to my ass while I sucked him. I moaned as I slipped a finger into my lubed little hole. Suddenly I found that heat boiling up inside me again and wanted something real and big inside of me.

I carefully got up on top and straddled him. I squeezed my breasts as I began rocking my panties along his thick slab of meat. I reached behind me and pulled my panties to the side. I couldn't believe that this was actually happening and guided his big cock between my ass cheeks.

I rocked back and forth letting his cock get slippery from the lube, each time teasing my hole with the thick mushroom head. I leaned forward and arched my back as I reached around to try and guide him into me. It wasn't easy because I was trying not to disturb him too much.

"Here, let me help you baby." A soft voice whispered as another hand grabbed mine and took the cock from it.

I spun my head around quickly to see Sherry and just as I was about to start apologizing she put a hand at the small of my back and pushed the huge tip into my tiny hole. I gasped loudly and clinched my eyes shut as the sharp pain tore into me. She pushed down on me harder and I felt my hole stretching open as his head invaded me. I let out a soft whimper when the head passed my opening and I felt my hole close down around his hot shaft.

"That's it baby, take deep breaths and try to relax." Sherry whispered.

Both of her hands were on my hips guiding me down further onto that massive pole. I could feel every inch of him as he slid in further and further until I was down flat against him. I could feel his meat pulsing inside of me as my muscles contracted against him. I sat up straight and felt Sherry's naked body press up against my back.

She brushed my hair away from my ear and softly started licking and sucking at my lobe. "I've thought about this but never dreamed it would happen." Her hot breath whispered into my ear. Her hands began lifting on my hips then pushing me back down making me fuck him. I could feel her hard nipples glide along my skin as I moved.

Her hands let go of my hips and slid up my body to my breasts. Her mouth closed down on my neck and began to suck as her fingertips began pinching my hard nipples. I moaned softly and found myself gliding up and down on his cock with ease now.

"You know baby," She whispered as she played with my breasts. "You talk in your sleep sometimes." One hand slid down to my panties and pressed against my little penis through the fabric. "I know you've been taking hormones to get this sexy body."

I cried out a little at hearing that and felt a warm tingly feeling grow inside of me. I started bouncing faster, suddenly not caring if Brad woke up or not.

"Oh my, does the little whore like the feeling of a big thick cock?" She said teasingly as her fingers worked over my flaccid penis faster like she was flicking over a clit.

I leaned my head back against her shoulder giving her more access to my neck as I whispered yes.

"Good, I knew you would," She said between kissing my neck. "Now you know why I had to find someone else. There's nothing like a big hulking piece of meat ripping you open. It's so much more fulfilling than your little clit."

Her fingers were furiously working my limp penis making me bite my bottom lip as I rode the cock in my ass.

"That's it baby, come for me! Make your little clit squirt for me!" She said still biting my neck.

I tensed and felt that warmth inside of me boil up until it felt like a volcano going off inside of my stomach. Her hand covered my mouth as I cried out and shot hot juice all inside my panties. Sherry's warm hand quickly reached in a gathered up all my sticky cum and brought it up to my mouth. I greedily sucked her hand clean as she giggled.

I started to relax and catch my breath. My hips were slowly moving allowing his cock to glide in and out of me.

"No baby, you can't stop now." She said motioning my hips faster with her grip. "Welcome to womanhood, now you have to make sure he gets off whether you do or not."

Hearing her welcome me to womanhood was all it took for me to start bouncing my ass up and down.

"Yeah baby that's it, faster now!" Sherry said urging me on while her hand played with his balls.

I was panting and moaning as I rode him. I felt that pressure build inside me again and couldn't believe I was going to have another orgasm. I leaned back and nibbled on her ear, "I'm gonna cum again!" I panted.

Sherry giggled and started playing with my little penis again. My moans got louder and shorter and I started to feel dizzy. With one final push I pushed down and came violently as I felt his pole jump and spurt inside of me. I gasped as the hot creamy liquid filled me up and started leaking out between us.

Sherry turned my face towards hers and kissed me deeply as she gently nestled my limp penis back into my panties. I was breathing heavily as she lifted up on my ass and his thick cock plopped out of me leaving me feeling empty.

I leaned back against her with his cock nestled between my cheeks as she kissed me and held my trembling body. Her hands were still squeezing my breasts and pinching my nipples making me spasm as she giggled.

"Come to bed with me, it's time my girl learns to eat pussy the right way." She whispered helping me up off of the bed.

She walked me down the hallway with her arm around my waist just as Brad had his arm around her earlier making my fantasy of being her feel complete. When we got to our bed she pushed me down and began sucking on my nipples. I was in loving our new love, her mouth was so soft and warm.

She then rolled me over on top of her and pushed me down to her steaming hot pussy. I dove in and sucked and licked her clit until she was grinding hard against my face. She came loud and hard with her fingers tangled in my hair. She brought me up to her and kissed me deeply tasting herself.

I snuggled up against her and laid my head on her heaving breast. The entire night was playing over in my head as I started to drift off with her arm around me.

"Tomorrow's going to be a busy day for me and my new girlfriend. We've got so much to do!" She said kissing my forehead and holding me tighter.

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19 Comments
1Martiniman1Martiniman26 days ago

Wasn’t sure at first about this story as I wouldn’t have an ex-wife move in with me after divorce and watch her fuck other men, but then I kept reading and was rewarded with a very good story. It’s unconventional for sure, but if husband and wife or now wife and wife are happy…all is good. It turned out pretty hot and erotic…a must read. Hoping part 2 is just as hot.

ddedderrddedderralmost 3 years ago

Hot!! I dream of this happening to me

Riki1942Riki1942over 5 years ago
Wonderful Feeling

I'm not on hormones but I cross dress. I take loads up my butt bareback from a couple of "Special" friends and I can totally relate to that frenzied lust that almost makes you crazy when your ass is stretched around a guys hard cock and you know his cum is going to be inside you! You loose all inhibitions, you don't care who knows, hears or sees, your whole world narrows to the wonderful feeling of that cock thrusting inside you and the desperate need to know his cum is deep inside you!

NellaBarely2NellaBarely2about 7 years ago
Gotta get me one of those

Very steamy theme and story line. Wanna be him, or maybe even her.

AnonymousAnonymousover 7 years ago
hard

I laid playing with myself it was so sexy and provoking😙

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