tagTransgender & CrossdressersSissy Wants Her Wife's Boyfriend Ch. 01

Sissy Wants Her Wife's Boyfriend Ch. 01


I knew that my secret sissy life was about to be exposed.

Cindy, my wife, had been dating real men since my hormone therapy had rendered my sissy clit useless to her, but she was still trying to keep our "unique" marriage hidden from friends and family.

Two months ago, Cindy said, "I'm tired of trying to keep your transition a secret Arlene. I'm not going to out you to our friends and family, but I'm not going out of my way to hide you anymore either."

She also told me that she really liked Ty, the guy that she went out with the night before. Cindy said she would be bringing him home to meet me that evening after work.

"Don't worry. I've already explained your transition to him, and he is not intimidated by you at all." She explained.

She said that if everything worked out the way she had planned, he would be staying the night, and told me that I needed to put clean sheets on our bed.

"While you are changing sheets, go ahead and put clean sheets on the spare bed too. If Ty stays, you're gonna need a clean bed sweetie." Cindy said.

Although we both figured this day would come, up to this point, we had slept in the same bed since our wedding night. Even after her dates, when/ if she came home that night, we would still sleep together.

So I was kind of depressed while making the bed that I would probably be sleeping in for the first time.

Well, he did stay that night, and every night since then.

Cindy was right too. As soon as I saw him, I knew why he was not intimidated by me. He was huge. He towered over me by at least a foot. He had my sissy frame beat by at least a hundred more pounds of sheer muscle.

He was also black, which to my knowledge, was the first black man that my wife ever dated.

Ty was hung like a mule too. I saw that fact the next morning when he walked into the kitchen, butt naked, while I was eating my cereal. His semi-erect cock was as big around as my wrist, and as long as my forearm. Even before the estrogen shrank my boi-bits, my little sissy clit could never have competed with his manhood.

He caught me staring at it, as he was drinking from the milk jug, snickered, and said, "Stop drooling gurl. This cock is for your wife, not for her sissy bitch husband."

I almost died from embarrassment. I hung my head and started to cry when I realized that I was jealous. I wasn't jealous of him taking my place with my wife. Sadly, I was jealous of my wife getting fucked by this stud, and I wasn't getting fucked by any stud.

Cindy came in, saw me crying, and saw his smug look, and lightly scolded him, "Take it easy on her Ty. She needs a little time to adjust to these new living situations."

That scolding didn't do any good, because he found every opportunity to let me know that he was making my wife scream with pleasure every night.

He would even sit in the living room, while she was at work, and stroke his massive cock while watching THEIR homemade porn. Apparently, they set up a camera in OUR master suite.

I complained about this to Cindy once, but she just giggled shyly, and said, "Just watch what I do in the video honey. Someday you may be in my shoes, and need a few pointers. Arlene, you don't have to watch him stroking his cock. Just watch what I do, and you might learn something."

Each day it would be a different video, and each day, he would tell me to sit and watch TV with him.

Ty had figured out that I was mesmerised by his beautiful black cock, and I would never say no to watching him stroke himself off.

I would watch them have sex on TV, but I spent just as much time watching Ty stroking his massive meat. He knew it too, and he quickly became a true exhibitionist.

The first few times he caught me looking, I quickly turned my attention back to the TV.

After the 4th time, he said, "Listen up Sissy, I know you want my cock just as bad as your wife does, but I don't do sissies. I will however, let you move over here beside me so you can watch me stroke my cock, and watch me fuck your wife on TV at the same time."

I should have resisted, but the next thing I knew, I was sitting right next to Ty on the couch. I was watching the pre-cum form at the tip of his cock, and my little sissy clit was starting to make a wet mess in my panties.

That's when Ty started his dirty talk. "Watch what I do to your wife right here," or "Look at how much your wife loves sucking my cock. I bet you'd like to suck it too."

I would drag my attention away from Ty's pre-cum covered cock, just long enough to watch what he was pointing out on the TV, and then shift my attention back to his delicious looking cock. It was so close I could smell his musk.

I desperately wanted to taste his cock and he knew it, but he was true to his word about not doing sissies because he never made a move on me.

Ty did however, let me be a true Sissy through all of it and said, "I'm going to cum on that coffee table. Then I'm going to go clean up in the bathroom. I don't care how you do it, but I want that mess cleaned up when I get back." About three minutes later, he leaned forward to do just that.

I could not help myself. I found myself scrambling to the other side of the coffee table, on my knees, so I could watch it more closely as he exploded.

The first blast of semen, shot from Ty's beautiful cock, and landed only inches from my face on the coffee table. I felt my own clit gush a little in my panties. I lost my senses as I watched him pump copious amounts of semen into a massive puddle right in front of me. The intoxicating aroma of his seed, combined with the delicious looking puddle, was more than I could bear. I found myself leaning closer to the growing puddle.

That puddle possessed me. I had to get closer. I had to touch it. I had to taste it!! I heard him laughing at me as my lips and tongue began slurping a real man's semen into my mouth for the first time, but I did not care.

In fact, all my senses went into overdrive as soon as my mouth was full of Ty's cum and my nostrils was full of the scent of his sex. I even felt the last two splats of his semen land right on my face. Then my whole body started shaking as I flooded my panties with my own sissygasm. At that point, I knew I was his bitch even though he would never fuck me.

"Too bad I ain't into Sissies," Ty said as he was shaking the last few pearly drops of goodness off of his manhood. "Because you are one naughty gurl." Then he walked to the bathroom, as I continued to lick up every delicious drop of Ty's creamy seed.

From that day forward, I began to push the boundaries, and Ty let me. As long as I never pulled out my sissy clit in front of him, I could do just about anything I wanted.

Every day started the same way. They would both come out of "their" bedroom, usually butt naked, and eat the breakfast that I had prepared for them. Then Cindy would get ready for work, while Ty read the paper, and I cleaned up their mess.

Once she was ready for work, Cindy would come in, give me a peck on the cheek, and whisper, "I love you Arlene. Be a good girl while I'm gone."

Ty would then walk her out to her car, where Cindy would kiss him goodbye properly. Neighbors be damned. I guess she wasn't lying when she said that she was not going to try to hide our unique relationship anymore.

Ty would then lay back down for a few hours while I tidied up the house. Then I would shower and make myself as pretty and sexy as I could.

3 days after my first taste of a real man's cum, I had decided that what is good for the goose, is good for the gander. I wanted Ty and could not have him. So I was going to make him want me, even though, "he don't do sissies."

I have this nasty little schoolgirl uniform (which is actually what started my transition but that is another story for another time) that my wife talked me into wearing to a Halloween party when we first got together. I decided it would be the perfect outfit to temp the untemptable.

I went all out with my tuck, and used skin friendly adhesive to form, and hold, a vagina looking tuck in place. When I was done, the only thing that was sticking out of my "pussy lips" was the very tip of my clit so I could pee.

I pulled my white cotton panties up my creamy smooth thighs and into place. Looking in the mirror, I was very pleased with the smooth look. You could not tell that I was not a natural woman.

I then put on a white lace push-up bra that pushed my hormone-induced breasts up into a b cup. It really pushed my girls together and it would show the perfect amount of cleavage/ lace when I tied the bottom of the schoolgirl uniform blouse together.

I finished getting dressed and looked in the mirror. Perfect! No matter how I turned, my (innocent-looking) white, cotton panties were playing peekaboo from under the hem of my super short skirt.

I then pulled my hair up into little girl pigtails, on each side of my head, and secured them with puffy white bow scrunchies.

Then i did my makeup as slutty as I could and still keep a little innocence.

"I'm as ready as I'll ever be," I decided. Then I sat in my room with the newest issue of Cosmo, and waited.

15 minutes later I hear his booming voice yell, "Get yo ass in here, Sissy!"

You should have seen the look on his face when I came skipping into the room, jumped on the couch, and snuggled right up next to him. My smooth crotch under my pretty panties was on full display.

"What are we watching today?" I chirped innocently.

Ty was speechless, which did not help my anxiety. I was so nervous I thought I was going to wet myself.

"What if I push things too far or too fast? What if he pushes me away? What if he DOESN'T push me away? What am I doing? What am I going to do?" All of these questions were running through my mind when Ty finally broke the silence.

"Oh my... You look... Uhhhh... "

"Cute as a button for a sissy, or downright sexy for a sissy! Right?" I interrupted a little more sharply than I intended. In fact, I sounded downright angry. That snapped him out of his daze.

"I was going to say that you look like a naughty school girl that needs to be spanked before I got so rudely interrupted! What got your panties in a wad all of a sudden?" Ty snapped back.

I couldn't resist. In my best little girl voice, I playfully teased, "My panties are not in a wad. See?" I spread my legs wide to show Ty my pretty, panty covered "cameltoe".

He stared, speechless again, as I traced my smooth camel toe with my red fingernails. Then, just for good measure, I stood up and turned my back to him. With my legs spread wide, I lifted the hymn of my skirt to my waist to show Ty that indeed, my panties were NOT in a wad.

"See... No wadded panties here." I teased innocently. I twisted my hips from side to side, like an antsy little girl, so he could get a good look at my cute ass.

I sat back down, pulling my feet under my right side, which forced me to lean on him. I could see that my teasing was having the desired effect because Ty was already pulling his hardening cock out of his boxers and the movie wasn't even started yet.

As soon as I saw Ty's cock again, those familiar urges to fall to my knees and wrap my painted lips around the head of his cock, came flooding back in stronger than ever.

I took a tiny leap of faith and laid my head on Ty's shoulder so I could watch closer as he began to stroke his cock for me. When he did not push me away, my heart leapt with joy.

"Too bad you're not into sissies," I purred, just loud enough for him to hear.

"Huh? Why?" he asked.

I lifted my head from his shoulder, looked him straight in the eye, and said, "Because if you were into sissies, we could be making our own movies. But since you are not into Sissies... "

I let my sentence trail off and started reaching over him to the drawer on the end table. "Accidentally," my boobs scraped over the top of his cock on the way.

"Oops. Sorry, I just need to get something out of this drawer," I said. I stretched further than I needed until I felt Ty's cock slide against my bare belly. A light moan escaped his lips, and I had to turn my head away to keep him from seeing the grin on my face and the desperation in my eyes.

I desperately wanted him to grab me and rip my clothes off, but Ty wasn't quite ready for that, and I knew it. I still needed to work on him a little.

I grabbed the handbag I was looking for, closed the end table drawer, and reluctantly leaned back to my place beside him on the couch.

I felt the slick wetness of Ty's pre-cum on my tummy where his cock had been touching me, and noticed that he was staring at it. Seductively, I took my red tipped finger, scooped his pre-cum from my baby smooth skin, and while his eyes were locked on me, I licked that finger clean.

"Mmmmm. Too bad," I mumbled.

Ty turned his head away quickly, like a kid that had just been caught, by his Mommy, doing something that he should not have done.

"Are you ever going to start the movie?" I asked, as I rummaged through my bag.

"Huh. Oh yeah. Here," Ty stuttered as he started the movie, but most of his attention was still on what I was doing.

On-screen, my Cindy was giving Ty head, but sitting right next to him, was a very willing Sissy rummaging through what can only be called a bag of sex toys.

I soon had all of Ty's attention when I started pulling out this dildo, and that vibrator, and laying them on the couch beside me.

After taking more time than I needed to find what I was looking for, I finally pulled out my big black dildo, looked Ty in the eyes, winked at him, and seductively licked the tip of it.

His eyes went wide.

I giggled, then jumped off the couch and went to the end table.

"Since you aren't into Sissies, I guess I have to get my BBC this way," I said. Then I proudly stuck it to the end table, squatted down, and boldly proceeded to suck my big black cock.

I glanced over and saw that my plan was working. Ty had completely giving up the pretense of watching their infidelity on the TV, and was focusing all of his attention on the show right next to him.

Ty was rapidly stroking his massive cock and from the looks of the string of pre-cum hanging out, he wasn't far from exploding.

I had practiced a lot, and there wasn't a dong in my bag that I couldn't deep throat with ease. I relaxed my throat, and took the whole shaft down. My nose bumped the table, and I pulled up to the tip, and then did it again.

I heard Ty groan loudly and knew it was time to make my next move. I quickly pulled off of the dildo, and spread out on the floor in front of him.

"I'm tired of cleaning the coffee table, why don't you just cum here instead." I whispered seductively, as I pointed to my hungry, open mouth.

Ty was beyond the point of return, and I was between him and the coffee table, so he straddled me and gave me what I wanted.

I was astounded. I didn't think he would do it. When he did, I found myself, lovingly, caressing his thigh as Ty emptied his hot, manly seed into my hungry mouth.

Ty was mumbling stuff like, "You slut!" and, "Drink this you bitch!" As he finally shook off the last drops into my mouth, Ty said, "I hope you like it, because you are going to be my daytime cum slut."

I didn't like it. I loved it! I loved the smell, the taste, and the hotness of Ty's semen coming straight from his cock to my mouth. It was sooooo much better than licking his cooling puddle up from the coffee table.

I came as I looked Ty in the eyes, and greedily swallowed his load.

After I came down from my sissygasm, I seductively licked my lips clean. Still staring at his post orgasmic face, I smiled and said, "Honey, you can put your cum in me anytime, or anywhere you want."

After that day, I continued to work on Ty with all of my sissy power. I pushed him further down the rabbit hole. I wanted Ty to admit that he was indeed, "into Sissies," and I was determined to push as hard as it took to accomplish that feat.

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bySissyArlene© 7 comments/ 24286 views/ 47 favorites
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by Anonymous

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by fermat02/17/19


This is a really good story, beautifully paced and well written High octane filth! I usually prefer the sissy to be more reluctant, but in this story the fliritness and 'wanting it' really works. Lookmore...

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by stacejo11/14/18


More More.....

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by SissyArlene08/11/18

Thanks for your nice comments gurls. It makes me want to start chapter 2 as soon as I can. I was expecting my first story to flop and I wouldn't have to write chapter 2, but y'all have showed nothing butmore...

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by latinarita308/09/18


Can't wait to read the next chapter, love how you built the story up slowly

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by BrendaNW08/09/18

hot ..

Very hot I couldn't stop reading .. Oh, I do think the wife overplayed her hand .. since the husband is transitioning then she is now no longer really a sissy / CD but much closer to being a woman ..more...

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