Pretty boy to Sissy girl Ch. 04

Story Info
Pretty boy and wife get gang banged.
3.7k words
4.71
36k
51

Part 4 of the 4 part series

Updated 06/12/2023
Created 07/25/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
moonsissy
moonsissy
250 Followers

It had been over a year and my sexy wife Tara, was still having an affair with her very masculine lover, Michael. Sometimes they would let me join in the fun. On those occasions I was always there to help pleasure Michael and I was always expected to lick his sperm from my wife's pussy at the end of their love making.

On the times when I wasn't allowed in the bedroom with them, as Michael and my wife immersed each other in sexual bliss, I was still expected to clean up the cream pie that he deposited in Tara's pussy as he watched. I was more than willing to do so. He was the dominant, masculine black alpha male and I was a little white fairy. I was a willing cuckold sissy, dressed in lingerie and wearing makeup, and as femme as I could be. It totally excited me that a real man, a powerful black man was passionately satisfying my wife and himself in our bed. When they first started to have their affair I must admit, I was a little jealous and felt inadequate as a man. But I was inadequate, with my lean, fem body, my soft pretty features and of course my tiny dick. I soon realized my weaknesses as a man were my strengths as a a fem sissy. I much preferred being fucked by a man and and knowing he was satisfied than fucking a woman and leaving her unsatisfied.

At times when Michael came over to our home he would tell me I had to sit in a chair outside the bedroom door and listen to them as he gave her orgasm after orgasm. Sometimes he had me sit in a chair in the room and watch as he did things to Tara which I was too fem and too small to do to her. His big black dick hitting spots I could only dream of as his muscular frame held her in positions that were beyond my strength. I would sit there in that chair, rubbing my swollen little sissy dick as if it were a clit in my panties. In truth I was wishing Michael would hold me in those positions and fill me up with his big dick. I wanted to be filled with his sperm. Occasionally he would do me like that and I loved it. He always fucked me to orgasm after orgasm. Tara would watch and make comments about Michael being so amazing and what a hot fem bitch I was. She often would tell me, when Michael was in the same room she never thought of me as male in anyway. She truly thought of me as another woman.

When Tara and I would have one on one sex, it was usually oral or strap-on sex.. My little white sissy clit wasn't going to satisfy her and we were both fine with that. Tara and I would kiss passionately. Our lipsticks mingling and our fingers roaming. We would actually rub clits together like two lesbians, which we both liked. And often I was the one getting fucked by her as she donned her strap-on and screwed me until we were both screaming with intense orgasms.

On those evenings when Tara and Michael would go out on a date, I would be at home waiting with my tiny erection snug in my g-string or other variation of sexy panties, knowing that Tara would let me lick her sperm filled pussy when she got home. I loved tasting Michael's seed mingled with my wife's juices. I loved how she would hold my head in place and tell me all about what they did as I went down on her pussy. I would be rubbing my 4 inches and trying not to cum until she did.

Whenever they were on a date together I would spend the evening dressing up and doing my makeup. I would often play with our dildo collection. When I knew Tara was out getting fucked by Michael I was a cat in heat. I'd have a dildo inside of me fuck hole and I'd be sucking on another. I would try to save my orgasm for when Tara returned and fed me Michael's cream from her pussy, but it was hard not to cum when I was riding a dildo and sucking wantonly on another.

I was always dressed fem and sexy in Michael's presence and it was getting to the point where Tara liked dressing me up even when Michael wasn't around. She said it was fun having me as a girlfriend to talk and do things with..

Tara also liked that we could go shopping together. We both loved fashion and shoes and sexy lingerie. I had gotten to the point that I loved being dressed as a woman and I was preferring my feminine side. I loved all the things I did that made me feel womanly. It was to the point that Tara only called me Steph, or Stephanie and I was so comfortable with that.

I also liked when we were both dressed up in sexy lingerie and my wife confided in me about her deepest and most erotic sexual fantasies. When she was helping me with my makeup and we were choosing what dresses we'd wear, it was so easy to open up about my own desires. There were no inhibitions. I could talk about how I enjoyed being one of Michael's girls. We would both giggle as we talked about how big his cock was and how we both got so excited whenever he was around. These were things that I wouldn't be comfortable talking about as a man. I would tell her how much I enjoyed being a cocksucker and how much I loved being filled with a hard dick and taking a man's load down my throat or up my ass. And how I enjoyed being submissive.

So this one day as she and I were modeling dresses for each other, Tara started saying how much she fantasied about being gang banged by three or four, muscular men. How much she wanted to be filled with big cocks, one in each hole and one in her hand.

"Wouldn't that be awesome?" she said, "I know I get to suck on your cock hon, while Michael fucks me but it would be really hot to have a big cock in my mouth while being fucked by a big one."

Her words would have stung a year ago but I completely understood. I knew my little sissy dick wasn't going to satisfy her desire for a man's cock. I knew she loved me and found me sexy for many other reasons but my little penis was not high on the list. I now find it funny that I once thought my little thing was average size and would be satisfying for women. When I realized I was really tiny it hurt at first. Now I am so happy that I am small. I know my place. I was far from some alpha male. My place was now giving pleasure to alpha males and being a cuckold to my hot wife.

"Oh love, I agree with you 100 percent," I enthusiastically urged her on, "and could you imagine having a third dick up that hot ass of your's? I would love to see that. I am getting so excited for you. Hell I want to be stuffed with big cocks too! I'd like two black men using me as their white sissy bitch while you are next to me getting gang banged."

"Oh fuck, you are a dirty girl, Stephanie! You know I love that about you." Tara pulled me in and kissed me. When she pulled back from my lips she said, "We need to make this happen, and I know how. I met one of Michael's single friends, Trevor, awhile ago and when Michael wasn't around, he said to me, that he would love to fuck me but he knew Michael wasn't the sharing kind. He also said that unlike Michael he'd share me. He said a sexy woman liked me should be appreciated by more that one guy. I joked that my husband felt the same way. He gave me his number and said if I ever wanted to get together to call him. We can call and see if he has some sexy friends he'd like to share us with. What do you think?"

I felt a wave of heat flow over me. My little dick was rock hard in my panties. I had a great desire to be taken by more than one man at a time, but fantasies are safe. The reality was scary but so tempting.

"I don't know," I stammered, "How would we know if they would be comfortable with a trans girl like me? As exciting as I find it, it is scary."

"Well Trevor thinks you're hot, so I'd ask him to get guys who would be into you, also."

"What do you mean he thinks I'm hot? How does he know what I look like?"

"I showed him some pics of you and a video of you sucking on Michael's cock."

"What? Oh my god..." I didn't know what to think. I was petrified that my wife was showing pictures and videos of me to strangers, but at the same time I was still rock hard.

"Honey, I am proud of you and who you are. When I mentioned I had a husband who liked to share, he was curious about you. When I showed him your pictures he was really impressed. I told him that you loved BBC as much as I did. Then he said, he thought you were one of the pretties white sissies he's ever seen and he'd fuck you in a heart beat."

"Wow, he really said I was one of the prettiest he's ever seen and he'd like to fuck me?"

"Yep. Then he said, he bet you have a tiny pink clit. I said yes but it is so pretty. He said it all makes sense and that you looked like a natural born cocksucker in the video."

"Oh my god, oh my god, " I squealed.

"Hon, it's all good," Tara said as she slipped her hand under my dress, "Oh my god is right! Your little dick is as hard as stone. Let me help you with that."

Tara got on her knees, pulled down my panties and put her head under my dress. She slid my hardness between her lips and began to bob up and down. Just as I was about to orgasm she stopped and asked, "What do you think hon? Should I plan a gang bang for us,"

How could I say no, I was so aroused at that moment. As she was sucking on me all I was thinking about was the two of us filled with big black cocks, "Oh yes, for sure," I replied. She took me back into her mouth and I came in seconds. She made sure I had emptied my cream into her mouth. She stood up and kissed me. She fed me my sperm. I swallowed with great lust.

"My horny sissy husband was craving seed. Don't worry love, we will get a lot of sperm for you to enjoy soon.

Tara arranged things very quickly. In less than two weeks we were dressed up like two beautiful lingerie models and strutting around this large hotel suite in our fuck-me pumps while sipping a little wine and waiting for the room to fill up with hot, muscular black men.

The first to arrive was Trevor and his friend Troy. I greeted them at the door.

"Well, you are hotter in person," Trevor said as he looked me up and down like a hungry wolf sizing up it's prey, "We are going to do some breeding tonight."

"Where's the sissy bitch, Trev? I am in need of a bitch's mouth right now," Troy said as he looked past me.

""This is her standing in front of you," Trevor laughed, "I told you she was a fem thing."

"Damn, you weren't lying!" Troy said as he stepped closer to me.

Trevor made his way over to my wife and they had no hesitation. They just started kissing and touching.

Troy looked at me and said, "well girl, what are you waiting for? Get me a beer and then you can undo my pants. I'm here to party."

I did as I was told. I wiggled my ass as I crossed the room to get a beer for this black stud. When I returned he had already removed his shirt to reveal his taut, muscular physique. My heart was pumping fast as I looked at this beautiful dark skinned man who was waiting to have his cock pleasured by me. I handed him his drink, dropped to my knees and began to undo his belt and open his pants. I freed his fuck pole from his underwear and I felt like I was drooling, I was so in lust for it. It was big and thick and dark chocolate in color.

"May I taste your big dick, sir?" I asked as I looked up at this muscular, gorgeous man.

"I like that you know your place, bitch," Troy said, "First tell me how much you want this big black dick."

"I'm craving your dick so badly. The minute you walked into the room I knew I wanted to be on my knees sucking you off and getting fucked like a bitch in heat. And now that I see it, I lust even more for it."

"Oh yes, I love you white sissy cocksuckers. Go on, suck it bitch." I gladly took the head in my mouth. it was so big and delicious. I loved its scent and its taste. I could already taste and feel his pre-cum. As I started working it slowly into my mouth Troy put his hand on the back of my head.

"Are you one of those sissy white whores who has a tattoo of a black spade with the words 'black owned' underneath it? I bet you're one of those little sluts that only want black meat. When you and your hot wife have sex I bet all you're thinking about is black men using you. Right cocksucker? You white sissies are really great cocksuckers. With your little pink dicks you know your place is serving black men."

I couldn't answer with my mouth stuffed, but most of what he said was true. I nodded my head. I liked hearing him talk nasty as I blew him. I was almost hypnotized by his deep voice and his thick dick. I didn't even realize that there were other men in the room now until I felt hands on my ass. And a cock slap up against my face. I continued bobbing up and down on Troys hard rod I stroked another cock and felt it stiffening in my had. I felt Troy put both hands on my head. I knew he was going to deliver a warm treat down my throat. I felt a wet finger start to play with my asshole. I moaned as it began to enter me.

"Oh, fuck bitch, I am going to cum," Troy grunted, "swallow it all slut." And I did. Spurt after spurt of thick sperm flooded my mouth and throat. At the same time I was getting finger fucked. I thought I'd orgasm any second. When Troy finally withdrew his spent meat from my mouth I bent over with my head down and ass up. That finger was replaced by a thick dick which began to take me hard and steady. He grabbed my hips and thrust deep. In and out, a rhythm that had me feeling waves of pleasure and apparently he felt them too because he quickly came inside me..

"Fuck that is a tight white ass," the stranger said as he slowly pulled his dick from me. I finally got a chance to stand up and see a room full of men. Some already naked. I smiled at the man whose cock just filled my ass with his seed. I could feel is sperm trickling down my leg. I saw Tara on the bed being fucked doggy style by a good looking guy while sucking on another man's dick. I made my way over as guys stood naked around Tara, stroking themselves.. They touched me and said things to me but I wanted to get to Tara. I knelt down by her and whispered in her ear how hot she looked and I kissed the side of her cock filled mouth. I then climbed on the bed next to her and offered my ass and mouth to whomever was there. In no time at all my mouth was stuffed and someone was behind me sliding a hard cock in my already cream filled sissy pussy. Still I flinched at the size of whoever was entering me. It felt like a baseball bat. I moaned in pain and pleasure as these man fucked me from both ends. I don't know how much time passed as another stud came in my mouth and someone else took his place. The baseball bat continued to abuse my ass with my consent. I couldn't help but orgasm as I was being drilled by this massive dick. My sissygasm shot all over the bed. I was seeing lights and stars as it brought me to another world.

As I regained my senses, I looked up to see Tara was no longer in the bed. She was across the room now being held by this tall bull. Her legs wrapped around him. She was already impaled on his dick and anther guy was behind her. I could see him putting lube all over his big hard prick. He closed in and started to slowly enter her ass. At this point the guy with the huge pole who had brought me to orgasm pulled out of me, His cock still hard as he stood in front of me. I realized it was Trevor. It was his big pole that had just brought me to ecstasy.

"I loved fucking your ass pretty sissy, but I've been waiting all week to fill your lovely mouth with my seed. Get on your knees, time to worship my big dick."

I was now on my knees with Trevor's hard cock at my mouth and two guys standing around me stroking their beautiful monsters. As my heart pounded and my dick was throbbing again, I began to slowly take that chocolate treat into my throat.

"Oh I knew you were going to be a good cocksucker the minute I saw that video of you sucking off Michael," Trevor moaned, "You white sissy bitches just love sucking black dick, don't you?"

I could only nod my head in agreement as I took that big rod deeper into my throat. I reached over and took another man's cock in my hand. It felt so thick and I stroked it. The experience of stroking a real man's big cock is so different than stroking my own little thing. To stroke myself I use a couple fingers and don't have far to go with my stroke. With this BBC in my full hand I had a lot of movement to go back and forth. It was always so intoxicating.

Trevor slid his cock down my throat. He had just fucked me to orgasm and I wanted to give him the pleasure of filling my throat with his sperm.

"Come on you sissy bitch, take it down that hungry throat," The first guy I sucked off was now standing next to Trevor and me, egging me on. " You fucking white sissies are such great cock suckers. Did you see your wife taking all that cock sissy? She knows how to please men, show us you can please real men too. Look at your tiny pink clit. It's all swollen with excitement. Lets see if you can cum for me." With that Troy reached into my bra and took my nipples between his fingers and played with them. Trevor was fucking my face. I was so hot. I could see guys standing over me, stroking their big beautiful cocks. It was so erotic, all these big beautiful black men using me and my wife for their enjoyment. All of a sudden one guy stepped closer and came on my face and in my hair. Troy continue to tweak my nipples. I could hear my wife moaning in pleasure and begging to be fucked harder. The excitement got to me and I had another orgasm. I was gagging on the big bat in my mouth and moaning and squirting as cum ran down my face. Then I felt Trevor pull my head in and he started to cum. I was trying to breathe with this big dick in my mouth, my nipples now super sensitive as I continued to orgasm, and Troy continued to pinch them. It was all so intense and exciting and erotic. Troy was calling me white sissy faggot, and cum slut and whore, which intensified my orgasm.

I'm not sure how many more studs came on my face but it felt so sexy to have another load splash on me.

When Troy finally pulled his dick from my throat, I gasped for air. I laid back against the bed. My mascara was running from my tears and from the cum dripping off my face. I saw my wife getting off of two men who had been filling both her holes. She slowly walked over to me and knelt over my face.

"Lick my cum filled holes my sweet bitch," She said as she pulled my cum covered face into her. I gladly lapped up the sperm that dripped and oozed from her ass and pussy. As I licked Tara another stud came up behind her and easily slid up her cum filled ass and began to screw her, I licked at her pussy and his balls, I managed to see she already had another prick in her mouth. I took a moment and thought how thankful I was that the night had plenty of hours left.

moonsissy
moonsissy
250 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
cdCindy1cdCindy15 months ago

Yes yes YES YES !!!! I too want to be a white sissy faggot bottom bitch slut with my wife, both of us serving a room full of BBCs.

AnonymousAnonymous5 months ago

Omg just rubbed my little sissy cock and had a little cummies on my fingers and licked them clean to this I wish that was me ,kisses from Laciebree

AnonymousAnonymous7 months ago

I have just read the whole series again and I love it, I dribble my cummies in my panties just reading it xxx sissy Lucy

AnonymousAnonymous9 months ago

Great story I love it being trans 😂😂 spit roasted by cocks even two cocksup my ass pussy at the same time

JackiemichelleJackiemichelle11 months ago

Great story. I couldn't stop reading. I wish I was her and could serve all the BBC I could. Love your stories

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Barbie's BBC Beginning A sissy husband gets roped into interracial sex by his wife.in Transgender & Crossdressers
Dream Girl Pt. 01 Get the girl... or become a girl for BBC.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Barbie's BBC Awakening A sissy husband's journey to becoming a BBC slut.in Transgender & Crossdressers
My Wife's Wife My wife makes me her wife with help from bff and lover.in Transgender & Crossdressers
More Stories