Sissy Bottom Has a Nite Out Ch. 03

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More cross-dressing fun with buddy & wife.
3.7k words
4.49
109.9k
31

Part 3 of the 4 part series

Updated 10/31/2022
Created 09/15/2005
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After two wild and raunchy nights at the local ABS with my fuck-buddy Eric, I still had one night left while my wife was out of town. Eric and I were both pretty whipped (and sore) after the previous two nights play, but opportunities like this only come up so often. We had gotten in late from last nights adventure and crashed in my bed without even showering first.

I awoke in morning to the sound of the phone ringing next to the bed. It was my wife Toni checking in and letting me know that she would be home early tomorrow morning. As I talked to her, I looked over at Eric, only to find him lying in bed next to me, sniffing the cum-soaked lacey panties that we had both worn to the adult theater for the last two nights.

As I watched him, he deeply inhaled from the many cum stains on the satiny fabric while he slowly jacked his raging hard cock. I love his cock. It is 8 inches long, with a nice blue vein running down the top, leading to a bullet shaped purple head that curled just slightly upward from a ram-rod straight shaft. His meat was pretty thick, probably two inches across. His cock was the first part of him that I met a few years ago, through a glory hole. He was the first man who really fucked me in the ass.

"Uh huh, okay...love you too." I told Toni "See you then. Bye."

I had a hard time concentrating on my conversation while watching the hot sight in front of me. Eric was jacking on his cock while licking and sniffing the several loads of jizm. I could see that he still had a lot of cum still crusted about his body -especially on his chest- where many men had unloaded on him last night.

It was a hot sight, let me tell you. I could feel my own cock stiffening up under the sheets as I watched him masturbate. I especially loved how his pink tongue flicked out to lick at the still-wet spots on those panties. I could remember wearing them myself when I shot my own load into them two nights prior.

"You look hot, man." I breathed to him. "You want some help with that?" I nodded my head at his throbbing erection.

"Yeah, suck me." He replied.

I slipped out from under the sheet and climbed between Eric's spread-eagled legs. My own cock was now completely hard, forcing me to remain on my knees, with my ass pointing up in the air. I reached out and grasped his shaft. The feel of his steely-soft manhood in my hand immediately raised the heat in my own loins.

"Mmmm." I moaned.

Then I leaned forward and steered his dick into my mouth. Slowly, I slathered him up, making his shaft nice and wet. Then I began giving him head, using my hand to stroke his slick shaft, while I used my steamy hot mouth to work his throbbing mushroom head. In no time at all he was moaning through the cum-stained fabric of those nasty panties.

"Yeah, man. That's good. That's real good. Suck me. Ohhh! Take my load. I want you to feed me my own cum. Make me cum and spit it in my mouth." Eric said.

"Mmmppphhh." was the only reply I could cum up with.

His cock filled my mouth tightly. I could taste the palate of fresh pre-cum and last nights cum-fueled-debauchery mingled on his fuck-pole. There was no way I was coming off of that cock for something as useless at that moment as speech. I bobbed my head up and down, jacking him off. My spit made his crank nice and wet, and I was really going fast with my blowjob. I wanted his load in my mouth quickly, I was so turned on.

"Awww Fuuuuck!" Eric said "Here it comes, here it comes...take my load, fucker. Eat my cum!!"

With that, I began to feel his cock pulsing, as blast after blast of his watery spunk gushed into my hungry mouth. I wanted badly to swallow it, but did not. After his orgasm subsided, I crawled up Eric's body and leaned down to his face. He looked up at me and slightly opened his mouth. I leaned down to kiss him and as I did so, I opened my mouth and let his seed slowly dribble out of my mouth and into his. When he had gotten about half of the load, I leaned all the way down and kissed him, using my tongue to push the last of his cum into his mouth.

While we kissed Eric grasped my cock in his hand and began to furiously jack me off. In no time at all I was ready to blow. I leaned back up, sitting on my heels while he pulled on my dick. I guess he could see it in my face, because when I got close to shooting, he looked at me and said:

"Here, shoot another load in these for me, baby." Then he held those cummy women's panties in front of my cock. "More spunk for me lick and sniff later."

Well, that did it, and with a loud moan/groan, I blew my load into the panties resting in Eric's palm. It felt so good that I reached out and grabbed his still-jacking hand. As I caught my breath, he smiled at me and then brought the panties to his face.

"Mmm," he said and his tongue flicked out to lap at my fresh jizz. "Yummy."

I collapsed onto the bed next to him and told Eric that the wife would be home in the morning.

"Good," He said "one more night of fun for us boys. Let's get cleaned up. I want to run to the mall."

"The mall on a Sunday?" I asked "What the hell for?" Eric just smiled slyly at me and said "You'll see."

So we cleaned up and got dressed, and off to the mall we went. When we arrived, Eric led the way, right to the Ladies Lingerie store.

"What the heck are we doing in here?" I hissed at Eric.

"Just relax and go with it." He replied.

A salesgirl came up to us, and like most of the babes that work at these places, she was looking very hot, like a high class hooker.

When she asked what we needed, Eric told her that he was looking for something for his wife (he's not married), and that I was looking for my wife too. I just looked at him with a confused look and he smiled.

"We want something sexy, stockings, garters, panties, and a bra." he told the girl.

She said "Okay." and started to walk across the store.

As we followed the girl across the store, Eric leaned in and said to me "you'd better buy Toni something to replace the stuff we used, because I ain't giving her back those panties."

"Yeah, but..."

"Here we are," the salesgirl said indicating tables loaded with every kind of women's under things ever made. "These are what we have. A lot of women like these ones here," She held up some thong panties "and if she doesn't like the thong then there are these instead...." And she went on with her sales pitch.

In the end, I bought a couple sets of lingerie in Toni's size, and Eric bought two sets of underwear, stockings, garter belts, and braziers for his 'wife'. It turns out Eric's 'wife' is a bigger woman, about a size 14, but she still had small tits, (I wanted to die; I was terrified that the salesclerk knew what was up). Then we headed back to my house.

We spent the afternoon watching some football on TV, and some porno DVDs, then after another pizza, we decided it was time to head out.

Into the bedroom we went to get ready, and Eric tossed me some things from the bag.

"Try these." he said.

I got naked and began to pull on my new underwear. Eric had bought me a pair of light blue high cut panties. I slid them up my legs, enjoying the silky caress of the material on my skin. Then I pulled them up tight and tucked my stiffening cock back between my legs. Boy they felt good. Then I took the matching garter and fastened it around my waist. I opened the stocking package and pulled out the brand new pair of real silk stockings. They were a tan color, with the seam running up the back of the leg. I rolled one up in my hands and began pulling it up my leg.

"Wow, you look good doing that." Eric said "If you're not careful I'll jump you right here."

"What would be so bad about that?" I asked as I pulled on the second stocking.

Eric had removed all of his clothes and was playing with himself while he watched me fasten the stockings to their garters. As he jacked his cock, I grabbed my new silky lace bra and put it on. There were almost no cups to the thing, almost like a training bra, and the triangle patches nestled against my chest nicely.

"I feel so sexy in this stuff, thanks Eric." I said "Now put yours on too."

"There's no way I can get this into a pair of panties" Eric said wagging his fat and hard cock at me "Why don't you come here and help me out?" He sat down on the edge of the bed.

I slid off the bed and crawled over to him. I kissed him gently on the mouth. Then I began kissing my way down his body. First I licked and sucked his nipples, and then I kissed his belly. Then I planted butterfly kisses all around his groin. Eric spread his legs open farther and lay back on the bed, closing his eyes.

When I grasped his dick in my hand and pushed it back onto his hard abs, I stuck out my tongue and licked his puckered asshole. I licked all around his ring, then I spit on his brown eye to make it wet. I gently began to jab my tongue in and out, fucking him with it. Then I began to lick and kiss his heavy balls. I gently sucked one, then the other into my mouth.

As I was about to slide his cock into my waiting open mouth, I sensed another presence in the room. I started to turn around to look when she grabbed a handful of my hair and yanked my head back.

"You fucker!" she growled, "What the fuck are you doing?"

I looked up into the enraged face of my wife, Toni. She was snarling at me. Her own beautiful face was twisted with rage as she pulled hard on my hair. Her 36 B breasts were heaving with her breath under a tight grey sweater.

"I left my conference early to come home to ... THIS!" What the fuck are you doing? Christ, what are you wearing? What the fuck..!"

Eric sat up on the bed and covered himself with a sheet. His cock was still rock hard and he was trying in vain to hide it from Toni. My cock was also staying hard as hell. I admit it, I was turned on by my lovely wife yanking on my hair, and my erect dick was poking out through the leg hole of my lacey panties.

"I...I...I..." was all I could say.

"You fucking little bitch!" She screamed at me. "How dare you do this to me? How can you possibly do this to me?" Then she wound up her arm and slapped me across the face with her free hand, while holding onto a handful of hair with the other. She drew back to slap me again, and then seemed to change her mind and instead spat right onto my face.

"You whore." She said as her spittle ran down my face. "This is what you do when I am away? You like to dress in women's clothes and suck cock? You want to be this bastard's little whore?" She said indicating Eric. "Well, fine then, be his whore! Suck on his cock. Let him fuck you in your asshole, you little slutty bitch. I don't care!" She turned towards Eric. "You get over here!" she barked.

Eric just sat there, quietly looking at her.

"I said come here!" she yelled, then with a jerk, she tossed me onto the floor by my hair and walked to the side of the bed near Eric. "When I tell you to do something, you'll do it. Since you're fucking my husband, it's the least you can do." she sneered.

Then she reached out and whipped the sheet off of Eric, exposing his throbbing cock. She reached out and grabbed him by the balls, pulling him up off of the bed. She then led him with his balls like a leash over to where I was still lying on the floor.

"You want to suck cock? Well then, suck cock. NOW! Suck his dick, you cunt!" She released Eric's balls and again grabbed my hair. She pulled me to my knees and shoved my face into Eric's groin, rubbing it around like you would a naughty dog that had been caught in the rubbish bin. His boner was slapping me all over my face while she pushed me around his groin.

"Open up, cunt." she said.

When I did she grabbed Eric's cock and held it in her hand, then steered it towards my mouth. As I took him in, she grabbed the back of my head and pushed hard forward. Suddenly, and without any warning, Eric's dick was all the way down my throat, and my nose was again rubbing his close cropped pubic hair.

I shuddered and gagged, pulling back a little to breathe, when Toni slapped me hard on my panty-clad ass.

"Sluts are supposed to like cock in their throat..." she said scornfully. Then she slapped my ass again, hard. "Try it again, all the way in, bitch."

I did as I was told and again deep throated that 8 inch cock, but this time I was ready, and took him without any problems.

"That's the way, good girl." Toni told me. "How's it feel, Eric, is she a good cock-sucker?"

"Oh yeah, Toni, the best." Eric replied.

"Not the best, Eric. Not the best." Toni grabbed my hair and threw me off his cock and onto the floor. "Go sit in the corner" she told me and I did.

Then she dropped to her knees and began sucking on Eric's cock like I have never seen her suck before. She was a woman possessed; it seemed she wanted nothing but to gobble as much of that cock as she could. She was ramming her face up and down that big fat shaft, burying her nose in his pubes while his balls bounced off her chin. She was throat fucking him for all she was worth. I could see Eric's balls begin to tighten up and I knew his orgasm was building quickly.

Toni sensed it too, and she pulled off of his dick. "Not yet you don't. Now who's the best Eric?"

"You are, Toni. My god, where did you learn to suck cock like that?" he asked (I was wondering myself).

Toni smiled at Eric and snapped her fingers at me. "C'mere. Its funny Eric asked that, because I have a little surprise for you. I came home early for a reason. I have a special treat for you, my little whore." She pulled her sweater up over her head, and dropped her skirt and panties to the floor.

As I crawled over, I could see her pussy was glistening. She always gets really wet when she's turned on. When I got closer, she snapped her fingers at me again.

"Sit" she said, and I sat back on my heels.

Then she walked over to me, grabbed the back of my head to lean it back slightly, and shoved her pussy onto my mouth. "Lick it out, pussy boy."

I began lapping at her pussy and it hit me almost immediately, her pussy was full of cum!

When she saw the realization across my face she said "That's right, faggot. Eat all that hot cum out of my juicy pussy. That's a fresh load just for you. Dave from work just fucked me in the backseat of my car not more than 20 minutes ago. He has such a big cock. I bet you wish you could suck on him too, don't you?" She shook her head scornfully. "Well, eat his load from my pussy, get me nice and clean. Eric, you fuck him in his little pussy boy ass, now."

Eric came around behind me and grabbed the waist band of my panties. As I sucked that salty musky load from Toni's hot snatch, he yanked them roughly down. Then I felt the cool squirt of the lube on my asshole. Then he rubbed his rubbery cock head around my pucker a couple of times, and then shoved it all the way in with one hard thrust.

My scream of agony was muffled by my wife's cum dripping pussy resting on my face as she stood over us. Eric never let up, and began to fuck me hard and fast. Soon my own pain switched to pleasure as he pounded in and out of my man-pussy. I could feel his hands as they rubbed my bra covered tits and his thighs were rubbing on my silk-stockinged legs. Fast and hard he pounded me. He wanted to cum bad, and I wanted him to.

"Ride that cock, pussy boy." Toni said. "Feel him fill your ass with his cum." She yanked my hair and ground my face into her sweet and tangy pussy. "Eat me". She said.

Eric's 8 inch fuck-pole continues to pound my greasy assshole, and I loved every thrust. I could hear the squishing noises of the lube as his balls slapped my own fully loaded nut sack. I greedily lapped at Toni's pussy, which by now was pretty much cleaned of the load of cum that was there earlier, but I was still enjoying the taste of my beautiful wife's dripping snatch. I was totally aroused by the mental and physical stimulation I was receiving.

I watched as Toni's hands played with her nipples, tweaking, pinching, and pulling the pink buds. She was moaning loudly, and she arched her back, snapped her head back and squeezed my head between her thighs with a vice-like grip.

"Oh God! Oh Jesus! Oh fucking Christ YES!" She exclaimed. "I'mmmmm Commmmming!!!"

Her body writhed above me, as she was overcome by a powerful orgasm, and as I licked at it, her pussy became even wetter with her fresh squirt of her cum.

Toni backed away from me, spent, and fell onto the bed. As she laid there watching us, she asked Eric "Does it feel good to fuck his little asshole? Is he tight? I know men like their pussies to be tight".

Eric continued to fuck my ass, but as Toni was talking to him, the pace quickened, and I knew his own Orgasm was imminent. Toni was playing with herself as she sat there watching and listening to us.

"Oh Toni, his asshole feels so good on my cock. I wish you could feel this, baby. He is such a good little whore. You should have seen him the other night. I bet he fucked and sucked 10 guys off. Did you know he likes cum that much. He does like cum, don't you, faggot." Eric slapped me on my ass.

"Yes! Yes, I love cum; I want to eat your load now, Eric. Please." I begged.

"Okay, slut. Get ready, because here it comes."

With that, Eric pulled his big cock out of my ass. I spun around to face him and he grabbed my hair with his left hand. As I opened up my mouth he jerked my head forward and buried his cock in my face. He throat fucked me hard for maybe 30 seconds, then I felt his cock head swell, and his cum flooded my mouth. I hungrily gulped and sucked at it, making sure to swallow every drop. When he was done shooting, Eric pulled out of my mouth and wiped his crank on both sides of my face.

"Good slut, that was good." Toni said. "Now, come here." She patted the bed next to her. "Lay down."

I did as I was told, and lay down on the bed next to her. She looked at Eric and beckoned him over to us.

"Jack him off." She told him. "Make him shoot his dirty spunk all over his pretty ladies clothes."

Eric grabbed me, and began stroking my stiff cock. I was so turned on; I knew that I wouldn't last long at all. After only a few rapid strokes by Eric's hand, I felt my balls boiling over, and my cum began to spew from my cock in long steamy ropes. The first blast landing on my chest and face, the second right in the crotch of my panties. Then Eric aimed my dick down and blasted my stockings with some cum too. I was totally wiped out by this mind shattering orgasm. I don't think I have ever cum as hard or as long as that before.

As I laid there recuperating, Toni leaned over me and licked all my come off of my clothes and skin. She then licked the last drop off of my face and stood over me. "Open up, lover." she said.

I smiled at her and opened my mouth and she spat my cum into my waiting mouth. I swallowed it down immediately.

When we all caught our breath, Eric and Toni confessed to me that they had cooked up the whole situation days ago, before Toni left town. Then Eric and I told her about our adventures at the Bookstore Theater. Toni said that turned her on, then she got a little gleam in her eye. But that's another story.

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7 Comments
AnonymousAnonymousover 1 year ago

Not exactly the same story but very much like myself I'm a married cock loving cum eating sissy who my wife caught years ago and now I have to suck fuck and be fucked by who ever she wants and I really love black dick

Larry Smith

AnonymousAnonymousalmost 10 years ago
I'm a sissy boy too

I too am a sissy boy who loves crossdressing while my boyfriend fucks me and my wife watches. She then fucks me with her big strap-on while my boyfriend feeds me his cock & shoots his big load of cum down my faggot throat. Please tell more stories like this one.

AnonymousAnonymousabout 10 years ago
great story

This story really turned me on because it's my real-life fantasy -- I truly wish my wife would catch me sucking on a big cock and then treat me like your wife treated you. I have sex often with men while I'm dressed in panties, nylons & a bra and I love sucking cock & getting fucked. However, I haven't told my wife yet. I truly wish she would react the way your wife did. I'd love to suck another man's cum out of her cunt and it would turn me on so much if she watched me suck another man's cock. Your story has inspired me to try and talk to her about it. Maybe one day she'll "accidentallly" catch me and my lover having hot gay sex. Can't wait to read your other stories -- keep up the great writing.

AnonymousAnonymousabout 12 years ago
I wish my wife was like Toni.

Your story is so hot that I came hard in my hand and licked it all up. I wish my wife would be like Toni and catch me sucking my lover's cock and then watch us while he fucks my man-pussy. I love dressing in her sexy clothes and I've even bought some panties, nylons & bras in my own size (yes, the salesgirl knew they were for me and that really turned me on because she knewI am a sissy bitch). Can't wait to read your other stories.

AnonymousAnonymousabout 12 years ago
Not for Me

The sissyboy role is not for me, but I can appreciate the writing. Not clear whether Eric was (again) Toni's brother.

Keep writing -- your stories are very creative.

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