A Sissy Surprisebynancyallen©
I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs.
I walked into the bedroom and stopped dead in my tracks. My boyfriend was on his knees facing away from the door and sucking on the cock of some guy I'd never seen before.
"Jeff? What the fuck is going on?" I demanded as I walked towards them, wondering why he was wearing my dress and where he got the black fishnet stockings and red spike heels.
He pulled away and tried to stand up as he stammered, "Oh god, I ... I'm so sorry Nan! I thought you were ... oh damn."
When he finally stood and turned around I saw the smudged bright red lipstick, blush and blue eye shadow. I thought to myself, "When did he learn to apply make-up?" That's when I noticed he was also wearing a short curly blonde hair wig.
The dress he'd chosen was one of my favorites--a black figure-hugging skimpy dress that was extremely low cut. We were about the same weight so he easily fit into it, though it was a bit more snug across his shoulders and only went to about mid-thigh on him because he was so much taller than me. I could see the outline of a bra and wondered if it, too, was mine and if he'd stuffed it or if it was his moobs filling it out.
"Who's your boyfriend?" I demanded as I crossed the room to where they stood. Jeff was shaking as I stared at him.
"Franco, a guy I know from the bar."
"Hello, Franco," I greeted and shook his hand. Franco was about the same height as Jeff but slim and muscular. He looked European and had dark tanned skin with brown eyes and shoulder-length wavy brown hair. "Have you two been lovers for very long?"
"No," Jeff answered. "This was ... is the first time."
"I see," I replied as I trailed my finger down Jeff's back and felt panties. I wondered if they were mine or if he had the decency to buy his own. "So, then, do you wear my clothes often?"
"Please Nan, don't do this in front of Franco," Jeff pleaded.
"Answer the question sissy bitch," I demanded with an angry edge to my voice. I reached for Franco's cock and wrapped my fingers around it then started to give him a hand job. "I'm sure Franco won't mind you answering a few questions about your ... habit."
Jeff blushed as he stared at my hand moving up and down Franco's cock. "Sometimes I do, when you go out without me."
"I see. Don't you think you should have asked me first?" I asked as I continued with the hand job. Franco moaned softly.
"I ... I couldn't tell you," Jeff stammered some more. "I'm so embarrassed."
"You're embarrassed? How do you think I feel?" I asked. "I come home and find my boyfriend dressed like a cheap hooker in my clothes and sucking some guy's cock. This is how I have to find out my boyfriend isn't a man but a sissy ... an ungrateful stupid bitch sissy girl who can't even have a fling without getting caught."
"Please Nan," he pleaded. I met his eyes and smiled deviously. He looked slightly fearful of what I was about to say.
"Lucky for you slut, I love sissies and crossdressing. Go back to sucking his cock while I get more comfortable. Then I am going to enjoy watching him fuck your pussy," I said as I started to undress. "Oh, and keep the dress on. I like that look on you."
Jeff looked stunned at my words. I had never talked that way before but I seemed to know just what to say. I was sure it was a bit disconcerting for him as I'd never told him I had a thing for sissies or dominating men. It really brought out the bitch in me and made me super turned on.
"I think I'll call you Jeffra. Hmm. No, that's too close to your masculine name. I know, your name will be Julie," I said. "That's a nice name for a slut like you. What do you think Franco?"
"It is a lovely name," he replied. He was smiling broadly.
"Now Julie, if you don't start sucking that cock I'll have Franco fuck me up the ass and you won't be allowed to touch your clit for a week," I said.
I finished undressing and sat on the edge of the bed while Jeff dropped to his knees. I ran one hand over my breasts as I guided Franco's hand between my legs. He slipped a finger between my lower lips and rubbed it over my clit.
Franco used his other hand to guide his nine-inch thick uncircumcised cock to Jeff's mouth. He moaned when Jeff's lips touched the tip then slid down the shaft. Jeff watched me out of the corner of his eye, following Franco's movements between my legs.
"Do you like using the slutty Julie's mouth?" I asked as I tugged and pulled on my nipples. My pussy was gushing. I hadn't had a sissy in my life for a long time and this new revelation had me soaked.
"It is most warm and wet."
"Is Julie a good cock sucker?"
"Yes Ma'am," Franco said politely. "She's very good."
"Have you been practicing Julie? Using my toys for your lessons?" I asked. Jeff nodded his head.
"Good then you should have no problem with this next order. Deep throat the cock and hold it there, Julie," I said as I caressed his nipples through the clothes with my big toe. I was happy to discover his bra wasn't stuffed.
Franco pulled almost all the way out then shoved his hips forward and pushed all of his cock down Jeff's throat and held it there for several seconds. Jeff was gasping for air when Franco pulled back.
"Did you like that Julie?" He looked confused and didn't answer. "Do it again Franco. It wasn't long enough for him to make a decision. Hold it a bit longer this time."
"Yes Ma'am," Franco said then forced Jeff to swallow his cock again.
I stood up and moved behind Jeff. I pressed his head against my stomach and held his head still. "Fuck my slut's pretty mouth," I said as I looked down at Jeff's face. His eyes met mine and I could see the look of confusion still in them.
"You're a lucky girl, Julie, to have that long thick cock using your mouth," I said. "When you've decided you like sucking cock you can tap my leg three times."
Franco played with my breasts as he continued to fuck Jeff's mouth. He tugged and squeezed the nipples hard. "Oh yea, just like that," I moaned loudly.
I felt three taps on my leg. "Make his lips touch the base of your cock," I said. "Then I'll get the lube so you can fuck her pussy."
Franco obliged, shoving his cock all the way in, as I stepped back. I picked up the anal lube from the bedside table. "Julie, bend over the side of the bed and pull that dress up like a good slut so we can see your pussy."
Jeff stood up and moved into position as I covered Franco's cock with the lube. "Julie is an anal slut. She loves to have her ass filled with my toy cocks, so no need to be gentle with her. Isn't that right, Julie?"
"Yes," he answered. I could hear the embarrassment in his voice.
I pulled the white panties Julie was wearing, thankful they weren't a pair of mine, down to his knees then cupped his balls and cock. "Her clit is rock hard. I think she likes being called a sissy slut," I said as I lightly squeezed them.
I spread the lube around Jeff's ass hole then dipped my finger inside. His tight ass gripped my finger and sucked it in deeper. Jeff moaned softly as I pushed the finger in further.
"Such a slut," I said as I slid my finger completely into his ass and rubbed against his prostate gland causing him to moan. I winked at Franco then pulled my finger out guickly. Jeff gasped then groaned at the feeling of emptiness. "Don't worry slut, something much bigger is headed your way."
Franco moved into position and I stood next to him. I spread Jeff's ass and revealed the rose bud hidden between the fleshy cheeks. I could feel my juices dripping down my thighs as Franco filled Jeff's ass with his cock. My number one fantasy was coming true and I was giddy with anticipation.
"He's too big!" Jeff cried out as the thick cock slowly pushed into him.
"You can handle it, my anal slut. Remember what that call girl taught you," I replied as I massaged his ass cheek. "Take it all in so he can fuck you then you can fuck me."
Jeff replied with a groan but did it. A strong thrust from Franco finished the job and his cock was fully encased in Jeff's ass. He started to fuck the tight hole slowly.
"How does his pussy feel?"
"So very tight," Franco answered as he continued to move in and out. The huge smile on his face left no doubt as to whether or not he was enjoying it.
"Julie, you should see him fucking you. It is so hot," I said as I reached under him to caress his cock. "Oh my, your clit is so hard and you're so wet. My hand feels like it is gliding over water."
With my other hand I squeezed and teased Franco's nipples. He moaned his appreciation as he started to fuck Jeff faster.
I was in heaven but didn't want to be left out of the fun. "Roll Julie over so I can ride her."
Franco pulled out so Jeff could roll onto his back. He put Jeff's ankles on his shoulders then slid his cock back into his ass with ease. I straddled Jeff's hips while he held his cock in position so I could slide my pussy onto it.
"Oh yeah," Jeff and I moaned together. His cock inside me was just what I needed. Franco reached around me and cupped my huge breasts as he continued to fuck Jeff's ass, using my breasts as handles. Jeff watched me bounce up and down on his cock, his hands resting on my hips to help control my motions.
"Julie, you're so sexy in that dress," I cooed. "I can't wait to get you into some of my other clothes. And buy you some lingerie so you look pretty when I fuck your ass or when we have company like Franco."
"Oh god Nan," Jeff gasped. "I'm going to come!"
"Come before me and Franco will come in my ass then you will eat my ass and lick up all his cum," I threatened. Jeff closed his eyes as he tried to think about anything but orgasming. I reached out and started playing with Jeff's moobs. I found the nipples and tugged on them.
"Oh...fuck!" Jeff cried out as he filled my pussy with several strong bursts of cum.
Franco pulled out just as Jeff started to come so he didn't accidentally come too. I let Jeff finish then laid across his chest. "Naughty girl! But I don't mind Franco filling my ass with the cum that should have been yours."
Jeff helplessly watched my face as Franco spread my cheeks then slid his cock into my ass with ease. "Oh god, he's so fucking big. No wonder you came so hard so fast. Too bad your clit is all floppy and soft now. Franco is left on his own to do the job."
"Nan!" Jeff exclaimed as his face turned a bright red.
"Hush girl or I will make you wear that dress for the rest of the weekend," I said then moaned as Franco drove his cock fully into my ass. He started moving faster, his balls slapping against me.
Jeff tried to kiss me as I got reamed on top of him. I turned my head away and frowned at him. "You were a bad girl, no kisses for you."
He pouted but stopped trying to kiss me. I smiled down at him as I ground my huge breasts against his moobs. I could feel his cock getting hard again from the friction of my pussy lips pressed against it. I reached between us and pressed the cock between the lips so my clit would rub over it as Franco fucked me harder and faster.
"Oh god Nan," Franco gasped as I tightened my ass around his cock. "I'm going to come if you keep doing that."
"Not yet ... I'm almost there," I replied and leaned down to whisper in Jeff's ear. "Bite my neck and make me come."
Jeff smiled as he turned his head towards my neck. He licked and kissed my neck, then started to lightly suck on it. I whimpered my appreciation. Franco was now slamming his cock in and out of my ass. I was in overload. "Bite me now you fucking slut," I demanded. Jeff opened his mouth wide then bit down on my neck.
"Oh fuck!" I cried out as my body exploded. My ass muscles tightened around Franco's cock and he slammed into my ass one last time to dump his load. He pulled out at the end to leave two pools of cum on my ass for Jeff to clean up.
I carefully slid off Jeff with Franco's help and laid on the bed. "Clean me naughty girl," I ordered. Jeff sat up and moved behind me. "Clean all the cum up. If you miss a spot Franco will let me know."
Jeff swallowed then started to lick up the pools of Franco's cum and blanched. I moaned as his tongue moved across my skin. I gasped as his tongue moved down my crack to my ass hole. Franco spread the cheeks so Jeff could really get in deep.
"Don't stop until I come!" I ordered. Jeff continued to lick my ass as his fingers slipped into my pussy. He finger fucked me with two fingers and found my G-spot. I ground my ass against his mouth. I had been on the edge and it didn't take me long to get off. "Oh fuck! Yes! More ... oh god!"
When I finished coming Jeff sat back on his heels as I slid off the bed and stood before the two men. "Go hit the shower, there are clean towels in there," I told Franco. He smiled and nodded his head then slipped into the master bedroom. I looked down at Jeff.
"It seems we have a new order in the house, don't we Julie?" I asked as I caressed his cheek. "I hope you like your new girly name. I think it suits you well. Don't you agree?"
"Yes, I like it," he answered.
"You seem to have forgotten something," I said. He looked confused. "You will address me as Ma'am as long as you're in drag. Do you understand?"
"Yes Ma'am," he answered.
"Stand up, Julie. It is your turn to shower. Don't forget to brush your teeth and use mouthwash. You can come back as Jeff so we can give Franco a proper send off."
Franco came back in with a towel wrapped around his hips. Jeff stood up and headed into the bathroom. When the water started, I turned to Franco. "Thank you for using my slutty girl. She has much to learn. Would you like to help me teach her how to be a good cock sucker and well behaved girl?"
"Yes Ma'am, it would be my pleasure," he answered.
"Excellent! I am looking forward to it," I replied and kissed him softly as I ran my hand over his cock. It started to grow. "I want you to be fucking my pussy when Julie returns. Would you like that?"
Franco smiled and dropped the towel, exposing his now hard cock. He pushed me back on the bed and spread my legs. I smiled as he paused with his cock at the entrance then he shoved as much of his cock into my pussy as he could in one go.
I guided his hands to my breasts and he squeezed them several times before letting his fingers slide along the skin to the nipples. He rubbed them between his fingers then tugged on them. I moaned softly as I lifted my hips to meet his thrusts.
"Franco, you're a very good fuck," I said as I saw Jeff coming out of the bathroom. He stopped in the doorway and stared. "It is so nice to be fucked by a real man."
"A beautiful voluptuous woman like you deserves a real man to fuck you. Not just some sissy," Franco replied as he filled me with all of his cock and hit the back wall. I pretended not to notice Jeff standing in the doorway.
"Fuck me hard Franco ... make me feel like a woman," I said as I glanced over at Jeff. His face was bright red with embarrassment. "Oh god! Yes, Franco. Just like that!"
Franco fucked me harder and faster as he tormented my nipples. I tightened my pussy around his cock and massaged it from the inside. He moaned loudly. "Oh, I like that," he moaned. "Do that again."
I obliged then reached between my legs to find my clit. It was swollen and sensitive to my touch as my copious juices leaked out of my pussy. Suddenly Franco slid his hands under my ass and lifted me off the bed so he could get in even deeper.
"Franco ... oh god ... oh, I'm going to come," I cried out. He swatted my ass as he continued to fuck me.
"That's it ... come for me baby," he urged, returning one hand to my breasts while the other continued to hold my hips up.. "When you come I'm going to fill you to overflowing with my cum."
"I ... oh Franco ... I'm coming!" I cried as my pussy exploded around his cock. He threw his head back and started fucking me with short fast strokes.
"Here it comes," he said then started to come. I could feel stream after stream of his cum shoot deep inside me. Franco left his cock inside me to feel the last twinges of my orgasm.
"Thank you Franco," I said then blew him a kiss. I turned and acknowledged Jeff. "Oh good! You're done! Get dressed then we'll walk Franco out. Oh, and Julie, Franco has agreed to help me teach you to be a good cock sucker and train you."
"Great, I can't wait," Jeff said as he got out clothes to wear then got dressed. Franco quickly pulled on his gym shorts and t-shirt. I put on my robe then we headed downstairs.
"Give Franco a kiss," I told Jeff. He glared at me but kissed Franco at the door. I kissed Franco too then we watched him head down the walkway to his car.
"Nan ... I saw you fucking Franco," Jeff said.
"I know; I wanted you to. You are my sissy girl now and I need a real man to fuck me. I need to you understand that I'm only allowing it because you need to know who the sissy is and who the man is. Don't worry baby," I said as I wrapped my arms around his neck and pulled him down for a kiss. "I'm still going to let you fuck me as much as always."
Jeff smiled a little in response. I kissed him deeply. "You have made me very happy today. I've been wanting to see you dressed up but I didn't think you'd go for it. A few of my all time favorite fantasies were fulfilled today. Thank you so much. I love you."
"I love you, too ... Ma'am."
We walked into the living room and snuggled on the couch in front of the TV, both very happy with the outcome of today's adventure.