tagTranssexuals & CrossdressersGo Fuck Your Stepmother

Go Fuck Your Stepmother

byStephanieSeymour©

My stepmother said nothing for a long time as she pulled out the kitchen chair and sat across the table from me. I looked up my Algebra 101 homework. Ann had surprised me. We usually didn't talk much, especially when my father wasn't around.

The house was silent as Ann gazed longingly at me with her deep brown eyes. Then she hit me with her killer smile. The sides of her eyes crinkled into crow's feet. At 40, Ann was still a knockout, an ex-model who refused to give up on her body. Her daily workouts helped. So did the botox treatments, silicone tits and the peroxide in her hair. The whole package reminded me of a washed-up porn star.

But what time took in looks paid double in experience. Ann oozed with carnal knowledge. A stiffy formed in my jeans as I pictured Ann on her back, moaning with a sweating, grunting man on top of her. I immediately felt ashamed and shifted uncomfortably.

But Ann was just getting started. She slowly leaned forward and set her elbows on the table. Part of her silky, red robe fell away from her body, exposing one perfectly round breasts. I tried not to look, but the eyes had other plans. Everything but the nipple was exposed.

Ann reached across the table and put her hand on mine. I felt the hairs on my arm stand up.

"Honey," Ann said. "I'm wondering if you could take a break and come up to the bedroom and help me out."

My mind went blank. I tried to speak, but nothing came out. I could barely breathe. I sat there, frozen. It was like my darkest fantasy was coming true. Fucking my stepmother? Could it be happening? No way, I told myself.

Ann reassuringly squeezed my hand.

"I know you've got mid-terms coming up," she said. "And I know how important they are. I was once in college, too, you know. So, if you're just too busy, I'll understand."

Adrenalin surged through my body as I saw the opportunity flash by.

"No," I said, as my voice cracked awkwardly. "I need a break. I'd love to help."

Ann flirtatiously tipped her head and smiled.

"Great," she said. "Follow me."

Ann led me by the hand down the hall. When we got to the stairs, she had to let go to climb up. She went up two steps and turned around to look down at me over her shoulder.

"Stay close," she said. "I wouldn' t want to lose you."

"Uh, sure," I said.

I didn't understand. We'd lived in the same house together for four years. I knew perfectly well where her bedroom was. But I smiled nervously and nodded as Ann tossed me a wink and stepped up.

Her hips swayed as she slowly ascended the steps. I stayed close, just as she'd asked. It was impossible to not watch her perfect, apple-bottom ass swishing from side-to-side under her robe. She was about five steps from the top when the robe flipped up just enough for me to see Ann wasn't wearing any underwear. No thong, nothing.

That was when I really began to wonder what was going on. First, Ann flashed me her tit at the kitchen table. Then she showed me her bare ass. All this when my dad was out of town on a business trip. I began to take seriously the thought that my own stepmother was trying to seduce me. But I forced the idea out of my head. This was my father's wife, after all.

We rounded the corner into the bedroom Ann shared with my father. A black bra and matching panties were laid out next to a red dress on the white bedspread.

"I know this is going to sound really weird," Ann said. "But I'd like you to put this on."

"Really?" I asked. "Why?"

"This is the outfit I'm wearing to your cousin's wedding next month," Ann said. "I need to find the exact right accessories to go with it."

"Can't you just try it on yourself?" I asked.

Ann bit her lip and thought for a second.

"I suppose I could," she said. "But it makes a world of difference to see it on someone else."

I looked at the dress, then up at Ann. She was blinking at me with puppy-dog eyes. Irresistible.

"Oh, all right," I said.

"Thank you!" she said.

Ann gave me a little golf clap, as I stripped off my T shirt. When my head came out the other side of my shirt, I expected to see Ann vacating the room. But she was taking a seat on the bed.

"Aren't you going to step out?" I asked.

Ann shrugged.

"We're family," she said. "What's the difference?"

There was a big difference, but I wasn't going to argue. I flung my shirt into the corner and then pulled off my jeans and boxers at the same time. My boner popped up and pointed straight at Ann.

"Ooh," she said. "It looks like somebody's happy."

I smiled and felt the warm rush of my face turning red.

The bra went on first, but it wasn't easy. My simian fingers couldn't hook the two metal hooks behind my back. I kept letting go of one end. Ann watched at the elastic strap whipped around my body.

"Come here," she said.

I backed up to her and let her fasten the hooks before sliding the shoulder straps up my arms.

"Let me have a look at you," Ann said.

I turned around.

"Aren't you just looking so sexy?" she said.

With the bra strap digging into my flesh, I sure was feeling sexy. It surprised me. I had always been curious about cross-dressing but never had the guts to try it. So far, I was totally digging it.

I slid the panties on next. They were boyshorts with plenty of room up front for my balls. The backside slid up my ass, giving me an automatic wedgie. I adjusted my cock so that it was pointing up at my belly-button. Every time I moved, the sensitive underside of my prick rubbed against the lace. I had to concentrate to keep from cumming in the panties.

"Now the dress," Ann said.

I pulled it over my head. The stretchy material hugged my body from my thighs to my shoulders. The scoop front covered the bra straps but left plenty of chest exposed, while the bottom exposed lots of leg.

"Perfect," Ann said.

She picked up the phone on the nightstand and punched in a number. She held the receiver up to her ear and paused for a second. Then she said, "Hi, it's me. Spiderwoman just caught a fly...Yeah, it's the one we talked about. Come on up."

Ann hung up and smiled at me sideways with an arched eyebrow.

"What's going on?" I asked.

"Juan the landscaper was waiting in his car outside," Ann said. "He's coming up."

"He's coming up here? Now?" I asked. "I've got to get out of these clothes."

"Not so fast, baby," Ann said. "We're all gonna have a little fun."

The front door slammed shut and then Juan thumped up the stairs fast and hard. I just stood there, feeling foolish and staring numbly at Ann's smiling face.

I hardly recognized Juan when he lumbered through the door. I was used to seeing him in a raggedy T-shirt and jeans, all covered in dirt, but he had cleaned himself up. Juan had his black hair slicked back. His muscular arms strained against the sleeves of his shirt. Juan's neck barely fit through the collar.

Juan rushed at Ann. He wrapped her in his arms and gave her a long, slow, deep kiss. His hands reached under her dress and between her legs. Ann purred as Juan rubbed her pussy over her panties. Juan broke off the kiss and smirked at me.

"You like watching a man touch your stepmother's pussy?" he asked, while still holding her in his arms. "Maybe you want to watch me fuck her."

I was utterly stunned. If Juan were at all surprised that I was dressed in woman's clothing, he didn't show it. I said nothing.

"You don't know what to say, eh?" Juan said. "Ees OK. I not here to fuck her. I here to fuck you."

I gulped.

"What?" I asked. "You said f-f-f-fuck me?"

Ann gently pushed Juan away.

"Oh yes," she said.

Ann wrapped her arms around me and slipped her tongue into my mouth. I smelled Juan's cologne on her as my hard cock pressed into her pubic bone. Our tongues played sword-fight until Ann withdrew and kissed her way across my cheek. She breathed heavily into my ear.

"Juan is going to fuck your ass," she whispered.

Ann dropped to her knees. She pushed the bottom of the dress up to my waist and yanked down my panties. With my bare ass exposed, Ann stood up. Her gaze burrowed deep into me. Something in her changed. In a few seconds, her face went from understanding and caring to harsh and punishing. The last thing I saw before she slapped me across the cheek was her furrowed brow.

"Get into position, you fucking bitch," she said.

I got into the doggy-style position on the bed. Ann let her robe drop to the floor. She went to a nightstand and pulled out a shiny, gold dildo. Ann got on the bed in front of me with her back against the headboard and her legs spread. The dildo stood at the ready in her right hand, as her slit glistened.

The mattress shook as Juan knelt on the bed behind me.

"Spread your cheeks, beetch," he said.

My face fell onto the soft comforter as I reached back to hook my fingers into my butt cheeks.

"Mmmm, yeeees," Juan said. "Dees ees what I like to see. A nice, virgin brown eye. But you ain't gonna be a virgin much longer."

Juan squirted some lube onto two of his fingers and gently inserted them into my love hole. I couldn't see what he was doing, but he must not have gone further than the first knuckle. There was no pain. He applied just enough pressure to let me know he was preparing me for something bigger. Much bigger. My ass muscle began to loosen.

"I like dees one," Juan said. "Nice and clean."

Ann smiled and nodded.

"Enjoy her," she said. "It's tough to find virgins."

She turned a dial on the bottom of the dildo. It vibrated to life. She set the tip onto her clit. Her head rocked back with pleasure.

Juan squeezed my hips and began to poke my bung hole with his cock, as if he were knocking at a door. My prick felt ready to burst, even though no one had touched it. I curled my palms into fists and imagined what it would be like to have another man up inside me.

Juan gave my door three final knocks and then blasted his way in fast and hard. It was a shock to the system, like diving into a cold lake. I heard myself grunt. I could hardly believe it was happening. Never did I imagine that I'd have a cock up my ass.

After the first shot, Juan fucked me slowly and gently. He gave me just a little more meat every time his hips rocked forward. If sex were dancing, he and I would've been doing the waltz. The shock began to wear off and slowly turned to pleasure. I began to moan. Juan was into it.

"Awwwww, yeah," he said. "So tight, so tight."

Ann was digging the show. I couldn't see her because my face was dug in the comforter, but I could hear her working the vibrator hard.

"Ooh," she cooed. "Ooh. Ooh. Ooh."

Juan began to pick up the pace. Our waltz became a tango. I soon felt something gently rapping against my ball sack. I searched my mind for what it could be. Then it hit me. It was Juan's ball sack. That's when I knew he was thrusting all of himself inside me.

Juan had been holding back, and I could tell he was having a tough time. He wanted to ravage my virgin he-cunt. But he needed a signal from me, something that said it was OK for him to unleash beast. I tried to speak. My throat was dry. Nothing came out.

"Give it to me, baby," Juan whispered. "Give it to me."

I summoned all my energy to my vocal chords.

"Fuck me," I gasped.

Juan didn't wast another second. He slammed his cock into me, backed it up and did it again.

And again. And again.

Our dance quickly turned into a mosh pit. Juan showed no mercy. With each thrust, he poked something deep inside me that I didn't know existed. I reached a plane of anal ecstasy I never thought possible.

But just when I thought he was going to cum, Juan pulled out. Ann instinctively tilted back her head and opened her mouth. Juan stood on the bed and walked over to her, struggling to keep his balance on the soft mattress.

When he got within range, Juan aimed his cock, stroked it twice and shot an enormous wad across Ann's cheek. The next burst landed on her tongue. He kept going until his balls were empty. Ann's face was gooier that a freshly baked cinnamon bun by the time Juan finished.

Juan shook the last drop from his cock onto Ann and then turned to look at me.

"She ees ready for you," he said.

"Huh?" I asked. "Whadda ya mean?"

"Go fuck your stepmother!" he yelled.

Ann slid down so that she came to lie flat on the bed with her legs spread. I positioned myself between her thighs with my hands planted in the mattress next to her shoulders. She smiled up at me with her cum-covered lips.

"Pump my cunt," she said, spraying jizz at me.

I dropped my face toward hers and thrust my hips forward. My cock and tongue entered her at the same time. I tasted Juan's salty goo, just as Ann's warm flesh swallowed my swallowed my prick. Ann grunted. I took slow, gentle strokes inside her while licking Juan's cum off her face. I cleaned the left cheek, then the right. Her pussy felt like silk. I shoved myself all the way inside her with every stroke. Ann moaned appreciatively.

I was probably fewer than 20 pumps in when I shot my own load deep inside her. Ann shuddered. She inhaled deeply. The jizz shot for a long time. I must've dumped a pint of goo in her.

After squeezing out the last drop, I rolled off Ann and stripped the dress and bra. Juan flopped onto the bed next to Ann and stretched out as I put on my T shirt and jeans. I wasn't sure what to say on the way out of the room. There is no traditional farewell for this sort of situation.

Juan broke the silence.

"So, you like dees?" he asked.

"What do you mean?" I asked.

"Dees, you know, I fuck you. You fuck your stepmother? You like?" he asked.

I looked at Ann. She nodded.

"It's OK," she said. "You can be honest."

"Honestly..." I said.

Juan and Ann waited for me to finish with their eyebrows arched and smiles spreading across their faces.

"I loved it," I said.

"Good," Juan said. "Maybe next time we get your stepsister to watch."

I nodded and then went downstairs to finish my homework.

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