Crossing the Line

[Scout]

[Note: This story was inspired by an erotic cartoon]

“Almost ready,” my wife whispered in my ear, as she led me from our bathroom into our bedroom. “Keep your eyes closed.”

“Wait,” I said. “Do I hear someone?”

“Trust me, Andy,” she replied. “I have a wonderful surprise for you.”

***

It had started earlier in the evening as a game. Or so I thought.

My wife had told me she wanted to dress me as a woman. Well, not just dress me – she used the word “transform” me. I thought it might be fun. A couple of weeks ago, after a few too many drinks, I had confessed to her that I had an inner feminine side and often fantasized about have sex with a man. Since then she had been teasing me about it and urging me to express my femininity. I have to admit it turned me on when she coached me to make womanly hand gestures or walk with a wiggle. Then tonight she announced it was time to try the next step.

It started in the shower, where she helped me shave my body hair, including my armpits. Then she sat me in a chair to cut my hair. She likes to style her girlfriends’ hair so soon I had a pixie cut with ringlets on the side, all very cute and girlie. Of course, I had a raging hard-on the entire time, and since I was naked she could see it. Next she told me to dress sexy like I would if I were going to bed with a guy. She gave me a clingy black camisole top, a black thong, and black thigh high stockings. Finally, she produced a set of high-heeled black pumps. “I bought these for you, honey,” she had said with a big smile. They fit me perfectly.

“Now for the finishing touches,” she declared. “Nails and make-up.” She had told me not to cut my fingernails for the past two weeks. She filed them into a rounded shape and painted them with her most trampy deep-red polish. At her direction, I had shaved closely just before we showered. As I sat on her make-up stool, she did my face, with base and shading, eye liner and mascara, and then red lipstick.

“Wow!” she exclaimed when she was done. “You’re really quite pretty. Take a look.” I stared at myself in the mirror. I was amazed at how different I looked. I was utterly feminine and surprisingly cute. It felt wonderful but also kinda weird. My wife admired what she had done to me, “If we went out to a bar, honey, men would be hitting on you. I’m actually jealous of how sexy you look.”

“You need some pretty jewelry, too.” She took off her wristwatch and told me to put it on. I admired the thin black leather band and small round face – it was unmistakably effeminate. Then she slipped off her diamond solitaire engagement ring and slid it onto my ring finger. Our hands are almost the same size and it fit me perfectly. I felt so sexy!

At some point my wife had closed the bathroom door. She instructed me to come with her into the bedroom, walking so my hips would wiggle just as we had practiced. Then she took my hand and told me to shut my eyes tight as we went into the bedroom. I heard the bed creak.

***

“Kneel here by the bed,” my wife said.

“I’m getting nervous,” I said. “Who is it? One of your girlfriends?”

“Um, not quite. You can open your eyes now.”

I gasped: sitting naked at the edge of the bed was a very handsome, incredibly well-built man, with a rope tatoo on his right arm. “Andy, meet Kyle from my office. You told me you’d like to try it with a guy.” She had often spoken about him as her gay office boyfriend. I blushed red with embarrassment but didn’t move.

“A pleasure, Andy. Your wife’s been talking to me a lot about you lately.” 

My wife giggled. “You’re not angry with me, sweetie, are you?”

Instead of speaking, I reached out for Kyle’s dick, which was already erect. I could see pre-cum glistening on the tip. I brought it to my lips and then swirled my tongue around it. Kyle moaned, I then opened my mouth and began to suck it as I pumped it with my hand. From the corner of my eye, I saw my wife’s pretty watch and the sparkle from her ring on my finger. I felt like such a cock teaser and loved Kyle’s reaction.

“My, someone is very eager,” my wife chirped happily. “God, it’s so hot looking at you going down on him. You’re a natural at this.”

It didn’t take long. Kyle was soon thrusting deeper into my mouth, hitting my throat. I gagged a couple of times but refused to quit. As his moans and grunts got louder, I knew he was close. I pumped his cock harder and suddenly he erupted into my throat. The taste was strange but I couldn’t seem to get enough. I tried to swallow it all, but some of his warm cum dribbled from my mouth.

My wife leaned in close. “I guess you liked my little surprise, huh?”

I didn’t speak. I grabbed her face and thrust my tongue into her mouth. She doesn’t like the taste of cum but I guess she was so into the scene she responded with a passionate tongue kiss.

“I suppose I should be angry,” I said, “but I’m too horny to complain. Kyle, are you ready to go again? I need to be fucked.”

“Not yet, Andy.”

“Well, I can help,“ I replied, as I gently pushed him onto his back, my mouth poised again above his now-flaccid tool. I turned to my wife. “Honey, I want you to lube my ass. Use your tongue.”

She chuckled. “Whatever you say, sweetie.” She joined us on the bed, kneeling behind me and spreading my ass cheeks. I felt her warm breath on my virgin hole and then her tongue started to work around it. It made me quiver.

I placed my hands on Kyle’s thighs and again noticed how pretty they were with my red nail polish and my wife’s jewelry. I started to lick his dick and balls very gently, sometimes moving up to suck and nibble on his tits, which I discovered were very sensitive. In just a few minutes I was rewarded as his penis stiffened and stood tall. My own cock, not nearly as big, was hard as a rock, poking out from my black thong.

“Good to go,” Kyle said with a big smile.

I straddled his waist and lowered myself onto his thick cock. I winced at first when he hit my sphincter but I didn’t hesitate. After all, a woman has to be able to take her man without complaint! That’s what I wanted to be – Kyle’s bitch, my ass a cunt for him to use as he pleased.

I felt myself open to him, and then an amazing warmth and fullness spread from my ass to my entire body. So this is what it feels like to be fucked! I had never experienced anything so wonderful. It was much, much better than when I was inside my wife.

Soon I felt Kyle deep, deep inside me, as my ass resting on his pelvis. I had taken all of him. I whispered in his ear, “Kyle, I think I’m gay.” I didn't want my wife to hear -- I wasn't ready. He responded by pulling my face to his and kissing me deeply. My first kiss with a guy, and I knew at once it wouldn’t be the last. "Oh, yes," I heard my wife say.

Then I began to move my hips up and down, pulling most of the way off his cock and then settling on it. I did it slowly at first, then I sped up the pace. With each in-and-out movement, I felt an electric shock that started in my ass and spread outward. My wife came close to my ass, staring. “Ride him, Andy. Yes. Just like that. Ride his big cock. God, this is amazing. He is drilling your ass. It’s so sexy.”

But Kyle wasn’t able to get the leverage he needed to finish. Suddenly I felt his strong hands grip my waist and pull me off him. “Turn around, baby,” he ordered. “On your belly. Ass up, face down,” In moments he was behind me. He pushed his dick back into my gaping hole, meeting no resistance. I grunted at being taken so forcefully. Now he was in charge, setting the pace.

“Fuck me, Kyle,” I said softly. Then, louder, “Fuck my ass. Fuck my boy pussy. FUCK ME HARD!” His weight pressed me down onto the mattress. His thrusts were long and deep, and his balls slapped my ass with each inward plunge. “Cum inside me!” I begged.

My wife came around the bed, placed her hands on either side of my face, and looked into my eyes for a moment. I was in a world of pleasure beyond anything I had ever imagined. She kissed me passionately, and I think we both knew it was the last time.

And then I felt it, an orgasm that began somewhere in my ass and spread thru my entire body. “Oh, my husband is having an actual sissygasm!” My wife was beside herself with what she had done to me.

Only seconds later, I heard the satisfying sound – the deep, manly grunts – of a man cumming as Kyle reached his climax. There was one final momentary pause and then a series of pounding thrusts into my boy pussy. He collapsed on top of me. I turned my head to the side and we exchanged a deep kiss, our tongues dancing. “God, that was fantastic,” Kyle murmured into my ear.

There was complete silence in the room. Slowly Kyle softened and finally slipped out of me. I felt empty and very wet inside, and then the odd but delightful sensation as his cum start to dribbled out of me, though I clenched my hole to keep as much inside me as possible. He held me in his strong arms. I never wanted him to let go.

Finally my wife spoke. “You two looked so good together. So natural. Andy, I know that Kyle is single. You’re my husband, but I really you should be his boyfriend. What do you say?”

I paused. I knew she was right. Our marriage was over at that moment.

“Yes.”

 

 

 

 

 

[PozBottomACNJ]

Oh, if only my wife was that understanding!

[austin_submale]

Fuck...  i don't know how i missed this one before...  Super hot!