Femboy Sex Stories

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“Promise me you won’t laugh…”
That’s what I said. This was so strange for me. I hadn’t ever done anything like this before. I peeked out of the bathroom door of the fancy hotel we had checked into. It had been a really amazing day. We went to a movie, he took me out, he held my hand and made me feel wanted… But this was still so strange and new. I stood there with my make up I had painstakingly applied, my wig fixed perfectly on my head, a cute long sleeve shirt with short shorts, and a pair of thigh high stockings… Dressed like a girl, for the first time. I stepped out and he looked at me, his eyes intantly lighting up.
“You look amazing… why would I laugh?”
I shifted uncomfortably, the blood flushing in my cheeks.
“You promise?” I asked, looking up at him.
His grin was enough reassurance. He wrapped his arms around me and held me close to him. I felt warm, I felt safe.
“Promise.” He said.
His curly hair and slender features were charming to say the least, and even though he wasn’t the most striking physical specimen, his arms felt so strong and inviting around me. I looked up at him and he leaned in for a gentle, soft kiss. I had kissed him the night before, but dressed like this, in this moment, it felt different… I opened my mouth a little, inviting him with a quaint little moan. He kissed me lightly, lips dancing over each other, tongues playing with one another, smiles creeping over each of our lips.
“I can’t believe you did all this for me…” he said, rubbing down my back slowly. I had always had curves that would fit a woman, and his hands moved to my hips, smiling down at me.
“O-of course…” I said shyly “You flew 3000 miles just to see me, the least I could do was dress up for you…”
He had flown from Oregon to stay the weekend to see me… and I couldn’t have been happier. Our first night together was one of… experimentation, to say the least. I’m not the kind of girl that does “that” on the first date, but with him I made that exception. By “that” I mean going down on him, not… that other thing. I hadn’t done that yet… but I had a little plan in the back of my mind to make that happen sometime this weekend.
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A little moment of soft embrace.
“So… what do you want to do?” He smiled down at me.
“I um… I have no idea.” I giggled.
“Let’s watch something and snuggle up, yeah?” He rubbed my hips.
“Sure~” I mused as he took my hand and led me to the bed.
It was a big, soft, king sized bed. The hotel we were at was very, very nice. The room was huge, and even though he wasn’t a rich man, I could tell he spent quite a bit on it. I climbed into the sheets and smiled over at him, crawling in beside me.
Hours must have passed with us watching Youtube videos and laughing, holding hands, his arm around me and my head on his chest… We talked about all the times we’d spoken before online, all the times we’d been “intimate” in that way, but… it was nothing compared to the swirling, warm feelings I felt spreading from my stomach every time he would lightly caress my arm with his fingertips… I was already dying for him, but I couldn’t tell him that. I had to play it cool, and hide my shaking, nervous demeanor as well as possible.
He kissed me again. But this time it was a different kind of kiss. He kissed me with a hidden lust I could almost feel pouring from his lips into mine.
I felt something… I can’t quite place it, but it was there… deep, deep down in my most sensitive reaches as his lips moved to my neck softly, a grin creeping across them… I felt my hips move without me meaning them to, and my nipples perk… He was really good at that. He shifted and moved more on top of me, holding my hand a little tighter as his kisses worked their way back up to my soft lips… His tongue lapped at my upper lip and my mouth opened with a quiet, shaky moan. I felt chills move down my form, and this swirling mix of lust and other emotions I can’t place building in my mind.
“You’re so damn sexy…” He whispered as he kissed me slowly and sensually…
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He was so gentle and patient with me. I loved that about him. I felt his fingers run their way up my shirt and I gasped softly as I felt his fingertips find their way to my nipple. He began to rub it agonizingly slow, it almost aching from the sensation he was giving me. I felt my hips buck a little and my little buddy down there begin to grow and throb. He knew what he was doing to me, how much I wanted it…
“Mhh… thank you… I-I try?” I whispered back, half moaning.
He licked my lips softly. “You succeed, lil’ lady…”
I grinned at that. Being called a lady just made me feel more turned on.
He climbed all the way on top of me and I wrapped my legs around him. I could feel him kissing my lips, then moving to my neck, my hips winding with lust, our respective bulges rubbing against each other. Mine was straining against my panties at this point, and I’m pretty sure there was a little wet spot even visible through my shorts.
as he worked his way down my form, my soft, frail feminine frame winded underneath him, his lips dancing down it with grace and intent. He lifted up my shirt slowly and kissed up my abdomen, causing another round of chills to run up me. I inhaled shakily and gripped his hand tighter.
“Oh.. I think she likes it~” He said coyly, biting his lip.
I did. Oh god yes I did.
I nodded “Mhm…” and his lips found their way to my nipple as his hand slid into my shorts. I moaned for him cutely. My voice was always high, and I had gotten pretty good at my female voice and moaning through practice, so he responded by gripping me down there and moving his hand up and down as his lips and tongue wreaked havoc on my sensitive, budding breasts. I squeezed his hand and allowed him to ravage me like this. The feeling, the sensation, it all felt so perfect. Like it was always supposed to. I found my own free hand moving on its own down his chest to feel for his own stiff, growing erection hidden away in his jeans. I unbuttoned his button and felt him smile around my nipple.
“Hm… I wonder what you’re after?” He flirted.
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I just grinned with my eyes closed and bit my lip as my I unzipped his pants too.
“Something~” I said coyly through my panting.
I worked my way into his boxers and found what I was after. It was thick but not too long. Just long enough, I would say. I had had some experience with it the night before, so I wasn’t surprised to find it was already dripping with pre and hot and warm. I leaned up a little and attempted to slowly stroke him up and down to the best of my ability considering the angle I was at.
“Mh… god yes…” I whimpered.
He grinned and leaned up, looking down at me as I worked him with my soft hands.
“You want it…?” He bit his lip.
“Only a lot…” I groaned.
He climbed out from between my legs slowly and laid over on his back. I looked over at him and took the cue that this was my moment.
“Come and get it.” He put his hands behind his head and looked over at me.
I almost giggled as I climbed over on top of him and slid down his legs, straddling him. My erection was straining hard against my panties and shorts, and I was struck with a primal hunger for what was inside of his.
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I leaned over and brushed my wig behind my ear delicately, eyeing him while biting my lip.
I pulled down the front of his boxer briefs and almost jumped when it sprung free, finally free from its denim and cotton prison, throbbing and standing tall. I looked at it with probably the same intensity a boa looks at her prey before it strikes. Hunger. I gripped it and looked up at him with my deep blue eyes locking onto his brown and green ones. I stroked him slowly a few times, savoring the warmth and girth of the member he’d been blessed with.
“Ah… yeah..” He groaned as I opend my mouth and stuck my tongue out.
I wrapped my lips around it and pushed it into my practically drooling maw. I savored his taste. Salty, sweet, and tangy. I could taste his pre on my tongue as I began to work him and suck good and hard for this generous, charming man. He moaned in response and moved his hips ever so slightly. He was holding back. I knew the way I was sucking and stroking him so slowly he must have wanted to grab my hair and shove it in, but didn’t. I loved that about him. Such a gentleman. I rubbed my hands up his abdomen to his chest and moved my head up and down. Considering the night before was my first experience doing this, I believe I was doing really well. I knew not to let my teeth hit it, and I knew to suck hard as you got closer to the tip. Having one of my own, I knew what felt good and what didn’t. Being the way I was did have its advantages. I looked up at him, his face twisting into a look of total pleasure that turned me on and only increased my intensity and lust as I worked him. I popped him out of my lips and licked him all the way up. I was loving this. He was all mine. There is a sense of satisfaction and happiness you get from feeling that you’re causing someone so much pleasure with so little effort. I kept it up for a few minutes, his breaths becoming quicker and my own erection practically screaming at me to pay attention to it.
“Oh my god you’re… you’re really good at t-this…” He panted.
I pushed it as far as I could into my throat.
He tensed and groaned loudly.
I loved it.
As I withdrew it I took a breath of air and couldn’t hold back anymore. I unbuttoned my own shorts and pulled down the front of my panties, freeing my own stiff, throbbing heat. It was a little longer, and bigger around than his, but considering I look like a woman, I don’t think it bothered him much. I slid up on him slowly.
“I’ve always wanted to try this…” I grinned.
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I pressed my length against the underside of his, straddling him with one hand rubbing his chest.
I started to stroke both of us at the same time with our lengths pressed firmly against one another, our pre and my drool lubricating my strokes.
I moaned and moved my hips a

little. This was even better than I pictured.
“Oh my god yes…” He groaned and gripped my thigh.
“Mhh you like that?…” I moaned sexily for him.
“Fuck yes…”
This was the most intense feeling I had ever felt and I could already feel a deep hum of pleasure building from my lower abdomen at that moment. I could feel it coming. I didn’t want to yet though… not until…
I slowed down my hand and looked up at him, panting.
“I… did you want to… I want…” I breathed.
“You decided you want to tonight…?” He looked down at me lovingly.
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I nodded and took a deep breath. I was certain. It had to be tonight. Everything was just so perfect.
He nodded and reached over onto the dresser and grabbed the lubricant he had brought “just in case.” I felt nerves grip me but I knew I wanted this. I had never been more certain of anything in my life.
I wanted him inside of me.
I climbed off of him and while he prepared himself with a condom and ample lubrication I removed my shorts and my panties. My legs and private areas were saved completely smooth, and I must say I looked really good. I put a lot of effort into it, so I was proud of what a good job I did. I was so nervous. Shaking, obviously. He picked up on it and climbed back into the bed, leaning to kiss me as he did so.
I looked into his eyes and smiled a little.
“They say that it’s best for the first time if the reciever is on top… Is that what you want to do?”
I nodded.
He nodded back and laid down on his back, me straddling him shortly thereafter. He told me to open my hands and I did so. He squeezed lube into them and I knew what to do from there. I put it over my tight little puckering, nervous hole and pushed a finger inside. I was so tight from nerves. I managed to get one, and then two fingers inside of me, spreading the lube around as much as I possibly could in there. I took a deep breath and reached down and gripped him, ready to guide him inside. I couldn’t believe it was happening, but it was.
He rubbed my smooth thighs softly and smiled up at me.
“Take your time… and remember to relax and breathe.”
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I nodded and took a deep breath as I felt his tip prod at me, a little groan escaping his lips.
I lowered my hips a little more and felt it pressing against my rim, practically begging to slide inside. I whimpered and lowered myself more. It didn’t hurt yet…
I moved down a little more, and felt something give. He slid inside, and instantly a sharp, hard pain shot up through my form from my hole. I gripped his shoulder tight and gasped. He continued to rub my thighs with a look of concern on his face.
“Are you okay?…” He asked. “Just breathe…”
I wasn’t breathing. I couldn’t. It hurt. A lot. I finally exhaled slowly as I attempted to move further down on it. The pain didn’t let up, but I knew once this part was over with I’d enjoy it. I knew I would. Finally after sitting there for a few moments, I began to breathe again. I lowered myself more, and to my surprise, it started to hurt less. I managed to move all the way down until he was almost completely inside of me. Then I moved up… then I moved down… and it started to feel good… I know it’s cliche to say that it felt good the first time, but for me, it truly did. I started to get into it a little more, and I could tell he was picking up on my confidence because he began to focus on how great it was making him feel.
“Oh wow… ahh… you’re so tight… god damn…” he groaned through clenched teeth.
“Mhh… y-you feel huge…” I muttered as I tried to pick up speed.
It took me a moment to get my hips situated right but I really started to get into it and learn how to really ride him. I loved it. It didn’t hurt practically at all anymore. I think my rim had stretched enough to accomodate him and I leaned forward and kissed him, moving my hips up and down, taking him in as deep as I could go. He groaned against my kiss. I was fucking loving this. The sensation of him pressing deep inside, the feeling of his tip hitting me somewhere nothing had ever been able to hit… it was almost too much.
I moaned against his lips and picked up speed, by now moving at a moderate pace, gripping his shoulder. I was so proud of myself. I was doing it. I was giving him what I’d wanted to for so long. I moved up a little too far and he popped out of me.
“Ahh!” I whimpered.
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“Fuck…!” He growled.
I tried to get him back in but was interrupted by him gripping my hips and rolling me off of him. I bounced onto the bed and before I knew it he had flipped me over and I was laying on my stomach with a pillow under my hips, my waiting, swollen hole in the air for him. He pressed against it again.
I said something I never thought I’d say.
“I want you to take off the condom…”
It was dimly lit but I could almost feel his confusion.
“Really?” He questioned.
“Mhm…” I nodded.
We had both presented each other with proof that neither one carried any diseases. The condom was being used for other, less glamorous reasons, but at this point neither of us cared anymore. He just wanted me and I wanted him any way I could have him.
“You’re sure?” He rubbed my cheeks as he said.
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“Yes… please. I want to feel you, not the condom…” I gripped the pillow.
He rubbed down my back gently and I heard the telltale sound of the rubber popping off. I beamed to myself. I wanted him to cum inside. I wanted it so bad it hurt.
After he applied more lube I felt his fleshy, now exposed tip press against me. It felt phonominally better. All of my yes. He pressed it in more until I felt it slide in again. It hurt again, but I knew it was because of the angle we were at. I winced and he rubbed my plump cheeks gently.
“Still okay?” he said with concern in his voice.
I nodded.
“Mhm… just go really slow…”
He proceeded to press in to me further, and it seemed after he got past the initial rim it didn’t hurt as badly. Then he’d pull out, then push in again, nice and slow… I could feel him getting so deep… In a sudden moment of “I’m a guy and I can’t control my horny level” he pushed in all the way, balls deep.
I cried out. Not from pain, but from pleasure. I felt him hit something DEEP inside of me. It felt almost like I had to pee, but also pleasurable. My prostate. I gripped the pillow and he asked me again if I was okay out of concern.
“God yes, that felt amazing…!” I moaned.
He did it again, but not as hard. I moaned again for him, lip quivering. I had never felt something so good in my life. He leaned more over me, my legs benging and my toes curling as he began to push into me a little more quickly. I was absolutely in love with the senation and I wanted more and more. My soft, feminine moans and my delicate feminine body must have been driving him crazy because he picked up speed, sliding in and out harder until I could feel his hips slapping against my ass. I was moaning into the pillow and screaming at times. I knew the people the next room over could hear, and I didn’t care. Then… out of nowhere, I had a swelling, amazing, pulsing, sparkling, oh-my-god-what-just-happened, orgasm into that pillow underneath my hips. I clenched and bucked back at him as I came, and he responded by goaning.
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“Ohhhh yesss…. cum for me baby…” He growled.
I was. Oh god I was.
I felt him almost seem to grow inside and I knew that he was close too.
“Cum inside me please!” I moaned out.
“Oh I’m about to!” he groaned as he picked up speed, the excitement growing.
“Oh god yes, oh god baby ahhh!!!” I cried out as I felt him stop suddenly and bury himself inside.
He groaned and spilled possibly half the contents of his balls inside of me and I think for a moment my mind went blank. Perfection. I can’t describe it any other way. He groaned and lightly thrusted into me.
“Fuuuuuck yesssss…!!” I heard him grunt as he gripped my soft cheeks tightly.
I reached back and grabbed his hand on my ass and whimpered into the pillow, feeling his orgasm throb and then die down…
He panted for a moment, rubbing my cheek that had his free hand on it.
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I felt him withdraw very slowly…
He pulled out of me and I laid there, dumbstruck. I was in heaven. My body hummed and purred from the pleasure that had just been poured through it. I didn’t move for a time, just laying there panting. He moved out from behind me and laid beside me on the soft blankets, a huge, goofy grin on his lips.
I slowly turned my head to look over at him, shaking.
“Wow.” he chuckled.
“…Wow…..” I giggled.
He pulled me against him and spooned me, delicately kissing me on my cheek and neck and shoulder, rubbing his fingertips up and down my arm gently. I laid there, safe and warm in his arms, beaming. I was the happiest I’d ever been.
“Not bad for your first time, huh?” He chuckled again.
I giggled and kissed his hand.
“Not bad at all…”
We laid there for hours afterward, basking in it. He would pet me and kiss me, and we would go on about anything and nothing. I loved every second.
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The next morning I woke him up with my lips around it. We proceeded to have sex again, ending in a very similar fashion.
Not a bad first time at all.
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