Author’s note- all persons are over 18 years old. I’ve written this story with a similar plot line to a lot of other stories on Literotica (best friends getting it on with one posing as a female) except for a little kink at the end. Sorry for the spelling and grammer mistakes, I’m not a writer and the story was a quick write.
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I was just getting out of the bath when the pain hit me. I almost fell because of the soreness in my leg was so bad to stand up. I had injured it playing highschool football and the doctors told me I would have to relearn to walk since my injury had damaged the nerves in the calf to the ankle. I was in bed for months recovering from surgery and my parents made sure I kept up with my studies.
My best friend (and now lover) Shaun was always over to my house, bringing my homework and hanging out playing video games until my parents came home from work. He would help me out of bed into my wheelchair the first couple of weeks of my recovery and then take me around the house or outside in the back yard to enjoy the sunshine. We had grown up as neighbours, sharing much of middle and now highschool life together, both of us being bright students and leaving our parents not to bother us much about our studies. We had shared our 18th birthdays at the end of summer before school started and couldn’t wait to get back in the social life of our peers.
It was early in the last year of high school when I first saw Shaun’s manhood in the locker room. Flaccid, it still hung about six inches over a big bag of balls underneath it and I kind of got excited looking at it. I had realized early in my life that I was bisexual and by searching the internet for information about how I felt sexually, I was leaning more to being feminine and thinking how I could make myself girly.
It was also during that time before my injury when I would raid my older sister’s wardrobe, dressing up and having fun when no one was around. When my sister went off to college, her room became my sanctuary to become the girl I felt I was inside. Panties, bras, and dresses and even a pair of breast forms (my sister had been small in that department until she hit senior high). Everything was there to make my fantasies become real and with her makeup table full of cosmetics, I became quite good at putting my makeup on. I would stare for hours at the new me in the full length mirror, twirling my hair and swishing my hips and bending over to display my ass in some sexy tight outfits. I would relieve my excitement with thoughts of Shaun’s cock in my hand and mouth and then clean up, putting everything away and return to my bedroom satisfied for the day. It was so much fun, UNTIL!
One day Shaun came over unannounced, opening the unlocked front door quietly and came up the stairs to my bedroom. My bedroom door was open, but he didn’t find me there, so he called out my name.
“Jake, were are you?”
I had just finished getting all dolled up when suddenly he was standing in the door to my sister”s room. Like a deer in the headlights, I froze in my girly attire as he scanned my outfit with his eyes.
“Wow dud, what’s going on?”
“Sorry, please don’t look at me.” The tears started to flow from my downcast eyes as I stood there trembling. It seemed like a lifetime before another word was said between us, but Shaun spoke first, saying,
“My, don’t you look lovely, and kinda sexy too.”
I raised my soggy eyes to his and realized he wasn’t disgusted with the way I looked or the idea of his best friend was a crossdresser. We stood staring at each other until I had the nerve to speak,
“I”m so sorry Shaun, you scared me. You aren’t going to tell anyone please. I only do this because I sometimes feel a need to be the other part of who I am. I feel like a girl Shaun. Does that bother you?”
“Well, it certainly is a surprise. And I must say, a beautiful one at that.”
I blushed as my tears stopped and I dabbed the wetness from my eyes, staring at him as my body shook with nervous excitement.
“I understand if you don’t want to see me anymore,” as I cast my eyes down to look at what I was wearing this time when he had surprised me. I had on a matching bra and panty set under a body clinging black dress with a sheer pantyhose and a pair of my sister’s heels that actually fit me. My outfit showed off my legs and butt in a sexy female contour and with the breast forms filling out the top of the dress, my body had become female. I had done my makeup prior to dressing and had put on some earrings and necklace to complete my look. My long hair was loose around my face and hung down over my eyes as I stared at the floor.
“What do I call you honey?”
I looked up thru my hair and then pulled it over my ears out of the way before I said, “I liked to be called Cara” I told him.
“Well Cara, it’s nice to meet you. I’m Shaun and I was wondering if you’ve seen my best friend Jake?”
“Oh sure, he left for awhile, samsun escort something about hanging with some of his friends and won’t be home til later.”
“Good, I can spent time with you and won’t have that hounddog getting in my way of getting to know you.”
I let out a girly sounding giggle at his pickup line and stood still as he crossed the room and stopped in front of me and holding up his arms for a hug. He could obviously see I was really fucked up about exposing myself like this and I guess he wanted to ease some of the tension my body was displaying. I gingerly stepped between his arms and felt them close around my arms and shoulders, pulling me into his body in a comforting embrace. He looked me in the eyes and asked,
“Is this alright Cara? I don’t know what I’m doing so you’ll have to help me, please?” He was my best friend and now I also didn’t know what to do. We were both 18 year old virgins since neither of us had dated or had any girlfriends since we started high school. My arms wrapped around his waist, squeezing him to my shaking body and nervously looked up at his handsome face,
“Shaun, we’ve actually known each other for a long time. I have been hidden from you, but Jake, he’s even seen you naked and then something changed inside him after that. Now, you’ve seen me as I really want to be. I’m a girl who has feelings for you, but I could never tell you because of the shame it would bring on me and my family if everyone knew of my other self. Aren’t you freaked out about me dressed like this? Maybe I should change and we’ll never talk about this to anyone.”
I went to release him so I could change, but he held me tight,
“No, please don’t change. I just met you and I’d like to get to know you better.”
He leaned down and placed his lips to mine. I wasn’t expecting him to do something like this and I had never experienced kissing someone, so I just let him have some fun until it felt warm in the room and my girly mind took over as I started to kiss him back. Our tongues found each other as we touched each other intimately for the first time. I could feel his manhood straining in his pants as we crushed our bodies together, my cock getting hard and slipping out from between my thighs were I had tucked it. I got bold and pushed my own firm groin into his, wiggling my hips as I enjoyed these new sensations of having our cocks together. Suddenly, everything I had been dreaming about was happening and it felt good. He broke our kiss and said,
“Well, let me have a look at you. Turn around and show me that perfect ass you’ve got.”
I was getting excited to show him my girly outfit so I turned and presented him with my rounded tush, bending slightly to emphasize my girlish figure.
“Wow, Cara. I can’t believe Jake never told me about you. You have a perfect ass.” With that said, he came and placed his hand on my cheeks and massaged me, squeezing my globes and causing me to take a deep breath from the excitement he was giving me.
I wanted to continue our play acting and turned back to face him noticing a big smile on his face as I pulled him into another kiss. I had to touch him, his cock was something that never left my mind after the first time I saw it. I reached down between our bodies, finally gripping it and feeling it’s length. (OMG, it’s huge!) By now, his hands were squeezing my ass and lifting me up until I was standing on my toes. The strangest feeling came over me as I felt some wetness between my legs and realized I was leaking in my panties as I enjoyed the sexual heat between us.
I wanted to show my feelings for him (Finally!) and broke our kiss so I could undo his pants and letting them fall to the floor. Gripping the band of his underwear, I slowly slid them down to reveal his 8″ wonder. It was magnificent in it’s full sized glory. I wanted him and reached down to hold the first cock other than my own and began to jerk him off, feeling the big veins that ran the length of it and the soft spongy head that was wet with his excitement.
(Oh My, what’s a girl to do. Tee Hee!)
I slowly slide out of his arms and kneeled so his cock was level with my face. My fantasies had come true as I slowly stroked his beautiful manhood, my body and mind wanting this, being his girl and giving him pleasure. Opening my mouth, I sucked his engorged head past my lips and tasted precum for the first time. He hadn’t said a word as I experimented with his cock. I licked and sucked until I felt his hands on my head, holding me still as he began to hump into my face. I had only taken about half of it in my mouth, but each stroke pushed that soft head against my throat until suddenly I opened up and he sank his whole length completely into my body.
I couldn’t breath and panicked, pushing his torso away so I could inhale some oxygen or I’d probably black out. I looked up at my friend with watery eyes and a smile, opening my mouth for more. After a few more pokes, I had become a urfa escort deep throat girl, enjoying giving him this awesome blowjob as my girly mind concentrated on making him cum. His balls were in my hand when I felt them tighten and the first pulse of his sperm was sliding down my throat. I was so excited that I was sucking my best friend’s cock and had lifted the hem of my dress to fondle myself, feeling the dampness he had caused as I sucked more of his baby batter. I pulled back a little and the next jet of his juices filled my sucking mouth with a taste of his seed. I looked up and saw his eyes closed as he orgasmed, my need to pleasure him complete as more creamy sperm filled my mouth.
The moment I had fantasized about for so long had happened. I had sucked cock and it was my best friends. It filled me with another need as I rubbed my panty covered clit until I shook with an amazing orgasm, filling my panties until I was dripping on to the floor. I was moaning around his dick as I came, my body shuddering in orgasmic pleasure when he finished and softened. I had cum so hard that I felt a little faint from our coupling and I had to lean down to let the blood return to my addled mind.. Shaun picked me up into his arms again, whispering sweet things in my ear as I tried to calm myself. I looked him in the eyes, licking my lips with satisfaction that I could make him cum,
“That was fun Shaun. I’ve never done that before, sorry if it wasn’t very good.”
“Honey, that was amazing. I know you’ve never done that before. How did it feel?”
“It was something I’ve dreamt of after the first time I saw you naked in gym class. Your cock makes me wet and I have wanted to kiss and suck it for a very long time.”
“Well, we will have to do that again, but what about you? Don’t I get to play with my new girl friend?”
“Hmmm, I don’t know what I’m supposed to do. I don’t have a pussy, but I do have a pretty big clit.” I giggled at that reference, feeling the very damp panties between my thighs as I moved my legs.
“Why don’t you let me figure that out.”
He guided me to the bed and laid me down on my back with my legs over the side. With a slow motion, he lifted my dress high enough to see my soaked panties.
“My, My. It looks like you’re really turned on, your panties are soaked and what is that little thing leaking under them? Can I have a look honey?”
He reached and pulled my wet panties down off my legs. Now he could see the real me, but I didn’t care. I was the girl and I was wet for this man who seemed to like what he saw. My cum covered clit had shrunk to it’s normal 2” and my sac was just a soft bit of flesh underneath. I had learned to tuck and sometimes my balls would just stay inside me which helped smooth the look of my panties. He touched me gently, getting his fingers wet and tasting my cum as I watched him kneel between my legs. He held my sex, massaging my juices into my skin as I became hard again and when he pulled the folds of flesh down to expose the crown of my clitty, I was whimpering with arousal as more fluids leaked onto his fingers.
I was moaning on the bed with my eyes closed, enjoying being touched by him as my reality was lost in pictures of my wet pussy being fingered and teased with. I suddenly felt his lips kissing my clit and then sucking me into his mouth. I was in heaven as he easily took all of my girlhood and soon had me bouncing my hips to fuck his mouth. I came, squealing like a girl as he held my ass cheeks and never let his suction stop until I was drained and left as a puddle of flesh on the bed.
After I came back to my senses, shame took over and I quickly sat up, grabbing my discarded male clothes and ran to the bathroom. Shaun didn’t follow and only shouted out his apologies as I changed back into Jake, shaking with nervous tension that I let something like that happen between us. As I calmed down and looked into the mirror, I washed the makeup from my face as a smile slowly crept onto my lips. I knew I wanted more because I had really enjoyed my first blowjob. And Shaun had accepted me for who I really wanted to be and it only made me feel more girly than ever before. I didn’t know if what had happened between us would ruin our friendship and wished I could hide myself from him and return back to our normal lives.
I exited the bathroom and returned to my sister’s bedroom, tears starting to form in my eyes as I looked at Shaun laying there with his eyes closed and wished this had never happened. (Not really) I didn’t want to lose my best friend because I sucked his cock dressed as a girl, even though he really enjoyed it and I felt amazing when he sucked me too. I returned the clothes to their drawers and turned back to him,
“I’m sorry Shaun, I can’t do this to you. Please don’t tell anyone.”
“Jake, you’re back. You won’t guess who I just met. Her name is Cara and we seemed to hit it off. She’s beautiful and has the nicest ass. I wished she sinop escort didn’t have to go because we were having so much fun. Do you think I can hang with her again sometime?”
“Really Shaun, she probably ran out of here after she saw your python of a dick.”
“I think she really liked me Jake. We kissed and I held her perfect ass in my hands. She even seemed to enjoy giving me a blowjob. What do you think of that buddy?”
“She must have some slutty traits to suck on your monster. Was it good for you?”
“Oh hell ya. Soft lips and she could even deep throat. Sucked me clean and swallowed every last drop. My perfect girl. I hope to see her again real soon.”
“If I bump into her, I’ll let her know you’re pining away for some more lovin’, ok”
“Please do that. Well, now that you are here, let’s play some games of something.”
We didn’t bring up Cara again for some time. Both of us hanging out like normal, doing our studies and being just two buds together. It was after my accident that things changed between us. Shaun had dated a few girls during the latter years of high school and I hung back from any kind of relationships. I missed being in the change room after gym, oogling the boys cocks as they showered and dried off. But my desires were for Shaun and I didn’t want to upset his sexual foraging among the cute girls in school or me being jealous because I wasn’t that girl he was taking to bed. When Shaun broke off his relationships, he turned to Cara to give him some relief and she would dress up and give him a satisfying blowjob. This went on occasionally through high school but nothing else would happen between his.
When I could get up and around the house on crutches, I eventually got back into my sister’s room when no one was home. I would dress up again and have a perfectly wonderful day being the real me. It was one of those days that changed our relationship when Shaun caught Cara laying on her sister’s bed. I was wearing a bra and panties under a short nighty with some stay up stockings, enjoying music with my headphones on and my eyes closed so I didn’t notice he was there. My hands were inside my panties and I was close to filling them with my juices when I felt the bed move. I tensed in surprise and opened my eyes to see Shaun laying beside me nude.
“HI Cara.”
I turned off my music and looked at him, my face flushed a crimson red as I oogled his toned body.
“Shaun, what are you doing?”
“I’m here to help” he said with a grin. His placed his hand over mine and squeezed my fingers into my quickly softening clit. I tensed and went to pull back from his touch, but he held me tight and said,
“Keep going honey, I want to see you cum.”
My hand began working my clit again as his fingers interlaced with mine. Both of us were now rubbing me back to hardness as I laid back and closed my eyes in surrender to his manhandling my crotch. I felt his hard cock brush my thigh and my girly instincts were to reach out and touch it but he still held my hand in place so I just continued pleasuring myself. He started to kiss my shoulder and then my neck, tingles rushing thru my body as I laid there and let him have some fun with my body. The tension was building inside me as I felt vulnerable laying beside him, but the erotic thoughts I was having pushed me over the edge and I came, moaning and squirming on the bed.
I floated back from my orgasm and again felt his manhood resting on my leg as he leaned in to kiss me. Letting go of my hand, he grabbed my bra and squeezed it like I had some real flesh inside it as I felt his kisses get more urgent. I rolled to face him and wrapped my arms around his neck, pulling him into our frenzied kissing. I wanted him and his cock , so I reached down and held him, relishing it’s size and hardness.
We hadn’t gone any farther than giving each other blowjobs and I was still a virgin. Shaun told me the he had bedded some of his girlfriends and surprised me by saying Cara would be a good fuck. I had to punch his arm as he started to laugh but my inside were telling me that Cara wanted something more also. But I wasn’t a girl. How would things happen between us if he wanted more.
He rolled on top of me as we made out and his weight felt comfortable as I sank into the bed. His hands roamed everywhere over my body, even pinching my nipples when he slipped his hand under my bra. I felt my clit getting hard again as his cock rubbed my sex, agonizing whimpers coming from deep inside me. He slowly kissed down my stomach and then I felt his breath cooling the wetness between my legs. I closed my eyes as my thoughts floated off to a picture of Shaun eating my pussy, I was the girl who was going to give up her virginity and it was going to be with her best friend.
He kissed my panties sending a electric spike thru my core and I moaned loudly as he teased my body. Pulling my panties down, my clit stood up, glistening with my dampness and he quickly sucked my entire length into his warm velvet mouth. OMG was all I could whisper as he pleasured me. I felt my second orgasm building to release when he suddenly stopped. I opened my eyes and looked at him as he sat back and started to get off the bed.
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