How Nathan became Natalie Ch. 03

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Nathan aka Natalie enjoys a night with Kevin.
5k words
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Part 3 of the 6 part series

Updated 06/08/2023
Created 11/03/2017
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saintlycd
saintlycd
97 Followers

Friday came and after classes and eating a light meal it was a little after five in the evening when I paid for and checked in the room where I was going to meet Kevin. I gave myself plenty of time to get ready for him. I had decided besides wearing Jennifer's dress I would go even further and try my hand at completely dressing as a girl.

I purchased some new panties to wear that were red to match the sundress and a pair of sheer white thigh high stockings. I went with the white thigh highs because that is what my girlfriend wore sometimes when she wore her dress I was going to wear for Kevin and figured since she knew more about coordinating outfits better than I did; I would go with what she knew. The panties were lacey red boy short cut panties that were sheer red material were the lace part did not cover up. I did not need to buy a bra since the dress had the built in support for breasts, which I did not have naturally but due to the built in breasts' cups when I wore the dress it gave me some resemblance of having small boobs.

I even purchased a very cute satin, pink baby doll nighty set that was trimmed in black. The top was camisole cut with thin shoulder straps that was tighter around the bust area and flared out at the hem that would stop just above my pelvic area and had a sewn in black ribbon that tied just below the bust line to make a very adorable bow. The set came with pink G-string cut panties that left very little to the imagination. I bought the lingerie to wear as we slept and fucked some more once Kevin removed my dress.

I had also purchased some feminine scented body spray that was not overbearing perfume scented but had a soft feminine fresh scent as well as an extensive makeup kit that came with various shades or eye shadow, blush, base makeup, brushes and applying sponges and picked up four shades of lipstick and some mascara.

I had used the hair removal cream the day before so my body and face were already smooth but I did do a little touch up to my private area with a razor just in case. If Kevin wanted a girly looking sissy, femboy for the night I was going to go all out for him.

I gave myself plenty of time to get ready for my lover. Kevin said he would meet me in the room around eight that night; or so I thought I gave myself plenty of time. I cleaned myself and then showered, washing myself with Dove soap; ever since Kevin and I started our affair I had started using feminine soaps and lotions and deodorant. I styled my hair in a girlish style and once again used barrettes in my hair to hold my bangs in place, these were pink ones with butterflies on them, and started to work on my makeup.

My makeup was a disaster! I gave it four attempts and kept looking like a clown. I did not know how girls could make it look so easy and I was frustrated to the point of tears. After my failed attempts and running out of time before Kevin was to arrive, I decided to just wear mascara and a soft pink shade of lipstick (I really liked pink). After I was almost dressed I did see I had some time before Kevin arrived and at on the edge of the bed in my panties, thigh highs, and a tee shirt; I did not want to wrinkle the dress and would put it on when Kevin knocked on the door. My little penis was already rock hard while I waited and thought of what we were going to do that night and hopefully into the early morning.

Kevin was only about ten minutes late and when I heard the knock on the door I checked the peep hole to make sure it was him and grinned like a school girl with her first crush when I saw it was.

"Just a moment." I said and ran to the small wardrobe area of the room and put on my dress and then placed the bottle of anal lubricant on the night stand next to the bed; to have ready for when Kevin wanted to fuck me.

I took time to admire myself in the mirror and giggled when Kevin knocked again. I had to admit to myself I looked very cute and very feminine. I know people have told me in the past how "pretty" like a girl I was but I really never believed them but looking at myself in the mirror dressed as a girl, hair styled in a way a girl with shorter hair would style hers, and even the little makeup I wore; I looked good, very good! I even thought to myself "Heck Nate...no Natalie, you could go out like this and no one would know you were a boy". I looked at my bare feet and thought I should have bought some heels but too late now. Kevin knocked a third time to bring me out of my narcissistic trance and giggling at his inpatients I went to the door and opened it for him.

"About time." Kevin said when I opened the door and stepped aside to let him in.

"A girl needs to take her time to look good for her man." I smiled.

Kevin then took a moment to look at me, His eyes going up and down my body. "Fuck, Nate, you look hot. I mean wow, seriously. I thought you would look sexy in Jennifer's dress but damn you went all out huh?"

I smiled and took the hem of the dress in my hands and lifted it slightly as I wiggled my hips. "You like?"

Kevin grinned, "Yeah I like...I like very much, Nate."

I pouted, "Nate? Who is Nate? I am Natalie." I grinned at him.

I had decided when waiting for him I would give myself a girl name for tonight. After all if I was going to look like one, be treated like one, and fucked like one I should have a female name also.

Kevin laughed, "Ok, Natalie. Come here."

I walked to Kevin and he put his muscular arms around my thin waist and pulled me to him. I gave a small gasp and soon found his lips pressing on mine. I parted my lips and felt his tongue enter my mouth with more aggression than normal and gave a whimper as we kissed. I wrapped my arms around his neck and we stood in the center of the room making out with a lot of passion. When Kevin's hand moved to my butt I broke the kiss and plaid my head against his chest and started caressing it with my right hand; enjoying the feel of his muscles under his tee shirt. Kevin moved to kiss my neck and I giggled and moved away but still in his arms.

"Not so fast, handsome. I am not some cheap street whore. I am a very elegant escort and we need to discuss price and what you want for my services tonight and for how long."

It only took Kevin a second to catch on and he grinned, pushed me away gently, and sat on the bed. He looked up at me and smiled.

"I intend to do everything to you all night and fuck your brains out and you will do whatever I want."

I smiled, "All night is three thousand and bareback is three five."

"Done. Now get your sexy ass over here and stand in front of me."

Giggling I walked closer to the bed and stood in front of Kevin and smiled down at him. Kevin reached up and ran his hands up my thighs seductively and I closed my eyes and moaned at the pleasure of his touch. Kevin's hands going up my thighs lifted the hem of my skirt and I opened my eyes and looked down at him when his hands went under the waist band of my panties. Kevin looked up at me and smiled as he pulled my panties down a little to free my erect penis.

"Well what's this, Natalie?" He teased. "You seem to have a very large clit or a very small cock."

I giggled as I ran my hands over his head. I no longer got offended when Kevin brought up the fact my penis was small; he did like to tease me about it. I once asked Jennifer one night after she gave me oral sex if she thought I had a small penis and she told me she was not one to judge.

"The only other ones I saw have been in porn videos and those men get hired based on penis size I am sure." She said. "Plus from what my friends tell me it's really not the size of it anyway that matters." Then she kissed the head of my cock and smiled at me. "Yours is cute."

Then there was the fact I liked having a small penis when I was with Kevin. It made me feel much more feminine and more like a sissy boy for him; not that I needed much help in that area.

I looked down as Kevin wrapped his hand over my penis; I enjoyed watching my jerk me off and the way his large hand just completely swallowed my little sex organ. I moaned as he slowly ran his hand up and down the shaft to the head and then back down again. Once more I closed my eyes and then gave a loud gasp of pleasure as I felt him take me into his mouth. I placed my hands gently on his head, not to hold him there or to guide him; he did not like that, but just to be able to touch him as he sucked my cock.

"Ohhh...God...Kevin...that feels so good." I softly moaned out.

Kevin's hands were on my ass cheeks and as he gave me a blow job. It was not long before I felt I was about to orgasm and my lover must have sensed it as well because he took his mouth off of me and looked up at me.

"My white girl likes having her clit sucked?" He asked with a smile.

I took a deep breath, "Yes...oh God she loves it when you do that." I answered in a whiney, girly voice. I wanted to orgasm so bad but I knew from past experience that I was not going to cum until he wanted me to.

"Well more of that later. You got me so horny I want to fuck you now. Did you bring the lube?"

I giggled, "Of course." I walked to the night stand and got the lubricant, walked back to Kevin, and handed him the bottle which he placed on the bed next to him.

"Suck my cock a little before I fuck you." He told me

I smiled and got down on my knees between his legs and with Kevin's help I removed his pants and underwear. I took his large cock in my small hand and gave it a gentle squeeze to feel its hardness as I looked at it. The site of his penis excited me a great deal as did his body in general. I would often just look at Kevin when he was naked in our dorm room; when he got out of the shower or when he got dressed I would stare at his body and get aroused and seeing his larger cock, even when it was not erect and hanging between his legs I would get excited.

I looked at his large black penis as I stroked it and savored my desire to take him in my mouth and have him fuck my ass with it. Having him in my mouth and my "man pussy" made me feel so feminine and weak and I had a desire to have a strong masculine man take care of me; how I would dress pretty for him and I would please him sexually anyway he wanted me to. Kevin allowed me to admire his manhood for a few more seconds and then I parted my lips and lowered my head and took him in my mouth.

I felt the rush of sexual desire wash over me as I took just his head into my mouth and ran my tongue over him and tasted his wonderful cock. Kevin moaned and the sound of me pleasing him excited me even more; I felt I got just as much sexual pleasure out of pleasing him than I did when he pleased me. When I took my lover deeper into my mouth I looked up at him and he grinned back at me as he ran his fingers through my hair. Kevin allowed me to suck his cock nice and slow; enjoying how my mouth felt on his penis.

I gave him a slow seductive blow job for several minutes listening to him moan in pleasure as I gave my own whimpering moans of delight having him in my mouth. I placed my hands on his muscular thighs and used just my mouth to please him as he kept his hand lightly pressed on my head. After several more minutes Kevin pulled my head back and I looked up at him and made a pouty face causing him to chuckle.

"Want more of my cock in your mouth?" He asked me.

I smiled, "Yes."

"You are such a little sissy cocksucker, Natalie. I love it but I want to fuck you now. We got all night for you to suck my cock some more."

I nodded and smiled at how he called me Natalie. I wiped my mouth and stood up and reached behind me to unzip the dress.

"No...I want to fuck you while you wear it. It's sexy." Kevin stopped me. "Just take your panties off."

I nodded and removed my panties as he started to lubricate his hard cock. "Now get on top of me."

Grinning I lifted the hem of the dress, straddled Kevin, and bent over and he started kissing me with a great deal of passion as I took his slick penis and guided it to my tight hole. When I felt the head of his cock hit the entrance to my ass I slowly lowered myself on him. Still kissing him I gave a whimpering girlish grunt into his mouth as he entered me. As his cock stretched my little "man pussy" it hurt some but I did not care. I knew the pleasure I would feel of it soon. Kevin let me lower myself down slow and soon I was sitting on his lap and his cock was all the way inside me.

"Fuck, your pussy is so tight." Kevin said in my ear as he started kissing my neck.

"Uhh...thank...uhhh thank you, baby." I moaned out.

"Now fuck me nice and slow." He told me.

The pain was gone and replaced by the wonderful strange pleasant sensation and I lifted my small ass up a little and then back down slowly causing us both to gasp out. As I repeated the movement over and over the pleasure of him in my ass increased and I started to go a little faster. Kevin reached up and pulled the bust line of the dress down to expose my hard nipples.

"Not so fast, baby." He told me as he pushed my body up and wrapped his arms around me.

I nodded and was now sitting up on top of him and resumed my slow movement up and down on his cock. God it felt great! Before Kevin fucked me that first time I never understood why people enjoyed anal sex; being naïve about it. I never understood how some girls and gay men could enjoy it; but now I understood. To me it felt wonderful and not just that; I started to crave it.

I know it was not the same feeling or desire a girl to have her pussy penetrated when she was aroused, but not knowing how a girl feels when sexually turned on and my desire to be a girl for Kevin gave me the yearning to be fucked in my ass. I myself even thought it was strange, but when I got sexually aroused I not only wanted my penis stimulated and to cum that way; most of the time I had a stronger longing to be fucked in my tight hole. Even when Jennifer and I made out and she gave me oral sex I wanted to be penetrated anally; much to my shame. I felt guilty about that desire when I was with her. When I masturbated now I would often finger my own ass and it would make my orgasm so much more intense.

I gave a loud gasp of pleasure when Kevin rose up and started sucking my nipples. The sensation was incredible and I had to mentally fight my own desire to ride his cock harder.

"Ohhh...ohhh God...Ohhh, Kevin...please...please let me do it harder...please." I begged my lover.

Kevin took his mouth off my nipple, "Not yet, baby, we got plenty of time tonight. We are going to have a lot of fun."

"Ohhh...ok...ok...ohh fuck...you feel so good inside me." I gasped out and wrapped my arms around his head and hugged him to my chest as he started sucking my nipples again; going from one to the other repeatedly.

As I rode Kevin's cock slowly he sucked my nipples causing me to make gasping soft moans. My little penis was sticking out and erect over his stomach. After a few more moments Kevin lay back down on his back and as I bent over to kiss him he gently pushed my body back up.

"Don't move. Just sit there on top of me." He told me.

Kevin reached over and picked up the bottle of lubricant and dribbled some over my hard cock. He then took my little cock in his large hand and started to stoke it slowly causing me to moan out loudly. I raised my ass up a little to resume fucking him, but he grabbed my hip with his free hand.

"Ut uh. Don't move." He told me again.

Whimpering I nodded and lifted the hem of the dress higher and watched him jerk my lubricated dick. It was less than two minutes before I came. I gasped and moaned and made whiney sounds of pleasure as my penis exploded; spraying my cum all over Kevin's stomach, chest, and much to my dismay Jennifer's dress; which at the time in my blissful state I did not care about.

After my orgasm ended I collapsed on top of Kevin, smearing more of my own fluid on the dress, but again I did not care at the time. I was panting in short shallow breaths as Kevin kissed my neck and ran his hands over my ass cheeks.

"Umm I could feel your ass around my cock when you came." He chuckled in my ear.

I lifted my head and kissed him hard, "That was amazing. Thank you."

Kevin ran his fingers through my hair and smiled as he looked at me, "My pleasure, Natalie. But now it's my turn."

Kevin lifted me off of him and tossed me on the bed and I gave a squeak and then giggled as I rolled over onto my back. I was still giggling when Kevin lifted the hem of my dress higher, spread my legs, and lifted them up to expose my "man pussy" to him. I bent my legs at the knees as my lover entered me in one slow, long thrust. My hole was already stretched so it did not hurt but felt so good. Kevin's large body got on top of mine and he wrapped his muscular arms around me. One around my back and the other cupping my ass; just one of his large hands covered both of my small girly ass cheeks. I wrapped my arms around his large back and gripped him tight and he started fucking me.

Kevin started slow and gradually picked up his pace. As he was fucking me I was moaning and gasping and whimpering repeatedly in the wonderful sensation of him fucking me as he gave the occasional masculine grunting moans. In between his moans of pleasure, Kevin told me how tight my "pussy was", how good it felt to be inside me, and how he enjoyed fucking his sissy, white, slut. When he started fucking my harder my moans turned into louder screams of bliss and I called out to both Kevin and God often in between my screams. Kevin placed both his hands on my ass and started fucking me even harder as my hands clinched tight on his back. I cried out several times how wonderful he felt inside me and even begged him to fuck me harder. As he fucked me as hard as I thought was possible for him I kept crying out in my own enjoyment of being fucked as he grunted in his manly exertion.

Years of playing football, the intense physical practices he endured, and his strenuous workouts at the gym gave Kevin incredible stamina and he had what I considered unbelievable "staying power" before he would orgasm; but of course I was naïve about another man's self -control during sex. Kevin was the only man I had ever been with sexually and my own "staying power" was almost nonexistent; but I have seen porn videos where the man could go on for a long time before he orgasmed and Kevin was that way. He kept fucking me hard.

It did not hurt; quite the contrary, it felt wonderful and I wanted him to keep going forever. I knew by the end of the night my ass was going to be sore, but I did not care. I just wanted my strong black lover to fuck me like a girl over and over again. I not only wanted to be his sissy, twink, slut; I wanted to be is submissive female lover to do anything he tells me and to please him anyway I could sexually.

I don't know how long he kept fucking me, but like all good things it had to eventually end. I felt Kevin's body tighten and he drove his cock hard and deep into me and gave a series of grunts as he came. I cried out in bliss as I felt his warm cum spray into my ass. I really enjoyed the feeling of Kevin cumming inside me. He held his cock deep and I could feel it pulsing inside me. He came hard and I could feel how huge his load was as it exploded in me. After he was finished, Kevin collapsed on top of me and we panted for air together; his sweaty chest pressing against my skin, exposed from where he had pushed the dress down to bare my chest and nipples. I held him tight as I kissed his sweaty neck and licked his perspiration off his face. I loved his manly scent and taste.

"Fuck that was great." Kevin told me after he caught his breath. He raised his head and smiled at me, "Your pussy is so good, Natalie."

"Oh God you fucked me silly." I teased when I caught my own breath. "It felt so good I didn't want it to end. My legs are still trembling." I then gave a little moan as Kevin pulled out of me chuckling.

saintlycd
saintlycd
97 Followers
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