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Becoming Anthea Part 2

"Anthea story continues."

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My name is Anthony; I am twenty-two years old and live with my beautiful girlfriend Zoe. As you have read I have dark hair and dark eyes and I am clean shaven. Zoe is older than I am by a couple of years and is the driving force of our relationship. I am what many call a cross-dresser: a guy that gets great sexual satisfaction from dressing in women’s clothing.

Of course, my girlfriend knows all about my cross-dressing. In fact, she encourages me to cross-dress. Once a week, generally on a Monday, Zoe and I have a wonderful fuck, then she shaves my cock and chest and chooses a sexy outfit for me to wear. She does my makeup making me look as feminine as possible, which isn’t hard. She curls my hair and then takes me out to dinner.

We usually end up in a bar, with guys drooling all over us. Not many guys or girls realize that I'm a guy and I get flirted with by many. Zoe gets so turned on by parading me around like her little slut. This gets her so horny that when we get back home, I get to have sex with her three or four times.

Every time we go out with me dressed like a girl, I get called Anthea. It is the only name I am allowed to answer to and it is the only name Zoe calls me. As if to cement my new name, Zoe got me a necklace with the name Anthea on it.

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It was nearly three months since Zoe first caught me dressed in her underwear and she has since taken me out weekly. She has bought me loads of sexy clothes for me to wear on our “girls” night out.

It was a Monday like any other. I got home earlier than she did and waited impatiently for her to arrive. When she finally did get home, she sent me to get undressed. When she came into the room, she was carrying a small bag. She saw my curiosity and smiled.

“That’s for later. Let’s get you shaved and bust your nut, so we can have a good time later. “

As per her Monday ritual, Zoe got the shaving cream and razor out. I lay back closing my eyes, I never could get used to feeling a straight razor so close to my balls. I knew she wouldn’t hurt me, still, it made me nervous. Once my cock and face were clean shaven clean, she poured oil over my cock. Her hand slid over my cock, gently jerking me off. Generally, Zoe never lets me cum during the week; she wanted me to save my load for our Monday’s fun.

She really enjoyed jerking me off, enjoying her power over me. I let her do as she wished. I loved her and knew that not many other girls would let me enjoy my kinks, not like Zoe did anyway. I groaned loudly, her hand gliding easily up and down my cock.

It didn’t take long for me to get worked up; she knew exactly how to jerk me off. She expertly teased the tip of my cock, making my whole body rock with pleasure. She loved teasing me and slipped a finger against my anus, a sure way to get me to shoot my load. As soon as her finger slipped past my sphincter I shot my load. Before it could go everywhere Zoe clamped her mouth around my cock, swallowing my thick strings of cum. She sucked hard on the tip of my cock taking in every last drop.

Zoe kissed me lightly on the lips and told me to get in the shower, and she would join me in a second. I went into the bathroom and stepped into the shower; the water was hot and soothing. Zoe joined me, her naked body pushing up against mine.

I loved her body, secretly wishing that I looked like her. She had wonderful breasts, belly, and ass. She was a goddess to die for and I would do anything for her. In the shower, we made out slowly and passionately as we both groped and caressed each other. Zoe put an end to our playtime in the shower and told me to get out and dry myself properly.

I walked back into the bedroom to find my clothes waiting for me. I picked up a black lace teddy and my silicone bra fillers. I slowly slipped on the teddy, tucking my cock between my legs. I fastened the gusset s and inserted the silicone fillers. For those that don’t know what silicone fillers are, they are triangular silicone pads that give off the illusion of a bust. For a “girl” like me, it gives the impression of having breasts; for a normal girl, it gives the impression of bigger breasts.

Zoe walked in the room and gave me a wolf whistle. Her hand slid over my ass, giving me a small pat. She helped me adjust the teddy, making sure my “breasts” looked real. She chose a cute green and yellow dress for me to wear, making sure I looked good in it.

She made me sit at the dresser as she slowly did my hair. She used a hair straightener to style my hair, keeping it in place with bobby pins. As usual, Zoe made me look extra feminine and I could see my features starting to take on the girly look. Zoe turned me around to face her and slowly started to apply my makeup. She is such an artist and always makes me look good; this time was no different. She made every detail on my face feminine with soft, subtle colors.

Zoe gave me a peck on the lips and turned away to get dressed. As she dressed, I stood up and looked at myself in the full-length mirror; I looked so hot. If it wasn’t for the teddy keeping my cock tucked between my legs, I would have a hard on.

“Here baby, these are for you.”

I turned around to see Zoe holding out a pair of yellow two-inch heels. I had been practicing in her heels at home for a few weeks and had gotten my walk down pat. I slipped them on; they were a perfect fit. I smiled and looked at Zoe once again, my cock straining against the teddy. Zoe wore a dark blue backless mini-dress that hugged her body and showed off her amazing ass.

As we made our way out for a fun evening, I couldn’t help but wonder about what was in her small bag.

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The evening went by quite quickly; we went to dinner and then for a walk. A few guys looked at us, ogling at our sexy bodies. It didn’t take too long for Zoe to decide that we should go back home. Zoe led me back to the car and we drove home in silence.

I had this weird feeling she had some kinky shit planned for us, and I was so right.

As we got in, Zoe went right into the bedroom and returned holding the small bag. I knew that bag was going to be involved. I watched as she upended the bag, spilling its contents out onto the couch. To my shock and amusement out fell an assortment of sex toys, all still in their packaging.

“Tonight Anthea, I am going to make you feel like a real girl. I am going to use every single one of these toys on that sexy ass of yours. Then I’m going to finish by fucking your ass with this strap-on.”

Zoe walked over to me and kissed me.

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Her tongue slid into my mouth and we slowly made out. I felt her hand slip up my dress, unclasping my teddy, letting my cock free. Her hand gently wrapped around my cock and she gently jerked me off, getting me nice and hard.

“Take off your teddy but leave on your dress. I have something exciting for you to experience.”

I did as I was told, having slight trouble trying to take the teddy off. I did it, though. Zoe picked up what looked like a plastic stick with a ball on top. Zoe told me it’s called a wand. She plugged it into the socket and switched it on, and it started a low buzzing.

Zoe hiked up my dress and gently placed the ball against the underside of my cock. Fuck, it felt good. I’d never felt anything like it. The vibrations seemed to go right through my body, starting from the tip of my cock. Zoe smiled and pushed me back onto the couch. She lifted one of my legs, and without warning pushed the ball part of the stick against my sphincter. I have no idea what happened, but the vibrations made my cock spasm, it felt like I was going to cum right there and then. Zoe pulled the wand away and giggled, she chucked it on the bed and pulled the plug from the socket.

“Get onto all fours, I have two new toys that I am going to use on you, I know you’ll love them. Also, I am going to milk you till you cum for me. I know how much you love that.”

I got onto all fours for her, my cock sticking out. I knew she was going for the lube. She kept a small bottle on her bedside counter. I felt the cold trickle of the lube as she squeezed some onto my waiting butt. I felt her finger work the lube into and around my ass, dipping a few fingers into my hole. I closed my eyes, enjoying the sensations she was giving me.

I felt a hard piece of plastic against my sphincter and looked back. She giggled and showed me the toy she had in the hand. It was a long plastic toy that looked like it was beaded together as one long piece. At the bottom, where she held it, it had a battery pack.

“Baby this is our new toy, it’s called an anal wand. Guess what it does?” She giggled that laugh I love so much. “You will love it, I promise. I am going to milk you at the same time. By the way, your ass looks so good tonight.”

She squirted lube on her hand and gently traced her hand over my balls and to my cock. She covered my cock in lube and then held it firmly in her hand. As she held my cock I felt her slowly ease the toy into my ass, one round bump of the toy at a time. Slowly I could feel my ass getting filled, as her hand started to slowly glide over my cock.

The toy seemed to go far into my ass as she switched it on. I could feel it vibrating all the way in my ass, feeling it to my core. Slowly she started to slide it in and out of my ass as her hand reached beneath me gripping my cock.

Slowly, her hand slid up and down my shaft as she fucked my ass with the toy. I closed my eyes, savoring the feeling I was getting. Zoe worked me good, jerking me off and fucking my ass. Slowly I pushed back against her, feeling her work the toy deeper into me.

Zoe pushed the toy deep into my ass. I grunted as she let it go, leaving it vibrating in my ass. Her hand jerked my cock, gliding her fingers all the way to the top and squeezing gently on my bulbous head. She let go, pulling the toy from my ass.

I sort of collapsed onto the bed and as I heard rustling behind me. I roll over to see Zoe stripping off, I love her body and she always looks hot naked. She smiled at me as she picked up large, thick red dildo. I looked at her shocked, I knew what she was going to do with it.

I watched as she attached the huge dildo to a black harness and slip her legs into the straps. The strap on looked impressive, I could feel my ass clench in fear. Zoe just smiled and smothered her “cock” with lube.

“Baby, I’ve always wanted to know what it would feel like to fuck a guy, now I’m gonna fuck you and see how we both enjoy it. I think if we both like it I may see about turning you into Anthea full time.”

Zoe got behind me, rubbing some lube into my ass. I felt her hand grip my dress which was still hanging around my midriff. The tip of her toy pushed against my ass as I grunted loudly. I felt it slowly push into my ass as Zoe pushed her weight on top of me.

I could feel her breasts against my back as she slowly started to “fuck” me. Her hard, red cock slid deep into my ass. It was the longest and thickest thing she had ever stuck up there, it felt great. She held my hips tightly and slowly slammed her “cock” deep into me.

She was rough, slamming hard and squealing in pleasure and making me grunt. She pulled her cock out of me and told me to lay on my back. She lifted her leg up and slid back in. Her hand wrapped tightly around my cock as she slowly started to pound me once more.

I closed my eyes as her hand slid easily up and down my cock. She started getting rougher with me, slamming the strap-on deep into my ass. Her hand didn’t let go of me and I could feel myself getting close.

“Yes, Anthea, cum for me. I want to see you shoot your load all over yourself. That’s my little slut.”

The way she talked dirty to me really did something to me. My ass clenched around her “cock” as my cock erupted one of the biggest loads I have ever had. A large, thick glob shot from my cock landing right on my own face, the rest landed on my belly and chest.

Zoe giggled and she pulled the dildo out of my ass, making a loud popping sound. She pushed me back on the bed and with her finger, scooped up my cum that had landed on my face and pushed it into my mouth. She then pushed the strap-on into my mouth making sure I would not spit out my cum. I could taste a nice mix of my own ass and cum, it tasted better than I thought it would.

She pulled the dildo from my mouth and kissed me passionately. She kissed my neck down to my belly and chest, sucking and licking up all my cum. She then leaned forward and kissed me again, I could feel my own cum pouring into my mouth from hers. We kissed for ages, not wanting to let go of each other.

We both lay back exhausted, Zoe pulling off her strap-on and lying flat on top of me.

“Anthea, what do you think about being a girl full time? Maybe we can make a transition. I would still love you just the same, I think it would be so hot if you were my girlfriend.”

I mumbled something, not knowing if she were serious or not. I fell asleep with her nuzzling up to me. I knew it would not be the last time she used her toys on me. I was actually excited.

To Be Continued

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Written by Sholbin83
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