My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to pick her up at the airport and enjoy the weekend together. Zakk is in his first year of college he is studying to be a make up artist for stage and screen. He and I have not really gotten to know each other and this was to be the weekend where we did that. Annie and I were also going to tell him about our plans for a fall wedding.
It had been several months since I had seen him and he had let his hair grow long. He had thin golden blonde hair that now came to his shoulders. It was tied back in a pony tail. He was tall and thin with a feminine look to him, even the way he walked. But he kissed his girlfriend good bye, I let it go.
As we were pulling away from the dorm his phone rang.
It was Annie.
She was snowed in and was not going to get out of the city until tomorrow at the latest. She told us to have a good evening with out her and she would fly in tomorrow.
Zakk and I grabbed some take out sushi and headed for my loft in the downtown area. As we ate we made small talk and tried to find a way to break the ice. I asked him if he wanted a beer but asked for wine instead. So the two of us had a glass of wine as we finished cleaning up after eating.
I looked out the big window that faced out to the West and could see cloud and darkness rolling in. I feared the storm that trapped Annie was heading to us from the coast. I settled in to watch some television and Zakk said he was going to his room to check e-mail and do home work. I finished my wine and surfed for a bit not finding anything of interest on. So I grabbed the paper and looked through the entertainment section and saw there was a showing of an old Bond movie at a local cinema and thought a guys night out might be in order. I folder the paper and walked to the room Zakk was using for the weekend. It was actually my office but the couch pulled out. When Annie and I marry we plan on buying a house that has a room for him. But right now he has to camp out in my office.
I knocked as I opened the door quickly There standing in the middle of the room was my future step son his hair was down and he wore a red lace demi cup bra and matching bikini panties. My jaw dropped as he twirled in front of the mirror on the inside of the closet door to see his ass.
He had done his own make up and he looked beautiful with his flaxen hair framing the earthy colours he had used to pretty himself up. He had no body hair I could see and dark red lipstick on.
“holy fuck knock next time” as he tried to cover up with the blanket I had left out for him.
“Zakk it’s okay I am not mad or anything, just taken off guard is all” I softened my face and stance to make him feel easier. “does your mom know about this?”
“uhgm no, No one does I am getting ready to come out but I haven’t yet”
“So do you do this a lot? the cross dressing, I mean”
“tried it last week for the first time” he tossed the blanket aside becoming more at ease. “I feel right in this form”
“well then Za__ err what is your name when you are in panties?”
“Zoe I call myself Zoe”
“cute name, listen Zoe finish getting dressed and come out to me and we will talk. I think you will find me a good person to talk with.”
“okay, I would like that”
“good, I will pour more wine and we will share information” I closed the door and went to the kitchen and took out a bottle of champagne I had left from New Years Eve and poured two flutes.
I heard the door open and he came into the room dressed in a tight black dress that came to her knees, with black stockings and a platinum chain around her neck with a matching bracelet. She stood before me and awaited my thoughts.
“well... what do you think”
“I think Zoe” I patted the couch next to me to invite her to sit. “that you are very attractive, that dress shows off your cute little ass.” She smiled as I handed her her glass.
As she sipped she crossed her leg then put one arm over the back of the sofa giving her the look of having b cup tits.
“you know Zoe, if you are worried about what your Mom will think do not be.”
“why do you say that”
“I know she is verrry tolerant of same sex lifestyles.” I turned to face her. “In fact I myself am bi-sexual.” She looked shocked and curious at the same time. “and yes your Mother knows. In fact she has watched while I have indulged in having been inside another man.”
“wow really”
“cross my heart Zoe” I began running my finger over her bare arm. “In fact she has even joined in on occasion allowing me to have a her and a man at the same time”
“that is awesome, has she ever been with a woman?”
“yes”
“when?”
“on her honeymoon with your Father, it was his wedding present he wanted to watch her with another woman. So they picked up a woman in a bar and brought her back to their hotel.”
“I did not know that”
“how could you, its not like it would come up in conversation. How is your Kraft Dinner, by the way I ate another woman’s pussy to please your Father.”
“true”
“so do have a lover Zoe?”
“not really a friend with oral privileges, I swallow he does not” She uncrossed her legs and sat straight on the couch as I slid over and began running my hand up her smooth silky leg. “ he ah he.... he does not want to do anal, s s soo I just come in his mouth” He looked me in the eye knowing I was turned on by him. “What about Mom?”
“well Zoe” I kissed her neck. “she is not here, if she was I wold be fucking her brains out by now, leaving you to jerk off in your room.” I slid up her skirt and pulled down the front of those hot red panties, gripping his cut seven inches. “but she is stuck in Montreal and we are here and I am soooo fucking horny I thought you would like it if we were lovers tonight.”
“lovers? you mean real lovers, you inside me lovers”
I gripped his cock and rubbed it to its full size. “you can say no, or we can have a lovely evening together.” Wet my lips and kissed her as she spread her legs for me. “You ever had a man inside your asshole Zoe”
“no”
“fuck I love virgin ass” I leaned over and took her into my mouth slowly licking and taking all of her into my mouth balls deep.
“oh shit that feels sooooo amazing. I feel so excited”
Before I could stop to tell him to calm down he filled my mouth with his sticky sweet come. Clearly the thought of us together was sending her into major excitement.
“I love your climax in my throat Zoe” I swallowed it all down and licked my lips as I stood up and took off my pants and stripped off my shirt. I pulled her up to her feet and kissed her hard as she gripped my dick and massaged it to its full eight inches. She sunk to a crouch and deep throated me with ease and enthusiasm.
“nice technique Zoe, just wonderful” She looked up at me and smiled as I took her hands and pulled her up to her feet.
I walked her to the big picture window the one that led to the balcony. It was winter so the door was closed but from my loft on the sixth floor the city sparkled in the night below us.
Pushing her chest into the glass I began kissing her neck and pushing a hand over the bra and rubbing as I let my hard on rub between her legs.
“Zoe”
“yes” She put her forehead to the glass as I spread her legs and ripped the red panties off her.
“be gentle I have never been done like this before”
I had brought out of my room a tube of lube and applied generous amounts to myself and then massaged in a lot to her starfish even pushing two fingers in and getting her relaxed as I continued kissing and nibbling her neck.
“ready lover” I whispered. She quickly nodded in agreement as I slowly slid my throbbing cock into her unbelievably tight anus. She let out a gentle moan as the tip passed into her and I began sinking into her all the way to my nuts. I left my dick all the way in for a minute or two as he adjusted to the feel and began by putting her hands and forehead flat on the cool glass and pushed her hips out taking me deeper into her.
“well sexy how does it feel?” I whispered in her her.
“God it feels so good, I love iitah”
“good, now the fun begins” I put my hands over hers and began by pushing my hips in so she rubbed against the glass then as I pulled back and about half way out her hips sprang back too. I slowly fucked her there against the glass as she moaned and encouraged me to speed up.
I stepped back and pulled her out so she was bent over quite far at the hips but her hands were still on the glass and put my hands on her hips and began quickly slamming into her and pulling everything but the tip out then pushing fully into her again.
“I think I am going to come again” she gasped. So I spun her around to her feet again and knelt down and took her into my mouth and bobbed, jerked and sucked her hard and fast and was rewarded with another come filled mouth.
“you taste so sweet babe” I said as I swallowed it all and stood up and kissed her again.
“ I think you need a happy ending lover” she smiled at me.
“indeed” I pushed her back to the dinning room table and pushed her hips onto it and spread her legs wide and slid my aching for relief dick into her and held her shoulders down as I fucked her slow and hard, making her feel each thrust.
“oh fuck Zoe, fuck I am so fucking ready to blow”
“then do it! fill mme up stud, let me feel your release inside my used up asshole”
I stood up straight and grabbed her sides for a couple more hard deep thrusts and let go an epic blast that nearly caused my legs to buckle.
Standing there breathless she sat up and wrapped her legs around me and put hands on my hips as we kissed and caught our breath.
“well Zoe I guess it would be nice if you slept in my bed tonight” I realized she was still pretty much dressed. So I told her to go put on something comfy to sleep in and come slip into my king sized bed with the silky smooth sheets. She smiled kissed me again and sauntered off to the bedroom. I was already naked so I stayed that way and crawled into bed thinking that Annie was a very tolerant woman but how would she accept me screwing her son.
Zoe came into the room wearing a deep purple silk camisole and white boy shorts that looked like silk too. She gave me a little twirl and snuggled in beside me.
“You look hot in that Zoe”
“I love the feel of silk next to my skin. Especially my cock. Turns me on”
She turned on her side and I immediately felt her hard cock against my thigh.
“MMM young men, they are always hard.”
“yes I am and you know what?”
“what?” I said knowing what he wanted.
He turned me over onto my stomach pushing my legs together and rolled over on top of me, his knees on the outside of my legs.
“I bet I don’t even need lube for you do I?”
I just shook my head no as he slid his rock hard cock inside my butt. She slid it in quick and pushed down on my lower back as she began screwing me fast and furious.
“I just love this” she cried as she reached forward and began pulling up on my shoulders really giving me a good thorough dicking.
Then for the third time that night she came.
Before collapsing beside me she kissed between my shoulders. I rolled onto my side and she spooned in behind me.
I fell asleep thinking I had him/her to myself for at least one more day and I liked the thought of that.
It had been a night filled with surprise and hot sex with Zoe the night before. I awoke late on Saturday laying on my side looking out the window of the loft at the snow beginning to fall when the bathroom door opened and Zoe came sauntering out still wearing her purple camisole and white boy shorts. Her long thin blond hair fell around her face as she slid into bed behind me and put an arm over my hip.
“good mornin’ Zoe” I reached back and squeezed her ass.
“Good morning mister man” she slid her hand down and began stroking my naked cock. “I feel like a morning screw” she began kissing my shoulder blades. I soon felt her hard cock rubbing into my ass crack.
“Oh my I have let the genie out of the bottle haven’t I” I breathed as she gripped my hardening cock and began pumping it. She repositioned slightly putting the tip right at my back door. Slowly she slid into my ready ass. Slowly going deep into me as she jerked me off.
“fuck Zoe you are so good to awake to”
“all I want to do is fuck now” She whispered as she quickened her pace with growing excitement. “you have shown me the ways of anal and I love it” I could tell by her breathing that I was about to have my ass filled again. “oh fuck, oh fuck I love this fe-he-hee-ling” she gag as she filled my ass with her first load of the day.
She rolled me onto my back and slid down the bed and wrapped her pretty mouth around my dick and began a rather enthusiastic hummer as she got up on her knees. She slurped and bobbed and licked as I gripped her hair keeping it out of her face as she brought me closer and closer to orgasm. I gripped her hair tighter and and began thrusting into her mouth. Trying to hold out wanting to last longer but her hot wet mouth was driving me over the edge.
I gurgled and tensed as I filled her mouth with morning desire. After relaxing my grip and hips and she swallowed and cleaned me off. She wrapped an arm and leg over me and nuzzled into my side.
I played with her golden hair until we felt like moving. I kissed her head and told her to go take a shower and get ready to go out. I was going to buy her breakfast. As she got up and walked towards the shower she turned to me “you mean as Zakk right? not Zoe?”
“Zoe” I said walking over to her and stroking her cheek. “I want to take Zoe to breakfast as a thank you for last night.”
“but I have never gone out as..”
“today’s the day the world meets Zoe” I said as I kissed her cheek. “when people ask, you are my fiancee’s daughter and we tell the rest of the story the way it really is. She was suppose to be with us this weekend but got snowed in in Montreal.”
She smiled and went and took a shower. When she was done I took a shower of my own as she dressed.
After I got dressed I went to the window as the weather was still holding at a light snow but the sky was about to open up. No way was my fiancee getting home this weekend. I heard her door open and her footsteps behind me. I turned to see her standing there, her hair up in a pony tail and a modest amount of make-up showing off her delicate features. She wore a grey sweater over a black turtleneck with a black pleated skirt with two tones of grey stripes running diagonal on the dress with red tights underneath.
“I hope this looks okay, I still don’t have many clothes yet” she said shyly.
“my dear you look cute. very cute.” I smiled at her. “do you have winter clothes?”
“no never gone out like this.”
I grabbed her ass and we enjoyed a deep, wet tongue in mouth kiss. “Okay come over here” I said leading her to the closet where Annie kept some stuff for when she visited. “ I think your Ma wouldn’t mind you wearing her stuff to keep warm.” I shifted some hangers and found her winter boots that looked like riding boots and told her to put them on as I pulled out a long blue wool coat and she put it on and buttoned it up. It had black fur on the cuffs, neck and bottom. I finished her off with a knit demin blue hat with a pom pom on top with matching gloves. She checked herself out in the full length mirror in the hallway. She giggled as she twirled checking herself out.
We went to a diner down the street and had a long slow breakfast as we chatted and tried to see if anyone could figure out she was in drag. No one gave her a second look. Over breakfast we made a list of the things a new girl should have. She did not have most of the list so after I paid for breakfast I decided to take her shopping.
But not before a cute waiter in the restaurant began flirting with her and gave her his number which she put into her phone with a little wink. I played the protective father and pulled her out of the joint as we giggled and walked away. Then for the rest of our outing I played the loving father taking his step daughter shopping.
Our first stop was a lingerie store where she got five new pairs of panties and bras. They were mostly bikini briefs and boy shorts and the bras were demi cups of satin, lace and synthetics. She promised a fashion show when we got home.
We then went to a clothing store where I paid for three new outfits and her own winter clothes and boots. She had decided as she shopped that Zoe’s look should be casual, cute and flirty. She went for tights, jeans and long sleeve shirts.
As we walked home she spotted a second hand clothing store and she pulled me in. I had my hands full of bags and the weather had picked up. The snow was falling faster and harder. She promised it would be the last stop.
She picked out a couple more sweaters, a mini skirt, a purple bikini and a pair if knee length black pvc boots. Just as we were about to cash out she noticed a manikin at the back of the store wearing a purple steampunk corset. It had light grey floral patterns in raised filigree and grey buttons up the front with small black buckles on the side and one large y shaped leather strap and buckle on the front. It also had leather garter straps attached. She picked out a black lace ankle length skirt and silk fishnet stockings to go with it.
As she waited for the garment to be packaged she whispered in my ear. “when I put that on later I am going to bend over the table and you can fuck me hard and fast.” I got hard just thinking about it. “ consider it a sexy thank you for all you have done for me today."
We got home just as the snow really started to hit. Putting the bags in her room I received a text from Anne asking me to Skype with her. I told her to quickly get back into Zakk for a few minutes as we talked it was very clear that she was stuck in Montreal for the weekend leaving Zakk/Zoe and I to be together. She promised to get home no matter what in two weeks and we would all go someplace nice to eat. No sooner had I closed the lid on the computer than Zoe had reappeared. Under the clothes that she wore to talk to her Mom was the first set of underwear I bought her.
She did a little spin and a strut and came over and kissed me on the cheek and then the lips as I rubbed her ass in the black lace panties. She then went back into the room and changed into the next set of undies. I moved to the chair in the den as it was a big wide comfortable arm chair. She would come out each time show me the 360 degree view then bend over and we would kiss for a minute or two before she changed. She went through all five pair of underwear and the sting bikini which was pink with little white dots. After she kissed me and rubbed my dick loving how hot she was getting me she promised only one more change.
When she returned she had on the corset. She did not have on the skirt instead she had on the black panties I had just bought her with the fishnet stocking being held up by the garters.
“holy shit you are sexy in that fuck me outfit”
“this thing makes me feel so fucking sexy” she purred as she knelt over me and stuck her tongue in my throat. “I just want to get fucked so hard babe. Can you do me like that?”
“gee let me think” I joked as I pulled down the panties and she released my dick from my pants. I pulled her hips forward until her ass was over my swollen member and pushed upwards at the hips as she sat down on me sinking balls deep.
She ran her fingers through my hair as she slowly rode me in the chair. “ah yeh just like that lover make me feel every inch of you as I ride your magnificent cock.” She grabbed the arms of the chair and began a quick deep grind making me feel like I was on cloud nine.
“fill my ass lover” she begged as I pulled the corset down and licked her nipples hard. “please baby come for me, come in my ass.”
Oh shit yes! In your ass for sure you sex maniac!” I growled as I came. Gush after gush onto her hot tight ass.
“thank you for all the sexy under wear I am glad they turn you on” She stood up to go get changed but before she left I slid to the edge of the chair and took her into my mouth. She was rock hard and needed relief from the building fluid in her balls so I sucked her off. Slow and easy as she left her arms to hang on the side and I grabbed her ass pulling her in to my throat.
She came so hard I did not think she would stop. I choked on the volume and had to swallow three times.
I wasn’t expecting much after that. We sat on the couch in the evening watching movies and having munchies. The storm was in full swing and you could not see most of the city for the snow.
Zoe was in a tank top and pair if soccer shorts with her head in my lap as she finished a glass of wine. She stretched out long and I could see a growing erection beginning. I was impressed with her sex drive. Almost envious of it but I was having no problem keeping up. She settled back down and I slid my hand into the shorts and began stroking her with my fingers.
“what cha’ doin’ there Sir” she smiled.
“just jerking you off ma’am’” I gripped her dick and began jerking her off.
She stopped me rolled over and took my dick out again. She started a long slow blow job taking me right down her throat. It was so good I just leaned back against the back of the couch and let my head hang back as she showed off her fellatio skills. To get better angles she got on her knees and pulled my pants off and went back at it bobbing her head furiously as she made me blow a huge load.
After she had cleaned me up and licked her fingers clean she told me to lay on my back on the couch. I did so as she pushed the shorts of and knelt between my legs with one foot on the floor the other on the couch. She slid her rigid dick into me hard and deep. She put my one leg over the back of the couch and left her hand on my knee as she held my other leg in the air and began fucking me hard and fast.
“Hun you are a hot fuck machine” I said as she began riding me even rougher.
“yeah? you like me inside your asshole do you Sir”
“oh yeahs”
“good, now shut up and let me get nasty hungh lover” She rolled me over on my stomach and my head hung over the arm as she told me to keep my ass in the air. She shoved her pole back into me and grabbed my hair as she rough rode me. She slapped my ass and started gasping hard just before she climaxed so hard she collapsed on top of me.
After that we were spent. It had been a while since I had that much sex in one day and for her it was the first time. We retired to my bed where we fell fast asleep.
We had sex three more times the next day. I now had her convinced to live as Zoe. I took her back to her dorm room and helped her unpack all her new clothes and hang them up. She would not let me leave however until she gave me one final hummer to get me home. She was on her hands and knees as she got me off with her cute little mouth. I pulled out just before coming and coated her face and clothes with semen.
She kissed me on the cheek as I left and I grabbed her ass as we promised to hook up again soon.
I can not wait to tell Annie about how I made her son into a girl and so completely happy as a slutty cock whore.