My soon to be wife, Annie, had taken a job out of town and I only saw her every two weeks or so. She was scheduled for a flight home on Friday night, and I was going to pick up her son Zakk from his dorm so 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 last and he had let his hair grow long; it was thin, golden blonde, and 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 a girlfriend good bye, so 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 without her and she would fly in tomorrow. So 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 he asked for wine instead–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 clouds and darkness rolling in. I feared the storm that had 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 homework. 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, seeing there was a showing of an old Bond movie at a local cinema and thought a guys night out might be in order. I folded 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 stepson: 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 makeup 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?”
“Uhm 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 so we can 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 Year’s Eve and poured two flutes.
I heard the door open and she 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 and that the 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.”
“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?”
“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? It’s 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.”
“So do have a lover, Zoe?”
“Not really, but 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…so 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.” I wet my lips and kissed her as she spread her legs for me. “You ever had a man inside your asshole, Zoe?”
“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, 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 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.
“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 brought out of my room a tube of lube and applied generous amounts to myself and then massaged a lot into 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 in 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, then 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 ear.
“God, it feels so good. I love it, ah…”
“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, put my hands back on her hips, and began quickly slamming into her and pulling everything but the tip out, then pushing fully into her.
“I think I am going to come again,” she gasped. So I spun her around to her feet again, knelt down, and took her into my mouth; bobbing, jerking and sucking 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 said as she smiled at me.
“Indeed.” I pushed her back to the dinning room table and pushed her hips onto it, spread her legs wide, and slid my aching-for-relief dick into her, holding 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 me 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, wrapped her legs around me, and put her 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, crawling 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.
“Mmmm, 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. He slid it in quick and pushed down on my lower back as he 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, he came. Before collapsing beside me he kissed between my shoulders. I rolled onto my side and he 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.
(Image Source: Oh Man! Studios)