Boss's New Wife

I cleared my throat. "Hi."

"Can you take off tomorrow? My company is doing inventory and they gave us all, the day off."

"Tomorrow? I don't think so..."

"Well ask, ask that boss of yours. You work so friggin' hard." She got mad so quick, I didn't even know what to say. "I'll call him myself."

"No, let me ask, I will call you later."

"I'll call you, I'm going to be busy, I'm going out tonight to the movies with everyone."

"Oh, okay." And she hung up. I was wondering who was everyone. I hadn't taken Lois to the movies or even out to dinner in months. She started going out while I was gone, I always cooked when I was home so she went out to dinner more. She was becoming very popular with her friends.

I didn't like disappointing her, since I was away from her at the beginning of every week she got a little more independent. She got a little more self-assured, even more confident. She also started asking more questions. Where did I stay those two nights, why couldn't I sleep at home, and why do I smell like strange perfume and aftershave lotion.

I closed my eyes and shook, I had to get back into the correct headspace. I had to become his little girl again. I opened my eyes slowly, I stood in front of the mirror playing with my long hair, admiring my arms. Crossdressers always noticed the little things, the arms, the ankles, the look you put on when you are just playing with your hair or thinking or surprised. The little giggle when you are happy or excited, were the things that I truly relished. My favorite little moments. When I am home with Lois I never had moments like these, ever.

***

"Honey! Are you ready!" I heard Scott call me.

I walked down the stairs in my pink top and denim skirt, my clutch in my hand. My yellow heels clicking down the stairs, I got his attention and he met me near the bottom step. He grabbed me around the waist, he was the same size as me while I perched one step above him.

"Hi," I said, I was trying to be cute.

"Hi, you look great. I love those lips." He kissed me as I put my arms around his neck. "Maybe I should let you dress yourself more often."

"Well, I am a big girl now."

He kissed me again. His hand crept up to my breasts, under the tank. "You are. Very big."

We went out the front door, he held my hand, I was still nervous. Once the late afternoon sun reached my eyes I got a little jittery, I got a little tense, I still was uncomfortable being out in a skirt. I didn't mind being in the safety of the vehicle but outside made me nervous. I had to warm up to it. He took me in the garage and we hopped in his Jeep.

We went to the park. We backed into a quiet spot. He was looking out the front window, "It's pretty crowded for a Tuesday afternoon."

"Mmm." I swallowed, this spot brought back bad memories.

"I was thinking we should go in the backseat, like when we were teenagers." He looked at me and leered. We had actually done this before. I didn't really mind it, his windows were dark and there was plenty of room.

I smiled and licked my lips, "Okay. You're the boss." He liked when I called him that, but I didn't. I saved it for when I wanted things to be quick.

We moved to the backseat. I felt the slight wind up my skirt, I closed the door quietly I didn't want to draw attention to us. He kissed me as he took me in his arms, we heard and watched the kids on the swings, on the monkey bars. We saw people walking their dogs and carriages. We kissed, it was nice, I wish I had the guts to do this as a teenager. My long nails danced on his belly, I moved down and grabbed his cock through his sweatpants. He changed, this was definitely the plan. He wanted me to have easy access to his hard manhood.

"I know what you like." He always thought all I wanted was his cock, I needed it in my hands, my mouth, my bottom. "I like making you happy and horny."

I played with him through the cotton blend, pushing his cock around as he kissed my lips, my face. He kissed me slowly, he kissed me deliberately. I liked this, it took him so long to figure out what turned me on, what got my motor running. What made my fingers tremble and my lips quiver. At the start, it was all about him and his sexual desires but now I feel it is about the two of us. I loved feeling his tongue move into and around my mouth, I loved that he thought I was beautiful and sexy. He loved showing me off, he wanted the world to see his beautiful sexy wife, one day I will be ready.

He kissed me on the nose, he smiled, he whispered, "Hop up."

I unbuttoned my skirt as he watched. Six metal buttons leading down to my legs, hiding my beige panties and perfect hips. I rubbed my thighs, he slid his hand under my crotch and squeezed, his thumb massaging the front, his fingers getting close to my bottom. I moaned as he rubbed some more, he pressed my crotch with the palm of his hand. I was getting excited, I was slightly tucked, my 'clit' was pointing down and inching toward the back of my panties. I wanted to stay tucked, I wanted to look like a woman, but Scott had other ideas.

I slid on top of him, my legs around him, my breasts in his face, my little 'clit' sticking out of the top of my panties. The first bunch of times he wanted me in public places, it wasn't easy, I was afraid, I didn't want people seeing me. People seeing me being so feminine and on top of a man. Being sexually active with a strong attractive man. What would Lois say if she found out a male wanted me to cum with him? Wanted to cum inside me. Wanted us to orgasm together.

I forgot about her as Scott kissed me and played with my ass in the pantyhose. He loved this, he was so hard. I pushed up his sweatshirt, I wanted to rub against his bare skin, his hard stomach, and chest. His hard body now made me so excited.

A car parked next to us. "Scott, don't move I don't want them to see us."

"Ha, don't worry about that."

A woman got out of the passenger door, she looked right at me, we made eye contact. She watched me as Scott kissed my neck and chest. "Scott, that woman saw me."

"So, can't a man and his wife have sex in the afternoon?" He shook me I was still looking outside, I was nervous again, "Can't they?" I watched the woman tell her friend about the two lovers in the back of the Jeep.

"Mmm-mmm."

I moved up, I closed my eyes, he slid down my pantyhose and panties even more. I pushed my breasts into his face again, he loved this. I felt his cock growing underneath me. His ex had very small boobs, he told me she never wore a bra. He told me he felt like he was with a teenage boy when they were in bed, he would search for her tits and they were non-existent. Even her nipples were small. Now, he couldn't complain, I didn't feel like a boy at all. I felt like a porn star, a supermodel, a wife.

I looked to the right, then the left, at least there were no other people around. We were surrounded by parked cars. I had put a little lube inside of me, just a little before we left, I didn't need a lot anymore. My bottom was so much wider than when we first started having sex. My 'pussy' has grown accustomed to his large cock.

My doctor was the first one to notice it. He asked me when did I start getting more sexually adventurous, I begged him not to say anything to Lois. He shook his head and told me to be careful, he wrote something in his notes.

I felt Scott's cock push in, I felt just the head of his large dick, he never had trouble gaining entry, ever. "Ohh slower baby," I told him. He was always so rough to start, but I needed him to be gentle I needed him to take his time at first. He started inching inside of me, he was so big and I felt him opening me up again. We started all over every Tuesday, my body had to meld to his, I had to become his wife all over again.

"Look at me."

He loved watching me as he fucked me, he loved the idea that he was the first man to give me an orgasm. He loved to think his eyes, his smile made me excited. He especially loved that I could take his whole entire cock inside of me. I was sitting on his lap, his manhood completely hidden. Once he was completely inside I would moan, I wanted him to know I was enjoying it, enjoying him filling me up, it used to be an act. I moved slowly, I rotated my bottom, feeling him against my body, feeling his cock press against my insides.

"Mmm, I love your cock inside me, baby." I would bite my lip, my voice getting extra high. "Oh, you feel so good." I would talk to him quietly then kiss his cheek, his nose, his lips. I had to look at him, he loved looking in my eyes, my blue eyes. He loved watching the little movements and twitches on my face as he plowed slowly into me. I never got hard from him fucking me but I always came, I always had an orgasm and he knew it. He knew I loved this, he knew Tanya trained me well, she made me lust after his cock in my body. There were suddenly people outside and I knew they heard us moan, they saw the Jeep shake. They all knew something was going on inside the deep blue truck. I was hoping they didn't look too close.

"God you have the bluest eyes, don't you?" He whispered as I shook my head and my whole body once again became a little girl, just for him.

"Ahh, Scott..." I made a little yelp, it was happening, I felt I was ready for an orgasm. This is what made him cum, that was what he loved more than anything. The fucking was secondary to my excitement. I didn't start out a cock slut but I was turning into one and he loved it.

"Take my cock baby, take it. I know what you love." Once again a man was bringing me to orgasm. I screamed, I held on tight. Who would have expected my life to take this road, to need a man to fuck me, to hold me, to look into my eyes?

"Scott, deeper," I begged, "Oh, my God baby, faster, harder... yes..." He smiled, he knew I was forgetting the women making eye contact with me, the sounds of the dogs barking at squirrels, the squeal of swings. I moaned loudly as his cum started to shoot inside me, I could feel the contractions in my bottom as he pushed and came inside me again, he was hugging me and kissing my chest and neck as we came down from our orgasms, I came all over his belly. I knew he couldn't wait to watch me lick him completely clean. He would pet my head and then I would kiss him and share it, all of it. I would then lay worn out, my hair against his cheek.

He whispered in my ear, he had asked me these questions before, I knew all the answers.

"What do you want?"

"Men."

"What makes you excited?"

"Men."

"Who is your favorite man?"

"You, baby, of course." I would kiss him long and hard and then he would let me relax against his body once more.

***

Usually, when Scott took me for rides he had an ulterior motive. Tanya had trained me to suck cock, it wasn't that hard, it wasn't that weird I had things in my mouth before. I had taken pictures with my lips making an O, with my lips primed to accept something long and hard. But other things were more difficult, other things I was barely ready for.

The first time we had tried intercourse together, we were behind the Jeep. He never warned me, he didn't even warn Tanya. I was bent over holding the bumper while the back door was open. I was scared, I was petrified. I wasn't even lubricated. My heels sank into the dirt, my tight skirt pushed up over my waist, the wind on my exposed legs. We were only slightly hidden from others on the beach. He wanted me to scream, he wanted someone to hear me, he wanted me to have an orgasm. None of that happened, I cried, it hurt and I was scared that someone knew who and what I was. I was so afraid someone would look at me and yell out 'tranny,' 'fag,' 'perverts.' Even though my large diamond would be in the view of onlookers. I wanted to scream 'Look I'm a married woman, don't judge me!'

I told him, my voice was so soft, so quiet. "Please Mr. Sanders don't be so mean to me, I will do whatever you want me to do. I promise." I begged him. I didn't understand the power trip he was having, I didn't understand what was happening inside his brain. He used to be so nice to me at work, I was one of his best employees. He zipped up his pants and made me get back in the Jeep. He was disappointed, he hit the steering wheel, he grumbled. We never attempted something like that ever again. Never intentionally outside in front of people.

We got home and he called Tanya to complain about me, complain about my training. But she yelled right back at him over the phone. She yelled for ten minutes straight. I heard her voice through the tiny speaker. He paced the house listening to her, shrugging his shoulders, shaking his head, while he was watching me. I was on the couch, my legs under me, my mascara was a mess. I was hoping he wasn't going to hit me.

She asked him how he could expect his virgin girlfriend to be able to take his eight-inch cock the first time. She wasn't ready. What was the matter with him, didn't he ever sleep with a virgin before? She asked him, and he never did, I was the first. The thought of it made him very happy, made him even more excited, he was so much nicer to me after that. His blonde, feminine virgin.

Flowers were delivered the next day. To me and then Tanya. Mine said 'With Love from Scott.'

I went back to Tanya's, she laughed about it, but I was still so sore. He barely even got the head of his cock inside of me. She made me put vaseline on myself. Two weeks later things would be so different, she had to move things along, come up with a new plan. She would make Scott let me get used to his cock, he had to take it slow. He would have to put KY on himself and inside my 'pussy.' It would take a while, it would be worth it.

Soon when I was ready, he started to cum like crazy. I would make him cum the entire time I was with him. I would learn to cum myself much later.

***

"Do you even like men?"

"Um, I think so." I didn't know, did I? Did I have to? Tanya wanted to know. I liked when I was dressed up looking like a woman and getting admiring glances from men. I was usually in my car wearing sunglasses. I was usually hyperventilating and rushing to get back home or hidden in the dark office.

"Scott expects you to enjoy your time together."

"I will."

"Well, you better."

We went shopping, I was all dressed up. She made me find a masculine scent that I liked, something that would remind me only of him. Something completely different. We went to one of the big department stores and looked for cologne, aftershave, deodorant. I took three different aftershaves and a bunch of other things back to her house.

She gave me a laptop and started a slide show of pictures of Mr. Sanders, Scott. She put aftershave on a towel. She then lubed up my backside. I had a mirror in front and next to me.

"Do we really have to do this?" I asked. She didn't answer me, she shook her head, what did I know. She put something inside me. I screamed.

"Stop being a little sissy." Whatever she had it slipped in hard, I felt like I was being split into two halves. "It's just a vibrating butt plug. No big deal, it's not even that big." She held her two fingers close together, it felt tremendous.

I moaned, it felt too big for my tiny hole. For the next hour, the plug started to vibrate whenever a picture of Mr. Sanders appeared on the screen. I started to like it, it felt okay. It stopped when it showed landscapes and gardens. Tanya then introduced a 'Magic Massage Vibrator' to my 'clit.' I had to hold it, it kept on falling. It was such a big device. She started to show more suggestive shots of Mr. S. I could smell the aftershave, he was smiling at me from the screen, inviting me to orgasm with him. He was so handsome, he was so muscular and strong, I liked his eyes, I think. The vibrator was making me excited, the butt plug was making me over-excited. I didn't know what to do. I was starting to get just a little hard and soon I was starting to cum. She would make me say his name over and over again as I shot my sperm all over the towel, she would make me scream, soon she would make me need it. I would start to enjoy it much later.

The next week she took away the butt plug, later that day she took away the massager. I had to cum without either of those things, I had to cum from the look and feel of a man. I even had to practice at home that coming week. When I came back the next Monday she made me try again, I couldn't do it. I wanted to so bad, but I just couldn't cum. I felt funny, a little weird, I still felt embarrassed, even her knowing a man was making me slightly aroused. I was stimulated but I couldn't get over the cliff to orgasm. I couldn't make the jump to having a man take me over that edge, no matter how much I was enjoying myself. Scott was going to be even more disappointed with me.

Tanya and I had a light dinner, we had some wine, we watched a movie. She made me get dressed for bed. I was in front of my mirror wearing a white pushup bra, lacey white panties, and white sheer thigh highs. I had on four-inch white pumps, I looked like the perfect virgin. I had on my long blonde wig and perfect makeup. My lips looked incredible, plump, pink, and titillating. I wasn't dressed for sleeping I was dressed for sex. She took a couple of pictures of me, she made me pose, she made me give her sensual looks.

Tanya made me get on all fours on the bed, she put on soft music, she set up the laptop in front of me. Soon pictures of Mr. Sanders appeared on the screen again, then pictures of hard cocks, hard men's chests, more pictures of Mr. S.

"I'm going to go to bed, have fun." She was gone, I was alone in my lingerie. The smell of my Chanel floating around. The scent of sex. I could see my lips behind the laptop, could see my ass bounce in the mirror. I watched the screen, I watched him smile at me, I heard a noise. The music still played, someone was in the room with me.

"Tanya?" I whispered. I felt hands on my hips, I froze it wasn't Tanya, it wasn't a woman. These were huge strong men's hands. I smelled Scott's new aftershave, it was turning me on. I was starting to enjoy the scent mixing with my perfume. I looked up, I could only see his hairy, naked chest in the mirror, it was dark, the only light coming from the laptop, it wasn't Mr. Sanders behind me. I felt something hard against my ass. I felt a cool liquid being put inside me as I watched the montage of pictures and pricks on the screen. I felt something enter me. "Ahh... Oh my god." It was long and hard. It stopped. I felt it go deeper, it was harder, it was deeper. The disembodied hands rubbed my ass and back, slid down to my stockings. I heard a man breathe, I heard his slight moan. He took my hips in his hands and pulled me closer, no... I was being taken away from Mr. Sanders, his eyes, his chest, his smile, I wanted him closer, I wanted to feel his breath on me. The laptop was too far away, I wanted him to kiss me, to whisper in my ear.

"Ooh." I heard the man behind me, his cock now completely lost in my bottom, my ready and willing 'pussy.' He pulled me in and then he pushed me out, I felt his body against me, it felt great, there was no pain I was enjoying this. We started to fuck. He did all the work, he manipulated my body, back and forth and then I started to get into it, I caught the rhythm. I kept on returning to his body, his cock hitting the air and them buried deep and hidden.

"Oh Scott you feel so good inside me," I told his picture as it came up, "I love that I can make you so hard, Uhh," I told the back of his head, the back of his naked body, his legs, the pictures of his cock. I wanted him to look at me again, I wanted him to approve of my wantonness and my hanging breasts. I felt the cock ramping up speed, I started to scream. The man was grunting, he was enjoying my ass, he was so stimulated, his hands once again roaming my soft fragrant body. I felt his cum shoot inside me. a close-up picture of Scott finally appeared on my screen inches from my face, too far away to kiss, to lick. "Ahh... Scott..." I came. I came all over the bed. I closed my eyes, I felt like I couldn't stop.