Babysitting Ch. 02

It had been a nervous couple of weeks since Tony had caught me dressed in his wife's clothes, which had led to us having sex together. I wasn't sure if Tony would be angry or upset with me or worse still, if he would tell people about me being a crossdresser. My fear's faded slightly when Jan asked me to babysit the following Friday night.

Friday night arrived and i got to Jan and Tony's house for 7.30. Jan invited me in and i stepped through the door into the hallway, Tony was standing there, he smiled and said hello, relief filled my body. As i walked to the living room, Jan went upstairs to get her jacket, Tony followed me and asked if i was okay. Nervously i nodded, asking if all was well between us, Tony smiled and said everything was fine, then handed me a piece of paper, telling me to read it after Jan and himself went out.

Jan came back, she let me know that Lucy was asleep and explained where they were going if there was any problems, then they both left. I watched them drive off then took the piece of paper out of my pocket. Any worries that i might of had quickly disappeared as i read the note. Tony had written down what he wanted me to wear and asked me to put on makeup. The note also said that he would find a reason to leave early and that he would be back around 10pm. I almost screamed out, trembling with excitement as i anticipated the evening ahead.

Just after 9pm i went and checked on Lucy, she was sound asleep. Walking into Jan and Tony's bedroom i could feel the butterflies in my stomach. I opened Jan's underwear drawer and, as per Tony's note, picked out a pair of black stockings and black lace knickers. Next i found a black lace corset with suspenders, also in the note, before going to the wardrobe. Tony wanted me to wear a particular dress, it was dark red and almost see through, it had a lace flower pattern and long sleeves, very sexy.

I quickly stripped off my clothes and eagerly started to dress in the sexy feminine clothing, excited that i was getting dressed to please a guy. The corset felt incredible against my skin, i gasped with delight at the feeling of the straps over my shoulders. Slowly i slipped each stocking up my legs, savouring every second, before connecting them to the suspenders. I couldn't stop smiling to myself as i pulled the knickers up, taking a long, deep breath as every inch of my body tingled.

I walked around the bedroom for a minute or so, enjoying how the underwear made me feel. I picked up the dress and pulled it on, it was very tight and hugged my body nicely. Smoothing it out and pulling it down over my legs and adjusting the sleeves felt so good, so feminine, so right. It covered my shoulders but wasn't tight around my neck, finishing half way between my thighs and my knees. I took a deep breath then turned to look at myself in the full length mirror. A huge smile spread across my face as i stared at my reflection, loving what i was seeing. You could see my underwear through the dress, adding to the excitement building up inside me.

After a few minutes i went over to Jan's makeup table and sat down. I chose a dark pink eye shadow, it really made my eyes stand out. Applying black eye liner and thick mascara next then darkening my eyebrows before choosing a bright red lipstick. My hair was short and dark, so i gave myself a parting as i brushed my hair over to one side in a kind of tomboyish style. Tony wanted me to wear a pair of high heels, Jan had loads to choose from, i picked a pair of 4inch black heels and slipped them on. I felt incredible, i loved looking at the woman staring back at me from the full length mirror. I picked out a perfume and applied a little, the scent was lovely and made me feel very feminine.

I went downstairs to wait for Tony, my stomach full of butterflies and my mind racing, unsure of what to expect. The dress felt amazing, and i loved the feeling of my stockings touching together as i walked around. Finally i sat on the edge of the armchair, nervous and shaking and breathing heavily. Just after 10pm i heard the front door open, my whole body started to tremble and a thousand thoughts went through my mind, i prayed that i wasn't making a mistake and that it was Tony coming through the door.

A few seconds later relief flooded my body as Tony walked into the living room. He stood still and looked at me and started to smile. I made eye contact with him, but was unable to say anything, my mouth suddenly dry. Tony put his hands on his hips and started nodding his head, then told me to stand up. Shakily i got to my feet, suddenly feeling vulnerable and very nervous as i turned to face him. I was told to turn around a couple of times so that Tony could have a good look at the clothes i was wearing, then he told me to walk around so that he could watch me walking in the high heels.

As i strutted around the room, the trembling subsided and i felt myself relax. Tony told me that i looked sexy and i blushed, i shyly thanked him, hearing those words excited me, and all my fears suddenly disappeared. I put a hand on my hip as i faced him, trying to be as feminine as possible, and i asked Tony if i was wearing the right clothes and if i looked anything like he was expecting. Tony walked up to me and stopped, i suddenly felt very small as i looked up at him, he told me that i looked perfect, that i was wearing the right clothes.

Tony gently touched my face as he said how pretty i looked in makeup, complimenting my hair, my breathing became very heavy. Tony leaned forward and gently kissed my lips, i didn't resist. He pulled away and started to take his jacket off, he said that he liked that i was wearing perfume, again i was lost for words and just smiled. The thought that i was turning Tony on made me feel incredible, i knew that i wanted to please him, that i was his for the taking.

Tony asked me to go and get a bottle of wine and some glasses while he put on some music. I returned to the living room, the main light was dimmed low and music was playing but the volume was turned down. I joined Tony on the sofa and he poured the wine, we clinked glasses and both took a drink. I was sat on the edge of the sofa and Tony was sitting back, he kept giving me compliments on how i looked, telling me how feminine and sexy the clothes and makeup made me look.

My mind was racing and i felt the need to please Tony. After a few minutes he told me to go and get a towel from upstairs, when i returned i noticed a small tube of cream on the sofa and i smiled, knowing that it was going to be used as lube at some point. Tony took the towel from me, then stood up and got very close to me, again i felt timid and small as i looked up at him. Tony put a hand on my shoulder and pulled me to him, an involuntary squeal left my mouth and i instinctively put my hands on Tony's chest. Nothing was said as he leaned down and kissed my lips.

I responded immediately and returned the kiss, opening my mouth and inviting his tongue to dominate mine. Tony pulled away, my lipstick smeared across his smiling lips, and stared at me. He knew that i was his, he knew that i wouldn't resist him, that i would obey his every command. I moved my hand down to his trousers, his rock hard cock was bulging and bursting to be released. Without being told, i pulled his zip down, i smiled up at him, and slid my hand inside his trousers. Tony gasped as i touched his long cock, his helmet felt huge and swollen. The excitement of knowing that i was the reason he was so turned on blew my mind.

I couldn't resist any longer and dropped to my knees, hungrily unbuttoning his trousers and pulling them down along with his underwear. Tony's cock was impressive, thick and long, his large helmet shiny and tight and oozing. I stared at it for a moment then looked up at Tony and smiled, almost pleading with him to let me suck him, but i didn't need to plead, i knew what he wanted me to do. Taking him in my hand i felt him throb, pre cum oozing out of the tip. I gently started to stroke his length, moving my mouth closer, i smiled up at Tony and kissed his swollen helmet, pre cum sticking to my lips.

Taking him into my willing mouth i slowly started to suck and tease, Tony's breathing became heavy as he gasped and panted, he called me a good girl as he put a hand on my head. Those words thrilled me as i took more and more of Tony's cock, filling my mouth with as much of him as i could. As i worked up a rhythm, bobbing my head back and forth, i soaked his manhood with my spit, choking occasionally as he slid down my throat. Tony removed his shirt as i continued to suck him, then he put his hands on my head again, before telling me how sexy i looked once more.

After a few minutes Tony told me to stand up, as i got to my feet he stepped out of his trousers. He made me turn my back to him and walk a few steps away, then ordered me to take my knickers off slowly. I lifted my dress exposing my lacey knickers, i moved my hips and ran my hands over my backside, giving Tony a little show. He liked what i was doing, calling me a naughty girl as he stroked himself. Bending slightly forward, i slowly pushed my knickers down until my arse was on show. I looked behind me and asked Tony if he liked what he saw, then i gripped each cheek and showed him my tight hole.

Tony quickly stepped forward and got on his knees, pushing my legs apart and pulling my knickers down to my knees. Seconds later Tony put his hands on my arse and started kissing and licking both cheeks, i almost squealed with delight. I put my hands on my knees and closed my eyes, enjoying the sensations flooding my body. Tony used his thumbs to open my cheeks, exposing my tight hole, i held my breath as i felt his finger gently touch it. Tony leaned forward, opening my cheeks wider, then licked my pussy, the sensation of Tony's tongue on my hole felt incredible. I let out little moans of pleasure each time his warm tongue touched me, loving every sensual move.

After a few minutes Tony stopped and got up, telling me to stay where i was. Moments later he was standing beside me, his rock hard cock inches from my face. He told me to stay bent over and to give him a blow job, i willingly turned my head and took his throbbing helmet into my mouth. I sucked on his swollen helmet, swirling my tongue all over the tip, making his cock throb and ooze. Tony stroked my arse again, calling me a good girl, then he opened the tube of cream, and i felt his fingers slip between my cheeks.

I continued to suck as Tony smeared my hole with the cream, making me quiver with every touch. He started to push his finger against my pussy, applying pressure until his finger entered me. I gasped as i pulled my mouth from Tony's manhood, he quickly put his other hand on my head to prevent me standing upright, shushing me as he did so. In a hushed voice Tony reassured me, telling me everything was okay, calling me his sexy girl. seconds later, Tony started to finger me, the feeling was intense as he started to build up a rhythm.

One finger became two as my pussy was worked and stretched, my legs almost buckling as wave after wave of pleasure flooded my body. Minutes passed and eventually Tony stopped fingering me. He laid down on the floor and told me to step out of my knickers, i did as i was told before Tony growled at me to suck his cock some more. Kneeling between his legs and taking Tony into my mouth, i started to suck and stroke him. Tony kept encouraging me, calling me a naughty girl and telling me how sexy it looked watching me suck him. A while later i gripped his manhood and looked up at Tony, and asked him to fuck me, saying that i wanted him inside me. A huge smile spread across his face, then he told me to straddle him.

I pulled my dress up to my waist and placed a knee either side of Tony's hips, straddling him. Reaching behind me i guided his helmet to my pussy, then slowly lowered myself down. Tony's helmet penetrated me and i gasped in air pausing for a moment, Tony tensed and a low groan left his mouth. Gradually i took more and more of his thick cock until he was all the way inside me. I stayed still, panting and gasping, waiting for the pain of being stretched to ease before carrying on. With my hands on Tony's chest, i looked down at him and smiled, then slowly started to raise myself up, then back down. Tony stroked my stockings as i rocked back and forth, the groans of pleasure coming from both of us.

Tony felt huge inside me and it wasn't long before i cried out as my body shuddered, a strange new sensation deep inside me. Tony asked if i was okay as i panted heavily, i whispered a yes and nodded as the feeling subsided. I told Tony that i didn't know what happened, saying that it felt like i had had an orgasm deep inside me, he called me a good girl again and i started to move my hips once more. I moved my hands behind me and positioned my feet so that i could lift myself up and down, then started to fuck Tony's cock. Tony had to guide himself back into me occasionally as i got carried away, enjoying fucking myself with his thick manhood.

After a while i was told to stop and Tony pushed himself up from under me. He was breathing heavy and i got the sense that he was very worked up sexually. Tony pulled me to my feet and guided me towards the dining table and told me to face him, my body was tingling and i felt feeble and submissive as Tony stood naked in front of me. Tony put a hand on my shoulder and pushed me back, at the same time he lifted my leg until i was laying on my back on the table. Very quickly Tony entered my aching pussy, my legs in the air as he pulled me onto him. As he gripped my stocking clad legs he began pumping me hard and fast, uncontrollable groans forced out of me, Tony growled at me, urging me to be quieter. I understood why and i bit my lip, gasping with pleasure with every thrust.

Tony stroked and bit my stockings, pumping me hard as i layed back on the table. A few minutes later he pulled out of me and forcibly turned me over on to my stomach, feeble squeals left my mouth as i was manhandled into the right position. Tony plunged straight back into me and continued to pump me hard. I was almost on tip toe as Tony gripped my dress, pulling me back onto him as he pushed into me, the sound of our skin slapping together was intoxicating. I looked over my shoulder at Tony, a huge smile was on his face as he called me a bitch and a dirty girl, i respond by telling him to fuck me hard, to make me a woman.

The pounding continued until suddenly Tony withdrew again, grabbing me and pushing me to my knees. He guided his wet, sticky cock to my mouth and told me to suck him, i straight away did as i was told and took him in my willing mouth. I could taste our sex on his slippery length as i sucked, then happily bobbed my head back and forth as Tony talked to me, calling me a dirty girl and telling me how sexy it was watching me suck him. It wasn't long before i was told to get up again and go to the sofa and lay on my back. My body was trembling and my pussy ached pleasantly as i did as i was told.

As i laid on my back i watched Tony stroking his manhood as he approached me. He knelt down on the sofa and looked at me, then growled at me to spread my legs. I opened my legs wide, breathing heavy as i anticipate what was going to happen. I had one leg in the air against the sofa and my other leg i opened as wide as possible, then Tony leaned forward between my thighs, he stared at me for a moment, then kissed me, i responded instantly, returning the kiss, our tongues fighting for control as the kissing became passionate.

My eyes snapped open and i inhaled deeply through my nose as Tony penetrated me, without breaking the kiss. I groaned and closed my eyes, reached around Tony's head and body with my arms and pulled him close to me. Tony began to grind and pump into me as i laid under him, eventually the kissing stopped, and Tony buried his face into my neck and shoulder, then started biting and kissing me as moans of pleasure left his mouth. I whispered in his ear, encouraging him to fuck me and telling him to cum inside me as the pumping became more intense. I wrapped my stocking clad legs around Tony's waist, digging my nails into his back as i wiggled my hips in time with his thrusts.

Tony's whole body tensed and i held him tightly, sensing how close to cumming he was. He raised his head and our eyes fixed on each other, as he thrust hard and deep into my pussy, before Tony exploded, shooting load after load of thick, warm cum into me. Tony expelled air through gritted teeth as i growled at him to fill me up, and with every hard thrust, he did. Tony collapsed on top of me, gasping for air, his body giving little trembles as he started to untense, relaxing his muscles. I whispered a thank you to him several times as i cuddled him, and listened to him panting for air.

A few moments later Tony slowly withdrew from my aching pussy and sat up on the sofa. I stayed still, my left leg now on his lap, as Tony started telling me how wonderful i was, saying how tight i felt on his cock. He stroked my stockinged leg and said how sexy i was in his wife's underwear, and how feminine i looked in makeup, i couldn't stop smiling as i heard this. I let him know that i really enjoyed getting dressed up and putting on makeup for him, that i would be more than happy to do it again, Tony looked at me and smiled, then told me that i should go and sort myself out and reapply my lipstick.

After doing as i was told, and putting my knickers back on, i went and checked on Lucy before heading back to the living room, Tony had poured me another drink and i sat down next to him. Not much was said for a while as we drank our wine, Tony run his hand over my stockings and over my dress occasionally. Gradually the conversation built up and we started to talk about the events of the evening, Tony paid me lots of compliments on how i looked etc, and i felt myself blush as i thanked him.

Tony stopped talking and stared at me, then he told me to stand up and take my dress off. I get to my feet and faced Tony, and slowly started to lift my dress, pulling it up and over my head before dropping it on the sofa. I stood with my hands on my hips, then turned to face Tony, i smiled as i watched his eyes scan my body, enjoying the sight of me standing there in his wife's corset and stockings. I walked around in front of him, hoping to excite him, wanting to arouse him. Tony opened his legs and almost growled at me to give him a blow job.

I willingly knelt down between his legs, his cock already rock hard as i took him in my hand. I began stroking him as i looked him in the eyes, moving my mouth closer to his throbbing length. Tony called me a sexy bitch as my warm lips enveloped his helmet. I could taste our sex again, as my tongue licked and teased Tony's sticky shaft, the taste excited me as i began to bob my head. Tony started to describe in detail the way he had fucked me earlier, how he had cum inside me, telling me that i was a naughty girl and that i deserved to be fucked. I continued to suck him, eagerly wanting him to explode again, to shoot his load down my throat.

The talking became less and less and Tony's breathing got heavier, then he suddenly yelled at me to stop, quickly he stood up and grabbed my arm, telling me to get to my feet. Tony pushed me round the back of the sofa and roughly bent me over. My knickers were pushed down to my knees and i felt the tip of Tony's cock slip between my cheeks. Tony paused as he told me how cute and sexy i looked wearing his wife's underwear, then, without warning, he plunged his full length into my pussy. I gasped loudly almost uncontrollably as Tony again, growled at me to be quieter. I bit my lip closed my eyes as he began to pump me hard and fast.

Tony's hands roughly stroked my corset and again he told me how sexy i looked in his wife's underwear. My whole body shuddered as the fucking got even harder and faster. I looked over my shoulder at Tony and, through gritted teeth, i begged him to fill me up. I felt Tony stiffen slightly then, as he let out a deep groan, he grasped my hips hard and began to shoot his thick, warm cum deep inside me. He trembled with each ejaculation, my stretched pussy aching with every throb of Tony's thick cock. He held himself inside me for a minute or so before he withdrew slowly. I was told to stay where i was as he walked back round the sofa and picked up his drink.