The Restart Pt. 02

Around 6 am, I felt someone nudge me. Becky was standing by my bed. "Hey there, can I get a ride home? I will be forever grateful" she kind of giggled.

I nodded and said "I am in my boxers, if you want to look you can, if not you can go out in the living room."

Becky replied "Go ahead Chris, I've seen quite a bit over the years."

I got out of bed, Becky looked at me and said "Damn, you do work out as much as I thought" I reached down and grabbed my sweats and a sweatshirt, Becky continued "You have awesome legs, do you shave them? I mean you could pass as a female leg model." I just shook my head and she giggled, I think she was still drunk.

She put her head down and said "Chris, Can I just wear your stuff home? please? " I nodded and I grabbed her a bag for her Halloween outfit. She put her clothes in there and we left for her house.

Her house was on the outskirts of town, in a more rural area. I dropped her off and she kissed me on the cheek. "Thank you for everything, you are truly a good guy for taking care of me. I owe you."

I did some chores that day, watched football and took a nap. Sunday I woke up early, worked out, showered and made lunch. Around 2 pm, my phone rang. It was Becky.

"I'll buy you Wings and beer, if you meet me for the Steeler game. Think of it as a tribute to you for taking care of me. Or even better, I will pick you up for it."

Relieved that she didn't notice any cum stains in her pantyhose and panties from Friday night, I answered "Absolutely, we can. What time?" Becky said she would come by at 3:30. I changed and waited.

I enjoyed Becky, she was very outgoing, very forthright and funny. She wasn't afraid to voice something. There was something about her as well that oozes sex appeal. But with her being my co-worker I knew I would have to not pursue anything.

Around 3:30, I heard a knock on the door. Becky walked in with a bag of my shorts and t-shirt. "Here you go sport." Becky was dressed in a white Steeler long sleeve shirt, Dark blue jeans, and white slide on sketchers (with no heel). I glanced again, and saw she had tan nylons under her jeans.

We drove to BWs and sat at the bar. We ordered some beers, and started watching the game making small talk. After the first beer, she looked at me and said "What's your story?" "Do you date?" I gave her my story, the break up and just looking to establish a career. I looked at her and said "yours?"

Becky replied "Married young, had some issues with cheating, explored some other options and finally decided I was sick of him. We are both alphas, so that was an issue as well."

I looked at her and apologized for asking. She replied "It's all good, we did some swinging with a couple from out of town a few times, the final straw for us was when the other wife and I thought our husbands were golfing and we caught her husband sucking my ex's cock in the steam room of the golf course."

My jaw dropped, Becky smiled "It's all good, I have tons of experience sweetie." as she winked at me.

We watched more of the game and had 2 more beers. I got up to use the bathroom and one of her canvas skechers slid off her foot onto the floor. I reached down and grabbed and stared at her sexy nylon covered foot. She had on bright red nail polish on her toes. I went to give it to her and she said "Put it on Chris, you are already down there." I grabbed her nylon covered ankle and slid her shoe back on. My cock was straining in my underwear and I went to the bathroom to regain my composure.

I used the bathroom and came back. Becky smiled as I sat down and asked me "Everything good?" I nodded and she smiled. I sat down and she was sitting on the bar stool now with her left leg folded under her right leg which was hanging down. Her shoe was off on her left leg, revealing her nylon covered sole right next to me. I glanced down a few times at her foot.

Becky motioned with her finger to me to bring my ear to her mouth. She sensually whispered "I knew you were a nylon perv. I noticed it at work, and how you always look at my feet first to see if I am wearing nylons. Right now you can't concentrate on anything but my nylon covered foot 2 feet from you, can you?" I began to blush and she continued "I wear them because they are good support and make my legs look good, plus I have noticed a few nylon pervs out there. You are the first one I find appealing."

I was completely caught off guard. She said "I should probably take you home, before it gets too late"

Becky paid the bill, put her shoe on and we headed back to my apartment. We arrived and she turned the car off and said "I'll walk to your door." We got to the top of the stairs, I entered the code to get in and she pinned me up against the wall of my apartment. She aggressively kissed me and soon I moved her to the couch. We slipped off our shoes and I quickly unbuttoned her jeans and slid them off. She had on sheer to waist pantyhose with no panties on.

We kissed and I began to rub her pussy through her pantyhose. She broke our kiss and whispered, "rip my pantyhose Chris and lick my pussy." I put my fingers along the seam of her gusset and ripped a hole. My cock was rock hard and slipped off my jeans after ripping her pantyhose open. I dove down to her pussy and licked the edges before exploring her clit with my tongue. I was good at performing oral and soon she began to moan and soon pulled my head away as she orgasmed.

I was rock hard and she had me sit on the couch, she knelt in between my legs and began to suck and stroke my cock. I was enjoying my blowjob when she told me to lay down on the floor. I laid down and she moved her nylon covered legs and feet towards my head. She moved her foot to my face and began to jerk my cock. I began to lick the sole of her foot and she moved her foot on my face as she gave me a handjob. She sensed I was close, and she put her mouth over the top of my shaft as she stroked me. I exploded and came into her mouth, she didn't miss a drop and swallowed. She maneuvered herself for her lips to meet mine and gave me a kiss. I could taste cum as she transferred some of my cum into my mouth. My cock twitched at the sensuality she had.

She got up and slid her jeans back on. "I should get going, we should meet on occasion, this is fun and hot. I will see you at work tomorrow." She slid on her shoes and left.

I chilled out for the night.

That week, I didn't know what to do. How serious was Becky about hanging out? I was a little embarrassed about her figuring out my nylon fetish, so I was trying to be less obvious with it. Plus I still enjoyed dressing and blowing Justin.

Everything came to a full circle on Friday. Thursday night, I worked out and came home and showered. I logged on to Yahoo that night and there was a message from Justin. "Would love to meet for lunch again tomorrow, at the same place and same time as last time. Let me know if you can."

I replied back "I should be able to, same attire as last time?"

I waited and there was no response.

I went to sleep and woke up the next morning, I checked my messenger and Justin replied "Yes and I do have a surprise for you."

On Friday, if you paid $5 towards a charity, you could wear jeans. I decided I would wear them. I showered and shaved my legs. I slid on a pair of black pantyhose, pink panties and a shaper. Over it I wore jeans, a black long sleeve shirt, black ankle socks and my slide on ankle boots.

I went to work and once again was extra cautious. Around 11:50, I let the receptionist know I was leaving for lunch and went to the property that I met Justin at before. He was there in his SUV. I followed him to the same abandoned Radio Studio. He handed me a bag.

"There is a enema in there, and lube in case I want to fuck you today, plus something I think you will look hot in."

I walked to the bathroom and stripped down to my lingerie. I did a quick enema and then put lube on the entrance of my ass. I opened the bag and in it was a Maids costume. It was pink with black trim. I slid it on and looked in the mirror. I looked hot, if I only had make up and a wig.

I walked out to the studio. Justin's jaw dropped as I jumped on the table and crossed my legs. He walked over and slid down his jeans and underwear. His hands roamed my pantyhose covered legs and ass. He pulled me off the table and pushed me down to my knees. I knelt on the dusty floor on my black nylon covered knees. He moved his cock to my mouth and I sucked it sensually. I felt so feminine in the maids outfit. I was turned on by the fact he wanted to see me in it.

He was rock hard and pulled me up. He ripped my panties right off my ass and I was there in my pantyhose. I stopped him and said "I have to go back to work, so don't rip my pantyhose, I will be too horny to be commando"

He rolled down my pantyhose to the top of my knees and had me bend over with my chest and face on the desk. He pulled my skirt up on my maids outfit. He spread my legs open and I felt the tip of his cock at the entrance of my sissy pussy. I heard breath deeply as he entered my sissy pussy with his cock. He began to thrust and ravaged me ass hard. He smacked my ass and told me how hot it was.

Within 4 minutes Justin's cock twitched in my ass, and I could feel him cumming. He must have not cum in a while because when finally pulled out, cum began to drip down my thigh onto my pantyhose. He handed me a napkin and I tried to pad my ass with his enormous amount of cum dripping out.

I slid up my pantyhose finally and walked to the bathroom to change.

Justin followed me in and said "Sorry about your panties, you can keep the maids outfit to wear. I can't wait to see you again. "

I thanked him, dressed back up and headed back to the office.

I tried to focus on work, I was really horny, my cock was leaking precum and Justin's cum was becoming sticky on pantyhose legs and there was some that dripped out of my ass into the gusset of my pantyhose.

I work until 4:30 usually. Around 4:15 Becky came into my office.

"Wow Chris, I didn't expect you to be wearing jeans today. Good for you. I decided to dress up today."

Becky was wearing a black/white checked skirt, a black turtleneck, tan pantyhose with black ankle boots. She looked absolutely smoking hot. She always did.

I looked at her and said "You did, you look awesome."

She came over and said "A few of us are going to Gibby's for a beer after. I think it would be in your best interest to come there."

I hesitated and said "I need to run home quickly, I forgot to take my heartburn pill."

Becky smiled and said, "I will follow you there and park my car there instead of downtown, if that is okay?"

I replied, "Of course." All I thought about was how I had to beat her to my place so I could peel off my cum stained pantyhose. At 4:30 I logged out and hopped in my car. I headed to my Apartment and ran upstairs to change before Becky got there.

I slipped off my shoes and went to my bedroom. I slid my jeans off and my shirt. I took my socks off and began to slide off my shaper. My cock was semi hard and I wished I had time to jerk off quickly, but with Becky coming I knew I wouldn't.

I walked over and put my shirt on a hanger and put my shaper away when I heard Becky's voice. "This is something I didn't expect to see, I was going to ask to use your bathroom." I forgot to lock my door when I came in.

My heart sank, I was standing in black pantyhose with cum stains all over the ass and legs. I was caught and mortified. Becky was standing at the door to my bedroom, looking sexy as hell. She took off her boots at the door, her sexy toes were painted red and looked sexy under the reinforced toes of her pantyhose.

I mumbled back to her. "I can explain, it's not what you think. Please don't say anything.' I was babbling and in pure panic mode.

Becky walked over to me and whispered to me. "It all makes sense, the shaved legs, you always looking at my feet etc. The only thing I want to know is why you wore pantyhose to work and whose cum is on the ass of your pantyhose? If you come clean and open, this secret is ours. Just like our hookups."

I was completely screwed. Would Becky tell my co-workers? I would have to find a new job and move. I was pissed at myself.

Becky knelt down on the floor of my bedroom, right by me, she reached up and slid down my pantyhose. She put her mouth around my cock and sucked my cock and fondled my balls. I became rock hard in a second. I was in ecstasy and she stopped.

"Tell me what this is all about, and I will let you cum in my mouth. First of all "How long have you dressed in women's lingerie?"

I answered. She said "What got you into dressing?" I told her the story about my girlfriend's pantyhose in my waste basket.

She would stroke my cock after each answer. "Whose cum is on your ass and how often do you hook up with guys?" I opened up and answered her again, told her about Justin etc.

She said "One final question, What started you hooking up with guys and do you always dress?"

I told her about my boss at work, my carelessness and what happened. How I stopped for a while etc.

Becky looked up at me and said "I really appreciate your honesty, it will be our secret as long as you are honest with me." She then went back to giving me a blowjob. I was so horny with my day, being in pantyhose and how sexy she was, that I blew my load in less than 2 minutes. She kept all the cum in her mouth and stood up and french kissed me.

"You better change and we should get going," Becky said as she went into my bathroom. I changed into male underwear and she put her boots on. We headed to the bar. Becky only stayed for a drink and got a ride to her car at my place. I stayed for 3 and headed home. I went to bed and tried to keep my mind from wandering. Becky seemed out of sorts when she left.

I thought of calling her on Saturday but declined. I had an easy day on Saturday, watched some college football, cleaned etc. Sunday Morning I went for a walk and came back on the answering machine with a message from Becky. "Hey there, I was seeing if you wanted to come over and watch football. Let me know.

I called her back and told her I would come over and bring something. I felt more at ease that she was inviting me over. I got ready, stopped at the store and headed over there.

I arrived over there, Becky had on a yellow Pittsburgh Steeler shirt, a denim skirt and tan pantyhose. She gave me a hug and grabbed me a beer. We chatted about football and watched the game. At halftime I got up and used the bathroom. Becky was in the kitchen and said. "I have something to show you, let's go to the bedroom."

I walked in and on the bed was a pair of red silk pajama shorts and top, and a pair of black thigh high stockings. Becky looked at me and said "Can you put these on for me?"

I blushed, but nodded. I stripped down naked and slid on the sexy pajamas, I slid the thigh high nylons up my legs and my cock was semi hard again.

Becky nodded with approval and motioned me to follow her to her vanity. She told me to sit. She put some foundation on her fingers and spread it on my cheeks. She then put some mascara on my eyelashes and eyeliner as well. She brushed some blush on my face and finally put lipstick on my lips.

She stepped away and smiled. "You would be a hot bitch if I got the chance to prepare you." I looked in the mirror and was in awe of how feminine I looked, even without a wig. She pulled me up and kissed me passionately. She stripped her skirt off and she had on thigh high stockings with no panties.

"Lick my pussy Chris, or what do you want your girly name to be?" I replied, "Chrissy works."

Becky laid down and I crawled between her legs. Her pussy was shaved and clean, and I went down and licked her clit and fingered her pussy at the same time. She moaned and said "You are so good at this, It's amazing." Within 5 minutes, she began to breathe heavily and her hips bucked. She orgasmed intensely for almost a minute. She sat up and said "Take your bottoms off, slut." I slid off the bottoms of the pajamas and sat on her bed in the silk top and black thigh high stockings.

"I want you to jerk off for me Chrissy, look in the mirror at how pretty you are. Cum for me Chrissy." She moved her sexy nylon covered foot to my balls and rubbed the smooth nylon along my groin. I reached down and stroked my cock. Once again I didn't last long and ropes of cum landed on Beckys foot. She brought her foot to my mouth and I licked my cum off of it.

Becky told me to put the bottoms back on, and we watched the rest of the football game in her bedroom. I licked her out one more time and headed home for the night.