Pajama Gram

By Andi

Published on Feb 12, 2010

Transgender

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Author's Note:The following is purely fiction and the property of the author. Any feed back would be greatly appreciated.

I hope everyone has a wonderful, romantic and sex filled Valentines Day!!!!!

PAJAMA GRAM

It was Saturday Morning and I was trying to catch up on my sleep when I heard the door bell. By the time I came awake and looked out my second story window to see who was there the UPS driver was pulling out of my driveway.

I laid there but was unable to go back to sleep so I got out of bed and went to the kitchen to make some coffee. When I opened the door to get the paper I almost tripped over a package that was laying on my porch. I picked it up and seen that it was suppose to be delivered to my neighbors house. I carried it inside figuring I would run it over to their house as soon as I got dressed.

I was drinking my coffee when I noticed where the package was sent from. It was a delivery from Pajamagram.com. Since it was February 13, the day before Valentine's Day, it did not take a genius to know it was probably lingerie meant for my neighbor's wife.

My neighbors are Jennifer and Blake Hunter. Jennifer is a very pretty blonde girl. She is around 5'5", 110 pounds, long hair and very blue eyes and a very perky set of tits.

As I thought about what kind of sexy lingerie Blake had sent to Jennifer, and what it would look like on her hot body, I felt my small cock starting to stir. It had been a long time since I had been with a woman and masturbating can only relive so much tension.

I just had to see what her lingerie looked like. I turned the package over and over and realized that if I was careful I could open it from the bottom and tape it back without anyone noticing.

My hands were shaking as I carefully opened the package. Oh my it was a very sexy lacy white teddy with red hearts and it had garters and red stockings. It was beautiful and I knew that Jennifer would look very hot wearing it.

I felt the familiar urge starting to shoot through my body. I wanted to put the teddy on very badly.

At this point I have to tell you that I have been wearing bra, panties, lingerie and even skirts and dresses since I was 16 and started using my Mom's panties to Jack off into.

As I ran my hand over the lacy material it occurred to me that no one knew I had the package. I did not have to sign for it and if my neighbors reported that they did not receive the delivery and the UPS driver came back searching for the package, all I had to do was claim ignorance.

I took the teddy upstairs and laid it on the bed. I took a quick shower. I dried my body and checked out my nude figure in the mirror. I was only a couple of inches taller than Jennifer. Probably less than 20 pounds heavier. Since I was a computer programmer and worked from my home I had let my blonde hair grow out. I had very little body hair and since it was blonde it was almost unnoticeable. I know I would never look as hot as Jennifer but with a little work I could look some what sexy, and at least I would feel pretty and feminine.

I felt my excitement grow as I stepped into the teddy and felt the garters brush against my thighs. Shivers went through my body as I sat on the edge of the bed and rolled the stockings up my legs and attached them to the garters.

I brushed my hair out and stood in front of the mirror admiring how I looked wearing the lingerie. Except that I was flat chested I thought I made a cute girl.

As I looked at myself in the mirror my left hand came up to rub my nipples through the material of the teddy while my right hand went down to rub my small cock, which at times like this I thought of as my clit.

I started pinching my hard nipples and rubbing myself harder. My knees were getting weak so I made my way to the bed and laid down. Old fantasies started coming to mind as I stroked and rubbed my Clit. Visions of faceless men with hard cocks, being made to suck some while other men forced me to all fours so they could fuck me.

It did not take long until a powerful orgasm hit me and I came all over my hand. I put my hand to my mouth and savored the taste of my own cum. I laid there feeling great and drifting in and out of consciousness. My cock was still rock hard and I had started stroking it again.

The doorbell was rang again. Damn it! Maybe if I ignored it they would go away. The doorbell gave way to someone banging on my front door.

"Stan, open up, I know you are in there I seen you get the paper this morning. I am not leaving until you open this door."

It was Blake.

Unsure of what to do, but knowing that I had no choice but to see what he wanted. I quickly put on a pair of pajama pants, tennis shoes and my robe, tying it tight against my body. I went down stairs and after taking a few deep breathes I open the door a crack.

Without much effort Blake barreled his way into my house. While his wife is a small gorgeous blonde, Blake is a very tall, very well built Blackman.

He stood before me. "I have been waiting for a delivery all morning and it has not come to my house, I was looking out when I seen you get the paper and trip over something, was it the thing that was meant for me?"

I stammered out, "wha..what are you talking about?"

"I seen you trip over a package left on your door step, was it delivered here by mistake?"

Thinking quickly, "Oh no that was something for work, it was some parts I needed to upgrade my computer system.."

He seem to relax, "Sorry I really hope that package comes today, it is for my wife, we have not been getting along to good lately and I need to score some points with her so I bought her a special present for Valentines Day."

I was beginning to feel sorry that I had stolen her gift. I was starting to fidget so to cover up my nervousness I offered Blake a cup of coffee of something else to drink. He said if it was no trouble he would love a beer.

Thinking every thing was going to be ok I let Blake follow me to the kitchen. That is when things went bad. I noticed the box on the table a split second before Blake seen it.

I tried to grab it and hide the logo but Blake was quicker. Looking at the box then glaring at me, "So it was computer parts huh? Why does it have my wife's name on it?"

I was not sure how to answer so I just looked away. Blake reached out and grabbed me by the arm. When he turned me to face him my robe came undone and he just stared at the red and white top of the teddy I was wearing.

"WHAT THE HELL? Are you wearing my wife's teddy?"

"Uh...please I am so sorry. I will repay you for the present."

Blake just stared at me for what seemed like hours, but I am sure was just a minute or so.

Finally he spoke, "I knew you were not that manly but I had not idea that you were such a sissy. Take off your robe and pants now, I want to see what I paid so much for."

When I hesitated he grabbed my arm and bent it behind my back, "I said take it off now. You don't want me to undress you myself do you?"

I was shaking in fear as I took the robe off and let it drop to the floor. I kicked off my tennis shoes and his expression changed when he seen my stocking clad feet. As I pulled down my pajama pants exposing the garters and stockings Blake actually started to smile.

"Turn around I want to see the whole outfit." I slowly started doing a 360 turn. When I faced Blake again he was laughing. I started crying.

Blake surprised me, he reached out and brushed a strand of hair from my eyes. "Why are you crying?"

"You are laughing at me."

"I am sorry Stan...Wait I can't call you Stan when you are dressed this pretty, do you have a feminine name you prefer?"

"Yes Sir, I go by Sara."

"Well Sara, I was not laughing at you, I just thought it was odd how good you look in lingerie. While I am sure that it would look better on Jennifer, I think it looks pretty good on you."

I smiled at that and He commented on my pretty smile. Blake took a beer from the refrigerator and guzzled it without taking a breath. We were still looking at each other, I was not sure what to do and started fidgeting.

Blake took another beer from the fridge and then took my hand and pulled me back into the living room. He sat on the couch and pulled me down beside him.

He opened a beer and handed it to me, then opened a second one for himself. Without thinking about it I crossed my legs like a woman would do.

"So Sara, I can tell by your mannerisms that this is not the first time you have worn lingerie, how long have you been playing dress up?"

I blushed but the beer was calming my nerves somewhat, I stared at the floor, "Uh since I was 16 years old."

"Do you have a boyfriend Sara?"

"No Sir, you are the first man who has ever seen me dressed."

"Am I the first person to see you dressed up?"

"Well yes and no, I did wear a pair of panties for a girl in High school but when she seen them she threatened to have me beat up and then tell everyone at school if I ever tried to talk to her again. You are the first person to see me in more than just panties."

Blake took what was left of my beer and sat it on the coffee table. When I looked up at him he was smiling. I was still looking into those dark eyes when I felt his arm around my shoulders pulling me to him.

I felt him gently kiss my lips as he placed a hand on my thigh. I was afraid to move, one part of me did not want this to happen, but the other half felt like I had been waiting for that kiss all my life. I was confused so I did nothing.

Blake must have taken the fact that I did not pull away or resist as a sign and he kissed me again. Harder this time and when I felt his tongue press against my lips I opened then letting him explore my mouth. I had never experienced a kiss from the female point of view but I have to tell you, Blake really knew how to kiss.

I felt myself melting into his arms. One hand was rubbing up and down my back as the other was working circles on my bare thigh, I felt Blake's hand slide up to briefly brush against my cock. By this point it was throbbing.

I was gasping when Blake finally broke the kiss. Blake just sat there and stared at me like he was either trying to make up his mind or rationalize what had just happened.

Blake took my hand and kissed it. "Sara, I am a married man, but like I said we are having trouble. I caught her cheating with one of my friends." He sighed, "I still love my wife dearly but its been a while for us and you are turning me on so much right now."

I was flattered and realized that at that moment Blake could have done anything he wanted to me or with me. It was my turn to make a move, I leaned in and gave him a brief kiss. " I have never been this far before with a guy except in my fantasies. You are a very handsome, very attractive man. Please...." I let that please hang in the air as I started kissing Blake again.

He seem to be battling with his conscious but when I squeezed the bulge of his cock he seemed to make a decision. Oh my it did feel big. I continued to kiss him as I unsnapped his pants, then unzipped them. I broke the kiss and slide to my knees in front of him.

I took a deep breath, I could not believe I was actually going to do this but I was to far into it to stop now. Blake lifted his hips allowing me to pull down his pants. It was the moment of truth and I leaned down to kiss Blake's cock through his boxer shorts.

I grabbed the waistband of his boxers and pull them down. Oh My God, his cock was huge. It had to be 8 1/2, maybe even 9 inches long and thick. I smiled up at Blake right before I took the head into my mouth and sucked it as I started working my right hand up and down the shaft.

I was savoring the taste of his pre cum as I started squeezing his balls. I pulled back and then I bent down and sucked one then the other ball into my mouth. Eventually I started slicking the length of his cock from the balls to the tip.

I heard Blake gasp as I tried to take the entire length into my mouth. At about 6 inches I started to gag so I backed off and let the cock slip from my mouth. I took another deep breath and tried it again. I went slower and tried to relax my throat. I after several tries I was finally able to take 8 inches, not quite all of it but I think Blake was enjoying what I was doing because he had started moaning.

He was running his hand through my hair. I felt incredibly sexy and feminine, on my knees, with a big hard cock in my mouth. I started wondering why I had not found a way to do this before. I was varying the speed at which I was bobbing my head up and down Blake's cock. Some times I would work my mouth up and down his cock fast then I would stop and take it nice and slow.

Soon Blake put his hand behind my head and forced my mouth down as far as he could. I realized what was about to happen and tried to pull my mouth off of his cock but He held my head in place and started shooting his cum into my mouth and throat.

I had no choice but try to swallow as much cum as I could. Still some escaped the corners of my mouth. Apparently Blake was not exaggerating when he said it had been a while since he had been with Jennifer because it seemed like he came gallons.

Blake held me there until his cock started to go soft then he let go and I was able to let his cock slip from my mouth. even soft, Blake's cock was still impressive. it was long black and shiny.

It seemed natural to bend back down and lick up the left over cum seeping from his cock head. Black reached down and grabbed my arm pulling me back onto the couch. He surprised me by kissing me again. I felt so relaxed and happy that I leaned my head against his chest and let my breathing return to normal.

Blake broke my daydreaming when he asked, "Are you sure you have never done that before?"

"No that was my first time."

"Wow, you are a natural you are better than most women I know." That made me smile.

"Uh I am really sorry I opened Jennifer's present. I just could not help myself."

"That's ok Sweetie, I also got her a very expensive bracelet. I may go to Victoria's Secret later and pick her up something sexy. Besides a sexy girl like you deserve pretty gifts too."

I melted into his arms as he kissed me again, a slow passionate deep kiss.

All good things have to end and Blake got off the couch and started dressing. God he was a handsome man. He really was not sure how to make his exit and I thought it was cute as I walked him to the door and gave him another kiss good bye.

I wanted to ask if maybe we could do it again some time but I was afraid he would say no. I decided to leave it open and hope that at some point he would visit me again.

I watched Blake leave then I went back up stairs and laid on the bed. I started stroking my small cock as I relived the event of the morning. Before I knew it my hand was covered in cum again. I licked it from my hand, more slowly this time savoring every drop, it was not as good as Blake's cum tasted, but it was nice and flavorful.

After I came I was suddenly very tired again so I pulled the covers up and drifted off to very peaceful sleep. _________________________________________________________________________

When I awoke it was late afternoon. At first I was disoriented, wow what a vivid dream I had. Then I noticed what I was wearing and I realized it was not a dream. I had actually given my neighbor a blow job.

Knowing I could turn on some one like Blake made me feel sexy and special. Since I did not have any plans for the night I decided Sara deserved to be pampered.

I went down stairs and watched some TV, letting my excitement grow before I started. Around 6 I could not resist any longer and went upstairs. I turned on the stereo to something soft and classical. While the tub was filling up I lit some scented candles.

I added a light scented bubble bath, a mixture of vanilla and jasmine, to the tub and then climbed in. I let my body soak in the warm fragrant water. I took my time and washed my hair. When I emerged from the tub I felt fresh and clean. I wrapped my hair in a town and then wrapped another towel around my body.

After I blow dried and brushed out my hair, I sat on the bed and painted my toe nails a bright pink. Then I painted my fingernails to match my toenails. When my nails were dried, I went to my special drawer, the one where I kept all of feminine lingerie. I did not have a huge collection but I did have several nice things.

I decided on the pink lacy boy shorts and matching pink lace bra. I had cum twice already that day but when I slide the shorts up my legs I felt my "clit" start to get hard again. I hooked the bra and turned it around and slid the straps up my shoulders.

I rummaged around and found two old pair of pantyhose that I used to stuff the bra, giving me t illusion of having a set of perky 34B breasts. I did not have any makeup but I did have a tube of bright pink lipstick that matched the bra and panties I was wearing. I only had two pairs of women's shoes and I picked the black 3 inch open toed heels so I could admire my painted toenails.

I realized I was hungry so I slipped on a short silk Kimono I had picked up on a trip to San Francisco and headed for the kitchen. I felt so feminine walking down the stairs in my high heels.

First thin I did when I went down stairs was to close every blind and lock all the doors so I would have privacy.

After fixing a salad and opening a bottle of wine I sat at the table and ate my meal. It was easy to imagine I was all dressed up and out on a date at a fancy restaurant with a handsome man. The image that kept coming to mind was Blake.

When I was done eating I took my glass and the bottle of wine to the living room and decided to watch Pretty Woman, a standard "chick flick".

Halfway through the movie I was almost finished with my third glass of wine when someone rang the door bell. I froze, I knew whoever it was could hear the TV but there was no way I could answer the door dressed like I was.

"Stan, it's me Blake, answer the door. Please."

After what we had done earlier today there was no reason to be shy now. I quickly opened the door and let him in. Blake carried with him a brown bag. He stopped dead in his tracks. I started to pulled my kimono tight around me as I watched his eyes go from my face down my body and back up again.

"Don't Sara, you are even more beautiful than you were this morning. Pink is definitely your color."

Blushing I whispered. "Thank you."

"Oh, I brought you a six pack to replace the beer I drank earlier."

"You did not have to do that but since you did, do you want one?"

Blake laughed as he said, "I thought you would never ask."

I was conscious of my heels clicking on the tile as I walked to the kitchen and I was pretty sure I could feel Blake's eyes staring at my ass as i walked away.

I got put the six pack in the refrigerator and got out two cold ones and a glass. I poured on beer into the glass and carried the other one with me as I returned to the living room.

Blake was seated on the couch So I handed him the glass and sat the bottle on to the coffee table.

"You are not having one?" he asked.

"No I am drinking wine tonight", holding up my half empty glass. I sat on the couch and tucked my legs under my butt letting my robe fall open.

Blake seemed to like looking at me. To be honest it was an incredible turn on to be looked at as a woman and Blake was not just looking, I thought I could see lust in his eyes as they kept roaming up and down my body.

He asked me what I was watching and I told him.

Blake laughed, "That is one of Jennifer's favorite Movies. She says it reminds her of us."

I gave him a questioning look, "Oh really?"

"Yes, but she was not a hooker when we met, I met her at a strip club, she was a dancer. The headliner actually and she was very good." He laughed again, "I got her attention when I stuffed a $100 bill in her g string. I went back every night for a week until she agreed to go out with me."

I sense a sadness in his voice as he talked about her. So I let him talk.

"She is out with her friends at a bachelorette party tonight. One of her girlfriends is getting married tomorrow. Can you imagine that, getting married on Valentines Day? Anyway we got into a big fight right before she left. I did not want to be alone so I came over here. I hope that is ok."

I felt sorry for the guy, "Sure its Ok you are welcome here any time."

With that he leaned close and kissed me. "Oh Sara you are a nice person and you are so very pretty." He kissed me again.

As he kissed me this time his hand came up to my right breast and squeezed it. I was not sure if he realized he was squeezing padding or not.

I pulled away and he looked disappointed.

"Blake, I want to ask you something. Are you sure you want to do this? I do not want you waking up tomorrow with regrets and I do not want to cause problems with you and Jennifer."

"Sara this has nothing to do with Jennifer and believe Me I want this very bad, I want you and I want you RIGHT NOW!!! But not here, not a quickie on the couch, lets go get comfortable on your bed."

I took his hand and lead him upstairs. As soon as we entered the bedroom Blake took me into his arms. This time when he kissed me it was a deep passionate and aggressive kiss. One hand went back to my breasts while the other went behind me to squeeze my ass.

he slide my robe off of my shoulders as he started kissing my neck. Without warning he pushed me down onto the bed and stepped back. I watched him intensely as he undressed. I had already become intimate with his gorgeous cock but when he took off his shirt and bared that magnificent chest I squealed with delight. Blake was a stud. I licked my lips as he took off his shorts.

My new black lover laid beside me on the bed and his hands started to slowly explore my body. I was running my hands up and down his back as he started cupping my ass pulling my hips to him.

He surprised me by rolling onto his back and pulling me on top of him. Our tongues twisted around each other as he continued to squeeze and play with my ass. His hands on my butt caused my small panty clad cock to rub against Blake's big hard cock.

Blake started to thrust his hips up like he was fucking me and the friction was just to much and my body started to spasm filling my panties full of sticky cum. He held me tight until my body relaxed. I lay there with my head on his muscular chest while I tried to get my breathing under control. I was in a post orgasmic daze when Blake rolled me over onto my back.

He put his hands under my thighs and forced my legs into the air. He slide my panties to the side. He licked a finger and then pushed it into my ass. MMMM that felt good. I had used a vibrator in my butt before but it felt nothing like this.

Blake continued to finger my ass when he added a second then a third finger. The three fingers working in and out of my ass was stretching me, getting me ready for Blake's huge cock. Blake spit into his hand and used that to lube up his dick.

Blake smiled down at me, "Are you ready sweetheart?"

All I could do was just nod. He kissed me one more time then he lined his cock up with my anal opening and pushed forward. He was gentle and went slow but when the head of his cock pushed past my anal ring it hurt tremendously and I was having second thoughts.

Blake stopped to let me get use to the head of his cock. Half of me wanted to screm at him to stop and the other half wanted to feel Blake slamming his cock in and out of me. Instead of protesting all I could do was groan in pain.

He started working his cock in and out slowly. The pain was incredibly but deep down this was what I wanted and I was determined to see it through. Blake grunted and thrust forward, I knew he was in me all the way because I felt pubic hair brush against my butt.

I closed my eyes and concentrated on blocking out the pain. Blake started fucking me in earnest. He was slamming his cock into me and started to pick up speed. It started as a slow burn that spread though out my body. Soon the burn turned to a tingle then to pleasure.

I started moaning with pleasure and lust. It was incredible. I felt ever nerve in my body burning with desire. When I opened my eyes, Blake was giving me such an intense look of lust that it scared me. He was grunting when he slammed into me and groaning when he pulled back and he was breathing very hard.

"Oh God Sara I am so close...so fucking close. Damn you are so hot and tight. OH GOD I'M GOING TO CUM!!!!!!!!!!" And with that he pushed forward and flooded my ass with his juices then, he collapsed on top of me.

Blake's cock eventually started to soften and slipped from my ass. He rolled off of me and lay there panting. We shared a brief kiss then I started kissing and licking my way down Blake's body. When I got to his cock I started to lick around the base, licking up any cum that had been left behind.

I started licking the length of his cock and it started getting hard again. I took the head into my mouth and sucked it before I started working my mouth up and down the shaft. His cock had an earthy tangy taste to it.

I sucked for several minutes before it was rock hard again. I looked up to see a satisfied smile on Blake's face as I took as much of his cock in my mouth and throat as I could. I was sure that with enough practice I could deep throat his entire cock.

As I sucked I also started to squeeze his balls. It seemed like I sucked his cock for an hour but I was rewarded for my effort when He came in my mouth a second time.

I crawled back up and Blake took me into his hands and we cuddled for a while but he eventually had to get dressed and go home. I walked him to the door and right before he kissed me one last time and said "Happy Valentine's." _________________________________________________________________________

I had hoped that maybe Blake would start coming by often but I did not hear from him until two weeks later when I got a phone call. When I answered the phone Blake told me that he wanted to see Sara again because he needed to talk to her. I told him to give me 20 minutes to get ready.

I dressed in the red and white lingerie he had bought for his wife and was waiting anxiously when he showed up.

He told me he had something he needed to tell me. The corporation that he worked for had offered him a promotion and a transfer. He had talked it over with Jennifer and they decided to try and make a new start in New York.

He seen I was upset and he took me into his arms. We had sex one last time but it was nothing like the Valentine's day weekend. He bent me over the back of the couch and fucked me. It was a quickie and there was no romance and very little passion. when he came Blake zipped up and left without a word.

I never seen nor heard from him again. There will always be a special place in my heart for Blake. He made me a woman and he showed me that I loved cock.

I am sure it will not be long until Sara has a new boyfriend, or maybe she will just be a slut with lots of admirers and visitors. Either way I was changed forever.

THE END

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