Pajama Gram

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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

Any feedback would be greatly appreciated.

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14 Comments
marelthegoodgirlmarelthegoodgirlover 1 year ago

I think this could be a very sexy story but sadly I could only get a few paragraphs in before I had seen one too may "I seens" I am not by any means a grammar cop but that one is unforgiveable

AnonymousAnonymousover 3 years ago
Slut

You say slut like it's a bad thing. It's not Tom/Tammy Liked the story a lot thanks

FRSWRITERFRSWRITERabout 9 years ago
very nice

very nice story i love tranny stories

AnonymousAnonymousalmost 11 years ago
Very Good Writing

Loved it Sweetie

AnonymousAnonymousover 11 years ago
fantastic story

This story is one of the best on Literotica. Most similar stories are about fast, forced sex but your story is about a man making love to a CD who wants to feel like a woman and to be treated like one. That's exactly how I feel. I too love cross-dressing and when I do I love sucking cock and getting fucked by my male lovers. Just like in your story, my lovers "make love" to me -- they kiss me passionately, they fuck me gently (I appreciate your realism when you described the 1st time being painful but then later enjoyable -- that's the truth!!!) and my lovers treat me like the woman I am when I'm with them.

Please tell us more stories -- and especially please continue with the adventures of Sara and how she "makes love" to men she meets. I can't wait to read more stories from you.

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