A College Surprise

I was in my 2nd year at college and was sharing a house with 4 other students.It was summer and for 8 weeks I was getting the house to myself. My parents had gone away for summer and I had decided to stay. I had been a cross dresser and panty sniffer for some time. The house had one girl called Ruth and I had sniffed and jerked off with her panties but hadn’t dressed in over a year. Ruth had left a lot of clothes and after a couple if days the urge to try some on was too much.

As I went through her room I found a black basque, black lace thong and black silk fully-fashioned stockings. Her boyfriend, Rich was a lucky guy. Ruth was my height and we had similar builds and I was able to slip into the lingerie. Even better was the pair of red stiletto shoes. For once I was glad that I had small feet for a guy and slipped them on. My cock was rock hard (at 7.5 inches it gave a lie to the line about men with small feet)

I was now lost wanking playing and myself with my ass. Like most cross dressers I was straight but when in femme I always felt a little like a cock slut. I had been enjoying the feeling for about 10 minutes when I heard a cough. Panic stricken I opened my eyes to see James one of my housemates looking at me with an expression of surprise and humour in his eyes.

“Well...ell Dave’s a girly sissy.. I never knew” he said smiling.

“Look “ I stammered, “This is not what it looks like. I’m not gay”

“Yeah” he said, “Dressed like that you’ve never looked straighter. I must say you look good.” Despite myself I was flattered by that comment. I quickly tried to explain although I cross-dressed I was straight and had never been with a guy. James knew my girlfriend Claire and had heard us fucking often enough. (The walls were thin and we all knew when were getting laid)

“ I hear you and I can see why Claire smiles so much.” He nodded at my cock now rapidly shrinking.

“But you have to admit you look pretty girly at the moment. Now I’m sure you don’t want Ruth to know about this and the whole Uni. Now my plans have changed and I’m staying here for the summer. If you want to keep this quiet you need to make it worth my while” he said. I couldn’t believe James wanted money off me. I pointed out I was a student and had very little money.

“Not cash Dave, I think you can help me in a whole other way.” To my horror he was unzipping his jeans and a hard cock was being pulled out.

“No way!” I cried, “ I’m not gay.”

“Well Dave looks like Ruth finds out. Rich beats the shit out of you and some people will believe the rumours and even if not you’ll be a laughing stock. Claire may dump you. I’m not gay either but I’m horny and Jane is away all summer. Shame to waste my cum wanking.”

I knew I was in a bind and I had to admit I had fantasised about a moment like this and had always admired James body. I was looking at his 6 inch long and thick cock with fascination. James walked over to me and told me to get on my knees. I slowly dropped and stared at the engorged purple end of his cock. His male muskiness enveloped my nostrils. He stroked my hair and slowly pulled me towards him. I put my tongue out and licked his cock. I was surprised that the initial taste was not too bad. I began to take James in my mouth. I felt filled and heard James moan. Remembering how Claire pleasured me I began to suck and wank James. His moans grew louder and to my surprise my cock got harder. After a few minutes I felt his buttocks tense and then hot salty cum flooded my mouth. I wanted to gag but James held my head in place and I had to swallow. James pulled his cock out and jerked the last few drops of cum onto my face. James picked me up and shockingly kissed me his tongue probing my mouth his hand caressing my arse and legs. I felt myself respond caressing his firm arse and feeling his muscular chest wanting him. He pulled apart from me and took off his clothes. I wanted this masculine young man to be mine. He took me to the bed and lay me down. He looked at my hard cock.

“One good turn deserves another” he smiled. “ Grabbing my cock he wanked me off. It wasn’t long before my cum was shooting over his hand. He proffered it to me and I licked my own cum off. He put my hand on his once more hard cock and looked at me.

“Looks like a fun summer.” Despite myself I couldn’t help but agree.That evening concluded with another wank each and me eating James’s cum again.We went to our respective rooms and I lay awake confused. At turns repulsed by what happened and turned on by thoughts of James’s body and cock. I slept fitfully and woke up to an empty house.I dressed and started work on the proof reading I was doing to earn money over the summer.

In the early evening I heard James’s car pull up and he walked into the house. He smiled and greeted me. He handed me a holdall and said, “ I’ve got you a present” I looked in the bag and saw an array of female clothes, lingerie and a wig. I knew James must have been to the college theatre. He was a leading light in drama society.

“You can’t wear Ruth’s clothes all summer. We’ll get them messy” he grinned. “ These should fit you. I’ll even do your make up.”I must have looked surprised.

“Well if you’re going to dress up best go the whole hog.” He took my hand and led me to his room. He took make up out of the bag and began work. He had learned all the jobs in the drama soc and had told me he sometimes did Jane’s for her. A blonde bob was slipped on and adjusted. He then told me to select an outfit. He went out and I looked through the bag. I slipped on some black lace hold ups white lace boy shorts, a white bra and filled it with the stage bra fillers and then put on a red jersey mini dress and black high heels. I teetered down stairs knowing I looked hot. James let a low growl and motioned me over. He pulled me on to hid knee and kissed me deeply. I felt my cock stir. We kissed for a few minutes when there was a knock at the door. I went to get upstairs when James grabbed me.

“I ordered pizza and you are going to answer the door and pay.” I nervously opened the door and saw a middle aged man. He looked up and smiled. I saw his eyes crawl all over me. He asked if he had the right address and in the most feminine voice that I could muster I answered that it was. He handed over the pizza and I paid. His hand lingered longer than necessary in my hand. He leered at me and said he was happy to deliver any time day or night. I thanked him and said good night. Shakily I walked back to James with the pizza. He was smiling and I could see his jeans had a tent in them.

“You look like a hot slut. That guy is going back to his car and will wank off thinking of your body under his and his cum filling your cunt. If only he knew you only had an ass to fuck.” I couldn’t help but feel excited. We ate and then James once again took my hand and led me to his room. He sat me on the bed and whispered in my ear.

“For the rest of the summer when I’m here you will dress and I’ll call you Kristina.” I nodded. James stood and undressed his hard body turned me on and I yearned for him to make love to me. He told me to take off my dress. He looked on appreciatively his cock standing proud. He walked over to his bedside table and picked up some KY jelly. I knew this time it was no blowjob and I was going to be fucked. He told me to lie on the bed and slowly began to lube my hole putting first one then two fingers up me. Claire had fingered me and put her dildo up me a few times. (She was hot and dirty). So I was not new to the experience.

I writhed in both shame and desire. James slowly started to slide his cock in me. He wasn’t as big as Claire’s dildo but it felt much better. Eventually he was fully in and fucking me. He looked in my eyes and then kissed me. My legs wrapped around him and I thrust towards him feeling my hard cock on his stomach. After about 20 mins I could feel James begin to tense and the he cried out as he cum began to shoot in my arse. He collapsed on me and kissed me deeply.

“Kristina you are one hot fuck” he panted. I noticed my cum on his stomach and realised the fucking had made me cum too. The rest of the night was spent in fucking, sucking and me rimming James.

I was now his plaything.
100% (31/0)
 
Posted by webbyhose
1 year ago    Views: 5,388
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1 year ago
my god! u have to continue this!
1 year ago
that was sweet..Better to be the girl.
1 year ago
Great story! Makes me want to get ahold of an old friend from high school!
1 year ago
This is sooooo fucking hot! Thx
1 year ago
loved this story
1 year ago
fantastic story thanks
Jay
1 year ago
more please!!!!!
1 year ago
Fucking great! I hope u write more ;)