Sissys First Anal

Having come to terms with the fact I was a sissy gurl, life was about to get a little more interesting. Peter; the boy who lived in the house across the way had given me my first taste of cock and I was already addicted. Things were a bit awkward between us at first seeing as how he didn’t consider himself gay but he started to warm up to what had happened. Another weekend arrived and my parents were away and Peter suggested coming over for a sl**pover. I was ecstatic. I nearly creamed my panties at the thought of it.

After seeing my parents off I decided to have a shower to clean myself up in praparation for his arrival. The knock came on the door as I was exiting the shower. I wrapped a towel around me just under my arms as a girl would do and ran to the door to see my man. He entered carrying a duffell bag with him. I sat him down and offered him a drink. The liquer cabinet was left unlocked and I thought it would be good to loosen us up a little. I poured two glasses of whiskey and sat across from him. We both took a swig, he swallowed his with ease, I had a bit more trouble burning my throat off, I would never take to drink. He laughed at my expression as my eyes started to water from the stinging.
“You really are a sissy”, he said with a smile.
“I think so”, I said through a shy laugh.
We then discussed what had happened between us the last time he was over; how I revealed my love for ladies underwear and how I ended up sucking his cock.
“I ran out on you after that”, he said.
“It was because i was confused. I liked it and didn’t know what to make of it”
“I understand”, was my attempt at a response. He went on
“The thing is, I’ve been thinking about it ever since, how good it felt, how good you looked sucking my dick and I know I want to do it again”

I almost fainted. I hadn’t stopped thinking of that afternoon, how big he was. How it felt to make someone moan with a little flick of my tongue. How right I felt submitting to him and now I knew he felt it too. I had to ask to be sure.
“So you would like to do it again?”
“Yes, would you?”
Oh God Yes!
He had a condition.
“the thing is, I’m not gay. A girl sucked my dick the last time I was in this room and that girl is who I want. Clear?”
“Crystal”, I responded.
“Thats why i brought the bag. Open it”

I had forgotten about the bag, I unzipped and discovered a treasure throve of ladies clothes.
“They were my s****rs”, he explained.
“She moved out to college last year and left two wardrobes of the stuff behind, I was thinking you could wear them for me.”
I felt like I’d died and gone to heaven. He could tell I was pleased.
“I figue I might go and take a shower while you put something on, maybe then we can have some fun.”
I was immediately up the stairs to my room, bag in tow. As he showered I tried to put an outfit together.

There were various skirts and tops to choose from. Was trying to find something to really get the bl**d pumping. I found a lace negligee to wear as underwear, my favourite holdup stockings, and when I saw her school uniform there I knew what I had to do. I had long been jealous of the girls school uniform with the platted skirt and white sheen blouse with the cute bow tie. I knew I would look quite the slut in it with stockings showing under the skirt so the decision was made. I raided my mother’s make up for a dollap of lipstick and eye liner. I was a long way from the finer points of make up but at that point in time it more than did the trick. Checking myself out in the mirror I looked quite the girl, my hard cock poking through the skirt not withstanding.

I made my way downnstairs to find Peter already waiting for me. Having seen where the household porn was hidden he had already tracked it down and had some hot action playing on the television.
“You look so good”, he told me.
I blushed my first compliment as a girl. This was turning into a greater day than even I could have dreamed.
I thanked him and asked him what I could do to repay him. He smiled, grabbed me by the waist and said,
“Its time you went back upstairs.” With that no more words were spoken. I ran up the stairs and he persued. Into my bedroom and he grabbed me. An embrace at first and then a kiss straight on my painted lips. I shivered with excitement. I felt his tongue press against my lips and I opened up and let him inside my more than willing mouth. We stayed on our feet tongues locked for a minute straight breathing in each other. When he released I gasped. He took a step back from and started to undo his belt. I immediately dropped to my knees and took over for him. I had been having sl**pless nights dreaming of seeing his cock again. As I undid his fly and pulled his boxers down it sprung out at me bigger and more beatiful than I remembered. I didn’t even have the sense to tease it this time I just opened up and took the whole thing in my mouth. He’s gorgeous cock was hot and ready and the taste of his pre cum was already enveloping my senses. He moaned as I slid my mouth up and down his impressive member. As I paused for air I would work his dick with my hand pulling down his foreskin to reveal his full helmut. His cock was glistening with my spit and precum and I was drooling from all my eagerness. He grabbed my hair and kissed me licking up both our juices on his tongue, he then declared he wanted to fuck me.

I was prepared for this scenario. Having done some research into this business I knew some of the requiremnets and had stored some vaseline under my bed. I reached under and pulled out the tub. Peter knew what to do from here. He placed me on the bed face down with my virgin ass facing the ceiling. He hiked up my skirt and opened the jar. He gently started to massage my hole. All this time my own cock had been hard as a rock as I felt his breath at the back of business I started to drool pre cum. He then placed his fingers in my ass for the first time. It was a strange sensation as he opened me up but after a minute or so I was ready. He fed his cock into my mouth on last time then took his place behind me. He placed his cock at my fuck hole and worked his way in. The sensation as his cock opened me up is hard to describe but it is somewhere pain and pleasure meet. He went gentle at first but as soon as we were both ready he started to thrust himself in my virgin pussy. I moan with pleasure as he fucked me, I was more than ready to give myself to him. I had noticed my own cock had started to shrink but that made no difference to the pleasure as I started to squeal. He groaned deeply as he started to find his groove and then I felt it. Shoots of hot sperm filling my used hole. I started to cum myself from the sheer excitement of it all. We then collapsed on the bed, me into a pool of my own spunk as his hot creamy cum started to ease its way out of me. We were spent. I was a little concerned about Pete’s reaction now he had cum but he wrapped his arms around me and we spooned on the bed as we both recovered from our morning’s fuck.

We would continue to have fun on our sl**p over. He told me that from now on when weekends came I would be his girl and as you might assume, I was more than happy to agree.

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