First time

Now that i had learnt how to please a man it was about time i put it in to practise on a real man.

Unfortunately at the time i was still rather shy ( i always have been probably always will ) and dint quite know how to go about finding me a man who could take care of me, luckily i had a friend who just happened to know a gentleman who would be willing to (as she put it) break me in, out of my shyness i allowed her to set up all the details of where and when with only one request from me being that i dint care where she was as long as she was in the same building as me just in case i needed to escape.

With time and date and location sorted now it was time to decide on my look and outfit (it wasn't going to stay on forever but i wasn't going to go in just my lingerie) both me and Kelly agreed that seeing as it was my first time that i should go for a virgin white colour so that gave an excuse for a shopping trip as i needed to get a complete outfit so i started with shoes thankfully i have small feet so i was able to find some nice white slightly slutty heels after my foot wear i purchased some new white lingerie from a bridal store and finally finished the outfit with a nearly see thru white knee length dress.

2 days after my shopping trip i went to Kelly's house as that's where it was all going to happen i got there 2 hours before my mystery fella was due to show up so as to get ready and get any last minute worries out of my head before he arrived.

After saying hello to Kel and thanking her for letting me use her house for the activities i went to her bathroom and showered and got my self completely clean inside and out next i proceeded to put on my clothes once i was dressed i called Kelly as she had wanted to apply my make-up and sort my hair that brought the time up to where he would be arriving in five minutes Keely went back down stairs to be ready to greet him and give me time to prepare myself.

Shortly after what seemed like forever i heard the doorbell and then heard the exchange of voices as she welcomed him in and informed him that i was just finishing my make-up and escorted him into the room and offered him a beer she then came up to me to make sure i was okay with doing this and go over what i would say if i wanted to abort halfway through.

A couple of minutes later i walked into the room he was sat in i looked him up and down then walked across to where he was sat and sat next to him.

We sat and chatted for a while and i found out that his name was Tom after a while i noticed my self staring at his crotch apparently he had noticed me dong so but hadn't said anything i apologised and he told me not to and we started to kiss this being the first time i had kissed a man i felt a little bit nervous but at some point they seemed to disappear and were replaced by a sense of want and pleasure i slowly moved my hand down his body till i cam across his crotch which i found was already semi erect i let my hand linger there for a while feeling it grow through the material of his jeans.

By this point i had forgot that Kelly had been in the room as well watching all of this so it came as a surprise when she asked me if i wanted to suck his cock after a momentary lapse of concentration i agreed that i would like to and i lowered myself down to the floor and in between his legs whilst i was getting into a comfortable kneeling position tom had freed himself from his trousers and his boxers and i finally got a view of his wondrous weapon and i knew i had to get a taste of it i dint even give him chance to put on a condom i just started sucking for all i was worth using every trick i had been taught whilst practising on dildo's tom just sat back and enjoyed it whilst from behind i felt my dress being removed from me I'm guessing Tom liked my lingerie as he seemed to get bigger whilst looking at me at this point tom told me to slow down as he dint want to cum just then.

I stopped and suggested that maybe we should go upstairs so that he could make me feel like the girl i wanted to be so i lead him up the stairs and to the guest room and onto the bed here Tom laid me down and started to remove my lingerie until i was on the bed in only my bra and my heels by this point i was nearly begging him to slide his nice juicy cock in my tight virgin pussyass Tom ordered me to suck him hard so that he could fuck me.

After a couple of minutes of sucking on his rod he pulled out of my mouth and told me to get on all fours he then got some lubricant and buttered my up so that he could slide in my easily then i felt it as he slowly fed his cock in me it hurt at first but the pain slowly subsided and i began to enjoy his cock in me just as he was pulling out for the first time i told him to leave it in my for a minute so i could get used to the feeling of having him there.

Slowly he began withdrawing and did pull himself completely out then thrust all of himself in in one go causing me to yelp then me slowly at first started to fuck me gradually building up till he was going at it like there was no tomorrow then he slowed down to a softer slower pace as he said he wanted me to feel various styles of fucking after 45 minutes of him fucking me hard and slow i had changed from a shy little sissy to a cock addicted slut and i felt comfortable in asking him how i felt i needed it and i started begging him to " fuck me harder, come on faster, harder, there you go ,come on fuck the living shit out of me, make me a true sissy slut" a few minutes more Tom informed me that he was going to cum and asked me where i wanted it once again Kelly who had heard me and had come upstairs just in time to hear him ask that answered for me with "cum in her ass make him feel what its like when a guy cums in her pussy" and so i got my ass filled with his seed followed by him shoving a tampon in to stop it from leaking out of me after a couple of minutes i offered to suck him clean before he left he accepted so once again i found myself kneeling between his legs sucking on his cock taking him in as deep as i could and going to my gagging reflex but i din't care that it was making my eyes water and ruining my make-up as all i cared about was sucking him till he erupted in my mouth once again tom informed me of him about to cum so i stopped sucking him and just knelt there with my mouth open and him jacking onto my face after that he said his good byes collected his clothes and left.

A few minutes later after getting redressed i joined Kel in her kitchen and chatted about how i had felt and how she had heard everything downstairs and had played with herself listening to it all we finished the bottle of wine i woke the next morning in her guest room having fallen asleep with cum in my ass and it on my face with ruined make-up