Let me first start by saying I’m a straight guy never in my life would I have thought I’d ever do this. (ok some of that could be a lie)
The office has always wondered about Simons sexual preferences very camp talking, not bad on the eye and good skin, dyed hair seems to always be a hit with the ladies he was always coming in each weekend telling everyone about his conquests. He ended up having his heart broken by his previous fiancée making him becomes bit of a player.
Shortly after his breakup he met a girl and decided to take him up on is offer replacing the ex on holiday.
Whilst on holiday he once again became the talk of the office by dressing up in a blonde wig and red dress clearly a drunken night the new girlfriend present in a few photos.
When he came back to work, we jokingly brought the pictures up to him where we were all surprised when he said, "oh yeah that’s my stuff I took for holiday! nothing by it the new girlfriend is bi! so just thought it would be good foreplay!"
Unfortunately, after this - this girlfriend did not last too long!
Weeks go by I all kept thinking about is Simon dressed in the blonde wig and what lengths he would go thru for the results in the bedroom.
At this point I decided to make a fake snapchat account jotting down his username from my main account, knowing full well the acceptance of this account would come pretty swiftly, I panicked when he added me thinking what should I say or do? He quickly he sent 3 or 4 messages "hi" "do I know you" "how are you doing". I logged out and thought this too far!
It comes to Friday Lunch at work he bumps into me the kitchen whilst making tea. "Any plans this weekend Simon”, “no he replied I was due to go out on a date but that just been postponed" - I laugh this off "oh well i guess there will be another!"

I knew this would be my time to strike so I quickly ran to the side room and loaded up SC and replied to yet another message he had sent to my fake account whilst I was logged out.
After a few messages and some flirty ones, I came clean "I’m going to be honest with you here and I understand if you block me, I’m a guy and we do know each other. I know you like the play dress up I know what house you live at would you mind if I come and fuck you anonymously IF this is something you’re into… I’m sorry if I have mistaken what I know about you. All I ask is that you where a blindfold".
As I headed back to my office, he shouted down the hallway "you were right there may well be another" I just laughed and turned away.
After this comment I was sure I was in then nothing - oh well it was fun whilst, it lasted... until that evening.

Simons typing..."22:00pm if you "know" where I live the door will be unlocked 22:15 its locked, I’ll be upstairs on the bed”.
Wow am I really going to do this? In I go!
I knocked the door as I walked in the house giving him notice that I was there, locking the door behind me.
As I walked into the bedroom, he was sat on the of the end of bed. The bed was huge looked pretty snug in the tight box room with two draws either side of it.
She looked stunning I could not work out if it was the same blonde wig I had seen in images before up in a bun like a teacher with a pen in the hair black lacey bra and matching underwear finished by some shin high boots. my jaw was wide open even more when I see his semi poking through the top of the thong.
I choose to talk in a deep voice "what’s your name" Shannon he replied in a near prefect impersonation of a woman.
"Now Shannon you’re not going to remove that blindfold until I leave is it that right" she nodded "Good, now get on all fours with your head towards your pillows”.
as Shannon moved into position I stripped down and gave my cock a couple of tugs laid on my back and shuffled up in between her legs placing both my hands on her panties pulling them down until her penis was fully hanging down oddly still semi and limp and this point I froze waiting for it to spark into life Shannon was roughly 4inchs uncut different to my cock. I slowly watched the cock grow bang there it was fully erect standing to attention, I grab hold of her cock and put her balls in my mouth- a couple of slight moans came from above me. After sucking Shannon’s balls, I put out an assurance that I’ve never done this before she giggled, you’re doing fine! I move rearranged myself slightly and plucked up the courage to suck her cock running my tongue in between the head of the cock and foreskin stopping and wanking her off before going to town on his shaft with each blow feeling a throb from her dick. I pull myself out from underneath her crotch and demanded she opened her mouth - wow she knew what she was doing she knew what to do from blowing it, deep throating it fast, slow and long wank strokes and shoving a pre lubed finger up my arse I was surprised I didn’t finish in her mouth right there and then.
"Do you mind if I fuck you now with a nervous voice break in between" "I’m surprised its taken you this long I only wanted fucking she joking said".
Wanking at home my attention had turned to gay porn and watching types of positions I would like. I kneeled down behind and she sort of sat on my knee handing me the lube I slowly entered my cock in to her arse giving her several awkward thrusts before mid-thrust I reached around and grabbing her cock wanking it like my own! With each tug a man’s moan and groans creep out in between the girly one before one big one! I never felt so much cum on my hand it was amazing I made her cum first! I think Shannon was quiet surprised this which only encouraged me more I got confident and forced her forward into a doggy position I’ve never pounded pussy as hard as I was fucking that ass "cream me Shannon pleaded" faster and faster I went until I cried out from the force of my cum!

Wow I was again in shock of the quick 25-minute fuck had gone, I watched as the cum dripped out of her gaping hole. I grabbed my clothes and left wishing I had stayed.
Add me on SC-julianedwards92