Sissy Dress Fun – A Night Out With Mistress.
I have been seeing a Sissy Cross Dresser – a proper Nancy Boy, and Nancy is his chosen name.
Nancy has been a regular of mine getting on for a year now – at my Huddersfield chambers.
The scenario is very much the same each time – full dressed in sissy frilly items. Thoroughly sissy dress – from the frillies on the outside – to the matching frillies as the underwear.
From there, the sessions progress to stocking worship, and strap-on play, for the climax! He likes to me give his back pussy a good, energetic fucking!
During his sessions, Nancy keeps going on about wanting a man – a dominant man – so the last time he got nattering on this subject, I cut him short to ask him all the sordid, dirty details of just what he would want should he be picked up by a dominant man!
“What I want most, said Nancy, is to go cruising for males in the gay village, over the M62, at Manchester. And then when I get lucky and some great muscular, well hung guy tells me I’m a pretty slip of a thing, and do I fancy being bent over and shagged down a dark back yard in the village, I get damp with excitement!”
So we set the arrangements for this trans-pennine rendezvous.
To set the right impression, I took Nancy on a shopping trip to Primark.
To get the basics right, from the inside to the out, we first went to the secret desire section – some elegant lingerie and panties to give the dominant boyfriend something to grope over, and pull at, to get up inside Nancy’s back passage!
For some modesty, Nancy wore a knee length rain mac. Arriving back at the Chamber, I got to work on his transformation – to make him a dainty dish for the gay village!
The time flies when busy with a cross dresser, already getting on to early evening, and we had a train to meet!
During the journey to Manchester, I noticed Nancy getting increasingly on heat! I knew the thoughts he was thinking – thoughts of cruising about the village for a bit of rough – we happened to be on a train with gangs of men comimg home on leave from barracks down from York – with Nancy already on the look out for any good prospects in the train toliet with some army guy!
“Fucking control yourself” I whispered in his ear, “wait until we reach the village, you slut! In any case, the guys are friendlier in Manchester!”
After a few delays on the train journey, we finally reached Piccadilly, and Nancy was so much on heat, he was on fire!
As we got further away from the glare of train station, and nearer the gay village, Nancy stripped off his mac – and all heads turned. Wolf whistles and shouts of appreciation at Nancy’s fresh meat!
We went into one of the bars in the village – a good stiff drink – the alcohol did its work on Nancy – raised his confidence, lowered his inhibitions, and raised his heat! We spotted a good looking, tanned guy with moustache, and rippling muscles! He and Nancy made immediate eye contact – whenever Nancy caught the guy looking at him, the good looking muscle man winked and pouted his lips at Nancy!
I shoved Nancy forwards whispering “get on with the business, that’s what you’re here for!”, Huddersfield Mistress.
I backed away to a discreet distance, ordered myself another drink at the bar, and watched the sport between them! I could see the guy holding Nancy close tight to him, smooching, whispering into Nancy’s ear – whispering God only know’s what!
After a few minutes I saw the muscle guy leading Nancy in the direction of the toilets, and I followed them, but still kept a reasonable distance away! I was eager to see Nancy wanting to please his Huddersfield Mistress.
15 minutes passed, but it seemed a good deal longer. First the muscle guy left the toilet, then another five minutes or so later Nancy stepped out!
I pulled Nancy to one side and whispered “so, what happened then, get on with it! tell me what happened!!”
Nancy told the tale “We went into a cubicle, he unzipped his trousers, I could see his cock throbbing hard through his y-fronts” He teased me with this for a while and asked me if I wanted to unwrap it and give it a blow job. I reached for his y-fronts eagerly – but he stopped to tease me saying “unwrap it slowly and steady”, He made me rub my hand over his y-fronted cock!”
Nancy couldn’t hold back anymore, and got the condom on the muscle guys cock like lightening, and started deep throat – almost like second nature! The muscle guy was hard now, and turned Nancy face against the toilet wall, whispering to Nancy “I want to give you a good fucking with my hard cock!” “Please give me a firm fuck, Muscle man, begged Nancy”
“I expect you’d like another drink after that, I offered Nancy. It must have been thirsty work!” “I expect sometime you might fancy a trip to Portsmouth – to pick up a sailor or two!!”