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The Sissy Estate Agent

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By *tephTV67 OP   TV/TS 42 weeks ago

Cheshire

The Sissified Estate Agent.

I took over the family business straight after my Fathers death and my Mother’s illness meant she could no longer go to the office or to viewings. Ours was a small shop and as we were based in Brighton I decided to focus on the LGBTQI community. Due to being a bi Crossdresser. They say in business try to stick to what you know, so as a guy who went to the Gay pubs and clubs it was at those venues I advertised heavily for new clients, people I’d spent plenty of time socialising with.

It wasn’t long before I was getting plenty of new business in, the pink pound was filling up my Bank balance nicely. However I kept my crossdressing out of the office not all of my gay clients would approve and some would avoid doing business with me. However on occasion if it was for a fellow TV/CD or admirer I would don a skirt and blouse to encourage them to choose myself over rival agents. I maintained a professional relationship with anyone I met and rebuffed gently any seduction or request for a more intimate relationship.

However one day this professionalism changed for a particular client who came into my shop one Monday afternoon. I had been busy in the morning and at first didn’t see him come through the door, I turned around and suddenly seeing a big guy in front of me I gave out a very girly shriek.

‘Sorry, didn’t mean to scare you’ he said with a slight amusing tone.

At 5’7 I was average height but this very handsome black man must’ve been over 6’2.

‘That’s Ok’ I said knowing my face would be red with embarrassment.

Once initial greetings had taken place we sat down to talk business. He had 10 apartments that he wanted to rent out, predominately to the gay community or young professional workers. I had been recommended by a gay club owner who’d given out my card and address. It’s then when he asked a question that I wasn’t expecting.

‘Do you crossdress ?’

I was a bit taken aback but some of my clients knew and I wasn’t ashamed of it.

‘Yes, I do but only at night or special occasions’ I answered.

‘Special occasions ?’

‘Yes, some clients know of my alter ego, so I do dress at times’

‘What does a client have to do to get this special service ?’ He smiled as he asked.

I went even more red as I answered.

‘Well if he gives me his business I will happily view an apartment dressed as Samantha’

‘I will happily sign a contract with Samantha’ he said and we agreed to meet at one of the apartments the next day, to take photos and measurements.

Part 2 when things get steamy very soon.

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By *essiewhoreTV/TS 42 weeks ago

Grimsby

Oh go girl go x x

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By *ick manMan 42 weeks ago

longford

Goood start

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By *hil911Man 42 weeks ago

Solihull

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By *ucksguy2000Man 42 weeks ago

aylesbury

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By *tephTV67 OP   TV/TS 42 weeks ago

Cheshire

Part 2

I got up early for the viewing with Simon so I could ensure I had plenty of time to change from boy to girl. I had found him immensely attractive and manly so I wanted to dress to impress.

My makeup was applied carefully to try and match my outfit, pink eyeshadow and blusher, a slightly darker pink lipstick for my lips. My own hair is blond so I styled it more femininely at the front and added hair extensions to the back to make it longer. Now my hair rested softly on my shoulders and would gently brush against my cheek in the wind. Such a feminine feeling when outside or in.

As I needed to go dressed for business I really wanted to express my feminine appearance by wearing something slightly over the top. There in my wardrobe I found the perfect outfit a very dark pink suit, the skirt would come down just above my knees and the jacket loose but fitted at the sides, underneath a pale pink blouse with a very prominent bow that hung over my breast and long flowing sleeves. The lingerie was also pink, silky knickers and bra, obviously just for him a suspender belt and stockings, with some pretty pink shoes to top off this sissy business look. I didn’t know if something was about to happen but I wanted him to be impressed if it did.

Brighton sea front was only a 15 minute drive from my home and I was suitably excited and nervous about meeting my client, had I gone over the top with my outfit ? Talk about the pink pound and this girly guy was dressed comparatively like one.

I must admit the apartments looked great from the outside as I parked my car. But more impressively was Simon who started to walk towards my car as I was reversing. As the Gentleman I suspected he was, my door was opened and his great big hands held mine as he gently helped me out of the car. He then took a step back to look me over, his smile and apparently appreciatively nods made me blush (again).

‘You look fantastic’ he said

My blush was how I responded.

‘Please let’s go in and I’ll give you a guided tour around my show apartment’ he said.

As we walked together into the block towards the lift, occasionally his hand would brush against mine sending shivers up and down my spine. I desired him desperately and I think he knew it. In the lift he just stood opposite looking at me, no words just a smile and a lick of his lips, lips I so desperately wanted to feel against my own.

The apartment was a one bedroom and it wasn’t long before we entered that room. Me first with him behind me a presence I could feel, an electricity between us which was difficult to hide. I turned around and he had closed the door his massive frame impossible to get by, even if I wanted to.

‘Come here’ his hand outstretched

I held his hand as he pulled me towards him.

‘But…’ the sentence wasn’t finished as his lips were pressed against mine. At first a gentle kiss but then I felt his tongue pushing through my pink lipstick painted lips. He had turned me around so my back was against the door pinned to it as his tongue invaded my mouth. Also I felt his hand inside my jacket caressing my breasts through the chiffon blouse.

Throughout this erotic assault he was kissing me hard on the mouth and occasionally letting me breathe as his lips were on my neck, shoulders and straight back up to my mouth. My hands were now on him I wanted to please this Adonis, feel his cock grow in my mouth but he was too busy pulling off my jacket and leading me to the bed.

I had an opportunity to move away slightly as my jacket fell away and immediately fell to my knees, my hands reaching to his belt and the bulge I could see in front of me.

For once his dominance over me relaxed and he allowed me to pull down his trousers, then his Calvin’s underwear to release his very large cock. I grabbed hold of it and started to lick and hold it against my face an old trick is not to put it in your mouth immediately, but caress it, kiss and lick it but wait until you can see and feel that it’s at it’s hardest, then plunge it in deep into your mouth, lick around the head allow it to explore all parts of your mouth and constantly bob up and down using the tongue to find its most sensitive glands.

Precum had already been present and licked away by myself and I hoped a more substantive amount would be forthcoming if I carried on.

He moaned pleasurably and at times trying to get my head up and his cock away from my mouth, but this is where my power comes from, by using his moans to tell me what is working and how to keep this man satisfied.

Eventually I could feel him getting close but he stopped me, pulled me up and yet again his tongue was in my mouth and he’d taken all of my power away as we fell on the bed kissing each other hungrily. His hands now up my skirt as I was pinned to the bed to await whatever he demanded of me.

Part 3 soon…

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By *oth0712Man 42 weeks ago

cambridge

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By *atehantsTV/TS 42 weeks ago

Petersfield

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By *erri AnneTV/TS 42 weeks ago

Shannon and Costa Blanca

Looking forward to three

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By *cott60Man 42 weeks ago

Perth

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By *tephTV67 OP   TV/TS 42 weeks ago

Cheshire

Part 3

As we writhed around on the bed, kissing and groping each other I felt my knickers being forcibly removed. His grip on my erect cock was slightly painful but also enjoyable as he started to wank me off. The last thing I wanted was him to take me into his mouth I needed him to be masterful and demanding. So I slowly but steadily started to move away, taking his hand off my cock I said I needed to prepare myself.

He smiled when I said that as we both knew what should and will happen next. Now just in my lingerie in a disheveled state I got off the bed. I wobbled slightly as I headed to the en-suite bathroom, my erection receding.

‘Go to the wardrobe I have a present for you’ he said.

I opened the wardrobe and on the floor was a neatly wrapped box. I ripped open the wrapping and quickly opened the box to find a light blue silky lacey babydoll nightie with matching thong type knickers. I immediately started to get hard again as I held it up against me to see if it would fit.

‘Go on then sissy boy, get changed and get yourself prepped’ he playfully said.

I practically skipped to be bathroom desperate to put on this beautiful feminine outfit. The excitement to parade in front of him in this beautiful nightie was starting to make me feel so submissive to him and my situation.

I found some cream and applied it to my bottom I wanted him to easily take my manhood away. I desired to be his sissy play thing and to do away with any masculinity I had that afternoon. The nightie slipped over my head and I felt the silky material cascade down my body. The hem just below my bottom and the knickers barely concealed my erect cock. I then did my best to tidy up my hair and makeup and paused before I opened the door to see my lover again.

I walked out of the bathroom to see him on his phone, I coughed slightly and he looked up at me. His phone dropped out of his hand as he looked me over. I started to twirl around for him allowing the material to rise so he could see my bum and then my erection. I paraded up and down just out of reach as I saw his flaccid penis gradually growing the more sissy I acted for him.

It was when I had my back turned and raising the hem of my nightie to show him my pert bottom that I was suddenly pushed up against the wall.

I was slightly surprised but due to him grabbing hold of my thong pulling it to one side and inserting a finger into me I realised what I deeply desired was coming to fruition. One finger soon turned to two then three and I was being fingered hard all the while as I was pushed up against the wall his powerful body not allowing me any escape. However my moans of pleasure meant he knew that was just the beginning and he had full consent from me. When his fingers were removed and I was led over to the bed and bent over I then became his, whatever he demanded I would supply with my body, mouth or now with my arse.

‘Want it Sissy’

‘Yes, please fuck me’ ‘fuck me hard’ then as he entered me ‘yes, oh god yes’ I felt him getting harder and deeper in me ‘please oh please’ I begged, not knowing what I wanted apprehensive but fully in the moment.

I then felt him against me and knew this was the moment I had taken all of him in me and now he’d pound out any masculinity I had left. He was now in full control of me and I desired him to take full advantage. The first thrust hurt but I could feel a tingling down below, and as he thrust more that tingling feeling intensified each thrust brought more and more pain and pleasure. Something broke in my head and I heard myself screaming out his name, demanding to go faster and harder, even though it hurt the pleasure was starting to override any discomfort.

‘You my sissy now ?’ He whispered into my ear as he pounded away at my sissy arse.

‘Yes, oh my god yes’ the pain had now subsided I now had waves of pleasure as he groped my nipples, kissed my neck in between bouts of hard fucking my arse.

‘I’m close’ he said as I felt his manhood really tense up inside me. I also knew I could finish but I wanted so desperately to hold back.

He thrust even harder into me now, his arm on my neck pinning me down face first into the blanket. I had now not only allowed him to use me and fuck me, but I was enjoying the subjugation I felt as he made me into his girl, his feminine fuck femboy, the emasculated sissy he was going to pump his seed into in a few more thrusts. I just moaned in pleasure offering words of encouragement and demeaning myself even more.

He cried out in pleasure as his final very hard thrust’s eventually released all of his sperm into my arse. I could feel him building up towards it, relaxing myself to allow him easier access and ultimately to enjoy his final moments in me.

As he finished and gradually removed his cock from my arse I felt the smack on my arse cheek. I fell to the ground as my legs felt like jelly. I had been throughly fucked and lost all control and I still had more desire and a need to finish myself off, however what he said next, excited me.

‘Ready for round 2 in a bit’ he said

I nodded no longer able to speak much knowing I had more to give and more to give away to my man.

The End or for that guy the beginning.

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By *eeker of pleasureMan 42 weeks ago

manchester

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By (user no longer on site) 42 weeks ago

Great story.

Steph xx

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By (user no longer on site) 42 weeks ago

Fabulous tale xx great reading xx

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By *idlothian manMan 42 weeks ago

midlothian

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By *ignbeardyMan 42 weeks ago

Leeds

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By *inkyfuntimesMan 42 weeks ago

Northampton

What a great story

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By *tephTV67 OP   TV/TS 42 weeks ago

Cheshire

Thanks for everyone’s feedback

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By *ark_sentinelCouple 41 weeks ago

Andover

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By *ini1275Man 41 weeks ago

stoke on trent

Loving it

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By *cott60Man 41 weeks ago

Perth

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