The Office Sissy XX Ch. 02



The smell of Dannie’s pheromones was making me giddy. It had been so long since I had last tastes sissy clitty; too long. My mind flashes back to boarding school, Gloucestershire. I was young, under age by English law. It was just after the summer play, and James had decided we should change costumes; boys wear the Shakespearean dresses of the girls and vice-versa. We were drunk from cheap cider, so prevalent in the boarders, and would have agreed to anything the leading man had said.

Without a care we all stripped to our undies. But James insisted it was all or nothing and dared us to swap undies as well. I was young, naive, but to be honest I was also too slim and yet not as self conscious as I am now. Dresses and doublets were exchanged. Buttons, no zips, half of us struggling with tights, others trying to hide budding breasts. The girls of course had to help the boys with wigs and make-up, we looked a sight. I felt strange but aroused, the clothes were alien and seeing my school friends crossdressing seemed to be so erotic.

Jamie came over and commented on how he loved the theatre and all this ‘role playing’. He explained he was a method actor and had to get into character; immerse himself in a role as it were. “Call me Mistress Jamie” he said as he curtsied. Leaned forward and kissed me, as soft as any girl would.

She, one could only call Jamie “she”, looked as sexy as any girl I had ever met. Jean had done an excellent job on ‘Mistress Jamie’, but what she couldn’t hide was an erection in her dress. “This will never do” she giggled, and lifted her dress. Jean has always worn sexy thongs, so daring, and they looked fantastic on Jamie. It was the first time I had seen a sissy boy, shaved clitty and pink erection. Jamie licked her lips and winked. I could feel the warmth of arousal fill my genetalia, and at that very moment, I knew that sissy clitty was for me.

I knelt before Jamie’s hard clitty and kissed it. I opened my mouth, and in an instant I am back in front of Dannie once more. She is stunning in my dress and heels, her clitty at my red lips. I take her into my practiced mouth, my tongue flicks under the shaft and she moans. My hands rest on her thighs, feeling her nylons; stroking her.

I take my left hand and cup her sack. She slides forward giving me access to her dildo. I take the hint and slipped my right hand below the other. She was pushing the dildo out, with significant force. She was obviously used to xslot penetration and needed it for fulfilment. I reach for the end of the dildo. It is so warm, not the cool rubber phallus I had placed in her only minutes earlier. In and out, in and out. It is smooth and offers little resistance as I played with her pussy. My sucking mimics the stroke at her pussy hole as I climaxed her, and then cruelly, slow and let her relax; then only to start again. I am well practiced at giving head to sissy girls, but Dannie is different. She loves the attention, a virgin perhaps, but there is no doubt that masturbation and dildos are not new to poor little Dannie.

I start to feel sorry for the poor little sissy, and as she climaxed for the fourth time, I push on to orgasm. She explodes, emotionally and physically. Pure cream fills my mouth, the dildo descended one last time and she screams in a true female voice. Starting as an alto and ending in a shrill soprano.

I straighten up and lean forward, my mouth full of cream. I make to offer it to her, but she turns away, tears rolling down her feminine face. She pulls her legs up to her flat chest and assumes the foetal position. She is crying, not like a girl, but as a baby. I cover her with a throw and pick up the dildo. I quickly tidied up and wash the dildo thoroughly, licking it first, sucking it, then soap and water. Heaven knows I love to suck. When I return Dannie is sound asleep. I look at my watch, 8:05. Plenty of time.

Chapter 4

I go back to the bathroom and fix my make-up. A little powder and lipstick and I am the beautiful Penny again, sex goddess of the seventh floor. Now for shopping, me thinks.

I pick up my tan gabardine trench coat and wrap it around my hour-glass figure. It’s retro, and cost me more than I care to remember, but it’s comfortable, and makes my ass and legs look great. Handbag and away we go.

Three years ago, mum had been diagnosed with breast cancer. She is in remission thank heavens, but it did mean I know where to get fantastic prosthetic boobs, and real close. I hail a black cab, its amazing how London cabs have migrated like cockroaches out of the metropolis down the M4. If it wasn’t for the Severn Bridge, I’m sure Wales would be over-run.

A quick ride and I am outside the small industrial unit in west Swindon. I step over the threshold and into a pleasant but functional reception. “Still open I see”, I smile at the receptionist. “Ms. Jones isn’t it”, her face xslot Giriş lit up, “Long time no-see”.

I remember Rachel very well. We had been out a couple of times for a drink, which ended in bed. But that was, must have been, yes, two years ago. “Rach, darling, why so formal”. I make to air-kiss, but am greeted by one on the lips, with a slight taste on tongue.

“Sorry Pen, it’s been so long, too long.” We hug for slightly longer than is polite, but not long enough for, ‘shag me senseless you sexy bitch’. I have swung both ways since an early age, and be it men, sissy boys or genetic girls, so long as we have fun and no-one gets hurt, what the heck. I am happy with whom I am, and those I choose to bed, appear to be happy with my somewhat unique variety of abilities.

“Whilst I wish you were here to invite me out, I suspect either your mother has misplaced one of her false boobs again, or, more likely it’s some thing more personal.” Rach new my secrets, hard not to when you get intimate with any lover.

“Personal today Rachel. I have found another plaything, let’s call her Dannie for the sake of arguement. I need a pair of mid-range c cup with hard nipples, rock hard. I know you stock them, I’ve had them before. Skin tone and I need surgical glue, the best you have.”

“He is a lucky boy, or should I say sissy boy?” Rachel l laughs so beautifully I want to kiss her here and now.

“Tell you what; if you can give me staff discount, I’ll let you fit them to her.”

“You’re on Penny, be worth it just to see you in action one more time. Do you want them gift wrapped.” Again she laughs that silly little giggle that used to make me hot.

“I’m off to the outlet centre, I’ll pick you up in 45 minutes; I have a few more essentials to get.”

Chapter 5

It’s not hard to pick up a taxi when you have legs and hips like mine. To be honest the legs are mine, but the hips and ass needed work. Let’s not get into that now, needless to say, when you fork out several thousand pounds on your ass, it ought to stop the traffic.

The outlet centre next to the railway museum stays open late. Plenty of time to pick up a few essentials. Anne Summers, Next, Triumph, plenty of choice but only half an hour. There will be loads of other occasions, and they will be with Dannie, enfemme, poor little sissy boy.

Essentials first. Two bras, four panties, four thongs, five pairs of stockings, mix of holdups and conventional, a short xslot Güncel Giriş corset with suspenders, and last of all, a red silk night dress. It is full length, but a waist high split on the left side.

Dresses, three, red, black and electric blue. Plunging necklines and a little too short for modest, a little too long for slut. My favourite length. Heels to match, none shorter than 3 inch, and why not, a couple of clutch bags one black and one to match the electric blue dress.

Accessories, necklaces, bangles and earrings. Shit I forgot, are her ears pierced? Who cares, they will be soon. I wish I had time to try these on, the undies, dresses and bangles, but then they wouldn’t be Dannie’s would they.

Now for some fun. I just love sex shops, even high street ones. First a real dildo, shaped like a real cock, bell end, ridges and balls. 12 inch and medium girth. It smelt divine, and I even gave it a sly lick. A chastity belt, no good getting second best, and metal is always best I find. I prefer separate dildos, but a good shield for the genitalia is a must. The one I choose is stainless steel with a large flat face plate for the clitty, a thin but substantial chain that acts as a thong, but with two pincers like semi circular waist bands which pivoted at the face plate and meet behind ones back. The chain provided the adjustment and a delicate combination padlock provided the necessary control.

A double ended cock gag in black and a leather gimp mask rounded off my purchases. I am the last customer that day, and most likely their most profitable. As I walk towards the taxi rank, purchases in several bags, my phone rings.

“Hi Rach darling, are you chickening out?”

“No Pen, rather the opposite, I closed early and thought you might need a lift.” I glanced around and immediately see Rachel flashing the lights of her Mini Clubman. I turn and with an exaggerated swing of my hips and boobs, stride over to her car. I love to see men ogle me as I walk. It makes me realise that all the hard work of becoming the woman I am is all worth while. It also doesn’t harm to make Rachel a little moist in the neither regions.

I open the front passenger door of the Mini and release the rear ‘suicide’ door to the rear seats, placing Dannie’s treats on the back seat. I closed the rear door and reverse into the front seat, bringing my legs in last. In a flight of fancy, at the last second I part my knees slightly and swing my hips over slightly to show a silly teenage boy at the bus stop the top of my stockings and perhaps the hint of my panties. Such a prick tease even now. He visibly blushed, and to make up for it, I pouted a kiss as we drove off.

To be continued…

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