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  • Jemima's Tale Pt. 05

Jemima's Tale Pt. 05

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Part 1 - Jemima Needs a New Man

Oh I really really REALLY missed having a boyfriend!

All you girls out there know what I mean - nothing is ever quite the same once you've experienced what it's like to belong, sexually, to another man. Before Steve accidentally walked into my life, I'd spend endless hours fantasising about having a boyfriend of my very own, someone I could have a proper crush on and who would enjoy giving me full rein to dress up in sensual, erotic, clothes for his delight - and my own pleasure...

Above all, I dreamed of having a man who would let me surrender to my need to play a traditionally feminine role in serving a full-blooded male lover. When at last my dreams turned into incredible reality, and I actually met a man who seemed to want the same things, I seized the opportunity with both hands, using our love-making to explore the boundaries where my fantasies and my sexuality met, and in the process finding myself opening up, revealing aspects of myself that I could have never known existed.

Through my relationship with Steve I found out that, to totally be myself, I really did need to be with a man. Having someone to dress up for - and subsequently undress for - did seem to be necessary to make my life complete. At the age of 29 I was comfortable with the fact that some integral part of me needed to express itself as Jemima, and that part wanted a lover to daydream about, to tease and tantalise, to offer me the demands of their passion in endless, mutually desired, lust-filled sessions of sex... For Jemima there was nothing, absolutely nothing in the world that compared with the reality of lying there, curled up against your satisfied boyfriend, with your bum all sticky and tingling from a bout of his strong, eager, lovemaking. What could ever equal the mind-blowing thrill of lying spread and open beneath the man you love, giving yourself up to him, the urgent stiffness inside you linking your two bodies together even as he takes your head in his hands to kiss you, long and hard, while you feel his climax bursting into you, throbbing and squirting his seed deep into the very core of your being...

Finding myself once again without anyone to let me express these deep, innermost, desires hit me hard. Really hard.

Over the months, I tried to fill the gap in my life by buying more stuff. More lingerie and shoes, more porn and toys, in fact anything to distract me from the faint nagging ache of remembering. I dressed for myself, inventing stories that had me tying myself up, or spanking myself or fucking myself - all of which provided some short-term relief but seemed flat and totally inadequate compared to the illicit, heart-stopping, excitement of being in the arms of another real live human being.

Although I couldn't have known it, through those frustrating, despairing times, there WAS a new relationship waiting in the wings. In a way I could never have predicted, it would take a leap in the dark, letting the aspect of me that was Jemima be opened up to new, more intense, experiences of sexual exploration and growth, before I would once more be allowed to feel the caresses of a loving male partner.

Part 2 - Naughty Show-Off Jemima

Eventually, I started going on the internet (as one does) and seeing if there were any decent men out there who might possibly be interested in me.

There seemed to be plenty of submissive girls but not that many potential suitors, apart from professionals. I didn't want to be dominated by stern women or sadistic 'tops', I wanted to be a proper girlfriend to some nice, intelligent guy who would fancy the pants off me (...often...).

When it came down to it, it was nothing ventured, nothing gained, so I decided to take a chance and reveal myself in public, in a limited, controlled, manner. After much agonising I reckoned that my very favourite French Maid outfit, actually purchased on the web, would best fit the image I wanted to portray - light and frothy, sexy and girly, without being immediately explicit or over-heavy...

The main item of the costume was a halter-neck apron consisting of a black satin heart-shaped piece, just wide enough to cover both my nipples, attached to the high waistband of a perky little backless black skirt, with a cute pocket made from a matching lace-edged heart, and tying at the back with a big satin black ribbon. All the edges of the garment were trimmed with flounces and flounces of soft white lace. Full, frill-backed black panties, white lace cuffs and a cute little lace cap completed the uniform. I decided to team these with a pair of sheer black thigh-length stay-ups, with stocking-tops of black lace decorated with white heart motifs, and my faithful white leather strappy stilettoes.

I had such fun taking the photos! The idea that I was going to let total strangers see them excited me greatly!

I took a frontal shot, with me holding the little skirt in a curtsy, then a shot from the rear, looking cutely back over my shoulder, cutely showing off the gorgeous frilled panties. Finally I took a naughty side shot, with me bending slightly forwards, panties down around my knees, stiff prick poking up from under the short apron skirt. My right hand stretched out behind me holding the feather duster temptingly suspended above my bare bum.

I was quite proud of the way the last one turned out: surely there was at least one decent, red-blooded male out there who fancied the idea of making me feel his lovely hard prick pressing between those soft white cheeks? Someone who'd like to woo me, talk to me, share his thoughts and passions with me before bending me over and plunging himself inside the warm, welcoming place that lay secretly waiting for him? To be even more obvious, I made the caption on this one read "Naughty Jemima requires a real man to give her a good, regular, seeing-to!"

I posted the photo set on a couple of the more upmarket tranny sites and carefully invited correspondence...

Part 3 - Is There Anybody Out There?

The response was disappointing, to say the least. Virtually all the replies consisted of banal - verging on sub-human - offers and comments, the spelling and grammar of which were calculated to send any English teacher into the depths of despair. Although some were obviously well-meaning and genuine, it was clear to me that all the more astute TV-fancying hunks were staying well away from the internet! It seemed Jemima was condemned to a life of, literally, pleasing herself.

Then, a couple of months after I'd given up all hope, I received a reply that interested me.

His name was Glenn and he seemed very genuine. An American guy living in the UK, he managed maintenance services (you really couldn't make this stuff up...) for a photocopier plc based in Reading. He appeared intelligent, self-aware, very clear on what he liked and didn't like and consequently what he was looking for. He was heavily into both transvestites and bondage and, I got the impression, had had quite a lot of experience with both. Divorced "ages ago", he seemed like a nice person, sensitive, but with a strong will and well-able to distinguish between role-play fantasies of sexual power over a submissive partner and the world of real life.

Aged 47, he was eighteen years older than me at the time, and this made me unsure at first - after all he was old enough to be my dad, for God's sake! - but deep down I was rather attracted by the idea that such an older, more experienced man, could be interested in me. His outlook was more 'bondage-scene' than I expected to get on with (...although I had no experience, all those straps and rings didn't do that much for me...), but I found myself enjoying and playing-up-to his world... and I just couldn't help speculating what it would be like to endure a little of his discipline, ending up, naturally, with him making wild, passionate love to me... so when he sent an email describing a fantasy scenario about having to chastise his young, prick-teasing girlfriend and how it ended up with him tying her up and having his way with her, I simply just couldn't resist...

His e-mails made me really excited and, a good sign I thought, he could make me laugh too. His photos looked very nice, short dark hair, greying at temples, hazel eyes, clean-shaven, strong jawline, even a little dimple in his right cheek.

Six foot one, 178 lbs, fit and active lifestyle, and best of all: eight inch cock (...an inch bigger than Steve's and TWO whole inches bigger than mine! - it made my stomach flip every time I thought of it..)

I replied detailing some of my fantasies and told him how I had been lucky enough to turn some of them into reality. I encouraged him to elaborate on the bondage and spanking scenarios he enjoyed (...naked on all fours your leash tugs me back onto you, the studs of your cock-ring rub against my arse...) so he wrote more about his exploits, both real and imagined, and - sweetly apologising in case it gave offense - included a marvellous scenario with me as his naughty girlfriend. He wrote about tying me face-down over his office chair, wrists securely bound to knees, and giving me a well-deserved spanking with his leather belt before spinning the chair round and taking my "tied and helpless ass" from behind. Needless to say I was absolutely bowled over, masturbating feverishly as I constantly read and re-read what he would like to do to me... Did I dare take the steps to make it real?

He was amusingly fascinated by my relative youth and inexperience, translating it into his writing with me basically as an naive girly craving 'a bit of rough', desperate to submit herself to some down-to-earth all-American sex and discipline. I didn't discourage this particular line of thought one bit, in fact, in return, I sent him some more photos - much naughtier ones!

One picture was looking down on me from above, kneeling, my little maids cap perched cutely on my uptilted head, looking straight up into the camera. The next was with my glossy red lips parted around the large glans of my flesh-coloured dildo - just as if I were taking the photographers own prick into my mouth. Then there was one with me licking my way down the realistically-veined shaft, and another full face shot, with my long black eyelashes lowered, I'm clearly concentrating on properly sucking the thick seven-inch phallus, my daintily rouged cheek bulging in an effort to encompass its length...

I sent another set, shot from behind, the first with me positioned on hands and knees on the bed, ruffled panties pulled down round my stockinged knees showing off my smooth, round bottom, its soft furrow fully exposing the tight pink rosebud of my anus to the viewer, then five more pictures of me blatantly enjoying the introduction of the now-moistened dildo to my rosebud and sliding it right inside...

If that lot didn't whet his appetite for me, I didn't know what would! I felt incredibly naughty e-mailing such revealing pictures to my new friend, I day-dreamed about him sitting at his computer, opening my files and arranging them all across his desktop; gazing at them while his prick hardens in his jeans, demanding to be released... Quickly unzipping, he would stare at my face, at my luscious open mouth, before grabbing his swelling organ and starting to pump, imagining that he's feeding the poker-stiff shaft between the soft red lips of his sexy femail-pal...

And that was that. Together, we decided on the terms of our joint fantasy encounter:

I would go down to visit him at his home and the meeting would have a strictly observed structure. Glenn was insistent that once we had actually met, I would then be able to make a choice: I could pay a sexual forfeit and earn the right to enjoy his sexual favours, or we could just have dinner and simply enjoy each others company - it would be entirely up to me.

If I chose the forfeit, I would present myself for discipline as Jemima, all made up and dressed in my maids finery. I would be restrained in a manner that he would decide on the day, a vibrator would be inserted into me and switched on, and it must be kept up inside me throughout the duration of the punishment. I would then receive 12 strokes on my naked buttocks with a riding crop - they would be proper strokes, firm enough to hurt, but, since I was a novice in this area, not hard enough to leave marks on my virginal flesh.

If I enjoyed the experience, however, in any future encounters it would be entirely up to me if I wished to surrender myself more fully to his skills with the whip... (..my heart was going like a jackhammer when I read this, what the hell was I doing? Trouble was, this 'Story of O' stuff turned me on me as much as it frightened me...) Once the forfeit was successfully complete, and if I had been a good girl, I would then be instructed on how I was to sexually please him.

A bit scared, but very excited, I agreed my fate with my exciting new admirer.

Part 4 - Hoping to Please a New Lover

So in a nutshell, I crammed my special travel bag full of my maids outfit, Jemima's make-up, shoes and things and hopped on the train to Reading.

Quite a long taxi ride from the station to his house. Nice, tree-lined area, obviously quite wealthy, all the houses having proper long driveways with big gates of wood or wrought iron. I paid the taxi driver and, feeling quite nervous and out-of-place, walked up the path between the well-kept lawns to the large, wisteria-covered 1930's-era house.

The door opened as I reached it and a tall, distinguished but informal-looking man appeared, smiling at my confusion. My heart flipped - the guy I had dreamt and fantasised over constantly for weeks was actually standing right in front of me - and he was gorgeous! He had a real presence, too. Looking back I always remember the friendly twinkle in his eye as he welcomed me, first with a kiss on the lips that had me quite flustered - Steve had only kissed me when I was dressed as Jemima - and then with a much-needed glass of red wine; all at once I knew, whatever was going to happen, Jemima was going to be in for the time of her life.

To break the ice, I was given a tour of the house. Glenn had inherited it from his parents, and was obviously very proud of what he'd done with it. He showed me where the bathrooms were and which bedroom was mine for the weekend. I marvelled at the equipment in his gym room, images of sexy possibilities running riot through my head - maybe one day he would be working out on me in there - and admired the large converted attics, big enough to contain an entire apartment. Although by no means rich, Glenn had obviously not been short of money for quite a while.

We sat in the conservatory and chatted - I was probably a little talkative and over-enthusiastic at first, because of nerves, but he didn't seem to mind, in fact I got the impression that he found it charming. When the second bottle of Tempranillo came out, we were both at ease with each other, and he started discuss exactly what the 'rules' of our encounter were going to be.

I was to present myself at the door to his 'Study' at seven o'clock that evening. There was no pressure, I had all afternoon to think it over or change my mind. If I had decided not to go any further, all I had to do was turn up dressed normally and we would go out to dinner and a few beers. On the other hand, if I arrived dressed and made-up as Jemima, (...one girly ready to accept her punishment, Headmaster...) then it meant that I had decided to accept the forfeit and agreed to submit myself to his scenario. In the latter case, however, dinner would have to be off the menu; I would only be allowed to eat whatever Glenn wished to feed me...

There really was no decision to make! At about a quarter to six, I ran a bath, went for a soak, shaved my legs, trimmed my pubes into their usual heart-shape and gave myself a REALLY thorough clean - outside and in, if you know what I mean. Cream massaged into legs and arms, a dash of perfume on wrists and throat - not to forget between my smooth white bottom-cheeks... Afterwards, feeling quite relaxed and happy under the circumstances, I floated into my room and started to get changed.

God, there's nothing like putting on stockings and stepping into a pair of high-heeled women's shoes. Every girl that has done this will really know what I mean... Whatever it tugs on, deep in my heart and groin, it never fails to work, never fails to make me virtually swoon with pleasure. The coolness of the hose before it's warmed by the at of your flesh. Sliding sheer stockinged toes into the smooth curves of the shoe, fastening delicate straps above trim, exposed ankles, then standing to find your balance, your weight flowing straight down onto the tips of your toes, you feel almost weightless, transformed by four inches of slender pointing elegance beneath each long arched heel. The backs of your calves pull up tight, all the way up to your pert, pushed-out, behind, their new poised length showing off every heightened curve, every taut muscle beneath their black nylon patina... sheer heaven every time!

Jemima is reborn again, in her true image, adorning her body to display to the world what she truly is: supremely sexual, provocative, erotically welcoming and filled with the desire to exult in her femininity with a caring, reciprocating, male lover.

Nestled within my carefully shaved, heart-shaped pubes, framed above full lace stocking-tops, my prick is as stiff as a board and flushed with excitement. It has been so long since I enjoyed the marvellous anticipatory thrill of knowing that soon I was going to be with another man. I hope he will like me. Moreover, I hope he will want me, want me enough to let me express my need to give him all the enjoyment and pleasure I can offer.

Time to put the black satin panties on, pulling them up full and tight, the white horizontal frills running charmingly across the shapely curves of my bum. My prick is deliciously stiff, snug beneath soft, enveloping, satin.

I sit at the bench in front of the vanity unit, the feeling of the soft padding of the bench under my bare thighs gives me yet another reason to be glad I'm a girl. I apply my make-up for this evening as instructed, minimal and light, apart from eyeshadow in deep blue shading to almost white, dark, luscious lashes and glossy red, wet-look lipstick. Following my specific orders for the evening, and feeling deliciously sluttish, I also apply copious amounts of lipstick to each of my stiff and eager nipples.

Hair back in a simple ponytail (...don't want it catching in my mouth at any crucial moments, do we...) and simple gold loops for my ears.

To finish the outfit, I put on my apron. Pushing my head through the opening, I tie the ribbon at the back of my waist with a big lacy bow.

Pinning the perky little cap to the top of my hair, I slide the frilled, elasticated cuffs around my wrists and Maid Jemima is ready to serve her new master.

I paused to admire the effect in the mirror on the bedside table: what would jump out at Glenn when he first saw me, in the flesh? - Would it be my pouty and kissable red lips... - or the swelling promise of my naked breasts peeking out from beneath their heart-shaped satin covering... - perhaps his eyes would be drawn to my upthrust and curvaceous bum artfully displayed by the backless apron... - or maybe he would enjoy my bare white thighs smoothly descending to long nylon-sheathed limbs and delicate white stiletto heels?

My naughty, excited mind started to wander; would I make him hard when he saw me? Would his cock be as nice as it looked in the photos? Would he let me taste it? I left the room before my heartbeat went into overload...

Part 5 - An Entrance to Remember.

The lights are dimmed in the warm room, the numerous rows of bookshelves lining the walls blending into shadow. I immediately notice the real fire - something I love - the smell of the woodsmoke drifting cosily through the air. Most of the furniture seemed to have been pushed back, away from the center of the room, to make space for something on the floor.

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