tagTranssexuals & CrossdressersWeekend with Elaine Ch. 01

Weekend with Elaine Ch. 01


Well, a very nice surprise has come along. A very old girlfriend has invited me over to her place in Norfolk for "an interesting very long weekend" in 10 days time. Instructions are to follow. The last time that we spent together was more than interesting and definitely explored some new experiences for me, and also for her. And it is some of this that I will share with you here.

Elaine and I have known each other since University days. We went out with each other for a few years but didn't get around to marrying, though it did come close. We would probably have separated anyway, but our lives have certainly been interesting in between times and in how we have developed.

Elaine is very close in age to me (being the same year at Uni) but she still retains her looks and size from those days, perhaps a little fairer in her hair than the brown she used to be and a little more around her bottom. She's 5ft 4 tall, a size 4 to 6, small breasts (34 small B), pert nipples and a lovely little bottom.

We met in our first year and were soon like rabbits at each other, and we both thoroughly enjoyed exploring sex together. My cross-dressing didn't feature particularly highly in the mix, partly with the size difference, and I guess just the phase of life, even allowing for my previous experiences in this area.

Apart from being very good friends and going everywhere together, we had a lot of fun and sexually, Elaine was very much into giving oral, being oralled, watersports (not so much my cup of tea), anal sex, toys, and we had explored some aspects of restraint and the dom/sub scene. We also had sex in a number of slightly more unusual places than the normal, such as in a car park near Loch Lomond in full view, though it was raing; so I guess there was an element of exhibitionism in her mixt. We hadn't reached the stage of actively exploring our bisexuality; that was to come later; we did though fantasize of such scenarios.

As to the intervening years, we had kept in regular contact by letter then e-mails and the occasional call. Elaine married, went off to Suffolk, had her family at a fairly young age (now grown up) and was involved as a director a substantial company. She divorced before I did and I was one of her confidantes to bounce things of. And she was highly supportive of me when my turn came around.

We hadn't met for a number of years, but as I came out of the whole affair, our e-mails got a little more sexual in nature and 'exciting' as we shared our interests and fetishes together. All of this has led to us meeting up occasionally for a weekend involving good food, walks and a lot of sex. This has been mainly on her terms so up to the weekend I am to describe, she hadn't seen me fully dressed or never played with a gurl.

Sexually, Elaine is great; she is very fit, knows what she wants and enjoys, and very open. She enjoys sex for sex's sake rather than romance though she has one. I know that she has had a few 3-ways and that she is still into all the activities I described above but now she is happy with a woman, though her preference is men. She loves masturbation and has a substantial number of toys; I have added a few to her collection and I too have ones that we have shared.

I said that Elaine is very fit. She loves prolonged sex sessions and getting very open and wet. She has amazing kegels and several times we have 'knotted' together with Elaine on top as my cock remains hard in her cunt and we verbally share our fantasies and thoughts.

She loves being taken in either her cunt or her arse and enjoys having a vibrator in there as well as feeling me in her other hole. She does have (to that point in time) an unsatisfied desire for double penetration and also for experiencing a massive cock at some point. Her kegels are such that she can manipulate a cock to the top inner are of her vagina and also to be able to pull off some interesting fucking by lowering herself up and down on a cock so as to literally frig herself to an orgasm. Her cum is fairly heavy and both her clitoral and vaginal orgasms are pretty intense. Taste-wise and aroma-wise she is not that intense as some girls that I have known, but she is always pretty wet and can 'seriously orgasm' when really turned on.

So a final description, a lovely nice cunt, not that heavily pubed, more of a natural strip. A well defined labial area and a nice protruding clit when it is erect, and a lovely puckered anus, devoid of any hair.

She is always lively company and has a lot of interests from cooking to horses and various sports. Her dress sense is fairly conservative being an English countryside girl and she has never been one for exotic underwear or lingerie. And, as far as I have known over the years, she has always preferred female jams over a nightie.

We e-mail each other about 5 times a week; most of it is irrelevant to this experience but the salient point is that obviously I get to hear some of what she has been up to sexually and the same is true the other way, and especially when we are feeling frustrated or whatever.

In mid January, I got a 'sounder' of whether I would be up for a long weekend at the end of February and that this would be at her house, rather than the previous time when we met up at a lovely little country inn in the Peak District. I responded with a yes, and nothing really was said until early March when I received a small parcel with a letter in it from Elaine; her writing is pretty distinctive in style so when it arrived, I knew it was from her.

I opened it up to read the title "You are to be my Sexual Servant for the W/End of March..." and Dear Clare (she knows my name and a lot of my experiences in this area as well as my want to become increasingly feminised even to the point of surrendering my male life to the right woman or man). She reiterated the invitation and the date and then "if you accept, by e-mail please, then you will spend the whole time with me as Clare."

"As you know, I have never seen you dressed and when I do, I want to see what you can achieve and not allow (my name) to interfere. Therefore acceptance of this invitation will entail the following:

* The whole weekend to be spent dressed as a woman. You will arrive as a woman and leave as a woman.

* I will treat you to food, wine and other things as you have covered the previous two weekends. There are some things below that you may need to buy or arrange beforehand.

* That you will be my sexual servant and that I will use you in whatever way I see fit. You will not engage yourself sexually with anyone else between now and our time together and you must refrain from self-relief for a minimum of 5 days beforehand. I will not put you in compromising situations that I am uncomfortable with, but I may decide to push your/our limits.

To this end you will:

(i) Arrive only in women's clothing and shoes. You may wear unisex clothing, but it must be of a female brand; however, I would prefer you to be as feminine in your dress as possible. You should also carry a handbag of your choice. I would prefer that you arrive by rail as this will mean that you have to travel in public and cross London as a woman. I would suggest arriving in Cambridge on the xxxx (mid pm) train from Kings Cross.

(ii) You will carry no men's attributes in your luggage, other than shaving gear. Even your deodorant and other items must all be female. I'll have the requisites in to make sure your pussy and my pleasure tunnels are clean.

(iii) You should be fully prepared as to smoothness of your skin, and your nails (both feet and hands) should be manicured and done. You should obviously do the most you can with your hair. You will wear your breasts and these should have been fixed so as not to come off for the weekend. I am looking forward to seeing and feeling them.

(iv) You should have your clothing for leaving and your time here. For here, I would suggest a couple of skirts for evenings, appropriate tops and shoes, and possibly some wool one pieces and leggings as it is still cold. However, you must bring a black silk blouse, preferably with a frilly or Peter Pan collar and also the following dress. (Here there was a picture and an outlet in my town that stocked it; I'll leave the details for later)

(v) A minimum of three pairs of stockings, preferably Wolford, two black or charcoal, two pairs of tights (one ribbed and in black).

(vi) All lingerie to be in white, pink or cream. At least two bras will be underwired and two soft to give me a selection choice, also include one sports bra (and I would suggest matching panties), one matching set to include suspender belt or a waspie. Two silky nighties, one long and one medium length. I also want you to source a pair of white/off white/skin-tone panties like I used to wear at University and that you enjoyed feeling me under my skirt. M&S carry something very similar. (Elaine used to like to wear these slightly shiny satiny feel briefs and I enjoyed getting my hand under her skirt and feeling her bottom and sometimes cunt, and often in public such as flicking the back of her skirt up and 'going in'.)

(vii) Bring at least three vibrators, including my favourite black butt plug one (this is about 6 inches long and like a series of rings). Two should be chrome or glass, as I only want to use heavier toys in our pussies.

(viii) I want you to mail me a cutting of your hair. Soonest please.

(ix) Open the small parcel and wear it during the whole trip.

Please send back your acceptance of this invitation and conditions by e-mail.

I opened the envelope and inside was a small present and inside that, a gold chain necklace. On it, to go across the nape of my neck, was a large gold and amber bead and joined up gold lettering spelling "I am Elaine's"

I admit that time couldn't pass fast enough. Most of the items I had but some shopping was needed and obviously for this dress that she had seen and it was very different to what I normally wore.

The evening before I packed and prepared myself, having also had a salon visit for my nails and some waxing. I duly fixed my silicons on, this time, just about a full B small C cup. I didn't sleep that well with the anticipation of what was to come.

Next morning I showered, shaved, made up (lightly) and breakfasted. For my lingerie, as per instructions I decided to go for a fairly plain white bra that had a small white cross just under the cup join and this was matched through my white hi-brief panties where the cross was at the front top, and to wear tan pantyhose.

For my clothing, I went for a cream Massimo Dutti silk blouse with a rounded collar, a pair of Kookai caramel chamois-like pants, and then a muted fuchsia cashmere sweater with a drop neckline that revealed the top of my blouse, my chain and down to my breasts. Shoes were low heeled (I guess about 1 and a half inch) leather sandals by Banana Republic to match my outfit. I wore a couple of bangles and a ring that I had found at Topshop, so nothing expensive but they looked good. My handbag was a tan Radley bag, nice and spacious for those little accessories and wallet, phone etc. I didn't forget the necklace and that was last on.

On with my coat (as it was still pretty cold) and I went for a dark grey one with a slight sheen I have and a (faux) toned light brown fur lining down the edges, sleeve cuffs and hem of the coat.

I had a taxi take me to the station, onto the train and then into London Paddington and another tax over to Kings Cross. I admit to feeling exposed as this was the first time I had travelled by public transport but I didn't sense any overt glaring which I guess is, firstly,a testimony to what level I can achieve and, secondly, by dressing nicely and conservatively and to the environment you are in (and the same for make-up), you draw less attention. I even ventured forth for some refreshments from the M and S store.

So all this was fairly non-eventful and I arrived in Cambridge a couple of minutes late and came out of the station to look for Elaine. She was there but she did do a double take when she saw me, despite having seen photos of me completely dressed up in the past. She came across with a huge smile and we swapped a cheek to cheek kiss.

"Wow, oh wow," was her reaction.

We headed to the car, dropped in the luggage and jumped in, only to go a short distance to park up just off the main street. This was to get some tea and have a chat, and then Elaine wanted to go shopping for something for me that she had found so I had to do the try on for sizes.....more on this later.

She couldn't get over how I looked in the flesh and the 'deception' that I could pull. As she said, the only thing I had to watch was voice tone and a little on walking gait (to get my legs even a little more in front of each other so there was more wiggle behind), but my shape (especially my bottom), hands and (lack of) adams apple were all pretty good.

From shopping we walked down the street and then into a commercial yard and into a salon.

As we entered, Elaine said to me "Here's your first surprise for the days with me. I have arranged for you to have hair extensions and that will help you look even more convincing than you already are, hence why I needed a cutting of your hair. Jenny is an old friend of mine and I have told her a lot about you."

Jenny met us and led us through the salon to the back. I sat down and she went to work firstly wetting my hair and then she set in to place eight pieces of 16 inch real hair that was an amazing match in colour and held a slight curl to it all. This was a first time for me with real feminine hair and I loved it.

Conversation was between the three of us, with a glass of white wine at hand, and largely about my experiences and also hair care (not to be too hard in washing it) and in brushing it. Elaine said that she would help brush it out to get me on the right path; (Elaine's own hair is more of a "fluffed up" bob style.)

At the end of it all, I had to twirl and get the feel of it and the sensation of hair down to my breast line and extended over my ears was tremendous.

"We should get your ears pierced, so you can wear a lot more than you do with clips."

I was wearing simple gold clips by the way, but these were now largely covered by my new style, which was best swept right to left and particularly sexy when over my left shoulder. I gave them each a big hug and a kiss,

We headed back to Elaine's village, some 30 minutes away on the Norfolk/ Cambridgeshire/Suffolk border. Her house is a large old cottage, detached, in some nice gardens, and has 5ood-sized bedrooms including her lovely feminine master bedroom.

I have stayed there a number of times in the past 2 years, so I know the layout and where things are. We pulled in and unloaded the luggage and bags and having done that, Elaine came across and gave me a long lingering kiss, her tongue to my mouth.

We opened a bottle of NZ wine and poured a couple of large glasses and I answered a range of questions that she had about my dressing. I had to describe the salon, also fixing on my boobs, and how I felt. I also tried teasing out of her weekend plans but she was pretty evasive about them.

We then headed upstairs to Elaine's bedroom as she wanted to "inspect that I had met her conditions" – which I had duly fulfilled. She proposed that we would have a quiet evening and that I probably wanted a shower and to change out of my travel wear. We would head out to eat at a local pub restaurant, within walking distance of the house, so we could both have a few glasses of wine. She would unpack my clothes while I was in the bathroom and lay out what she wanted me to wear.

So off to the bathroom I went and peeled off my clothes, hose and bra/panties and took a nice short shower (with a shower hat on to protect my extensions.

It was amazing showering my naked, hairless, body, knowing that I had such long hair. Elaine had always enjoyed a naked mons pubis and we used to shave each other at University.

Shower finished and toweled off, a touch of make up and lipstick and it was back into the master bedroom, naked in a bathrobe with my hair hanging down.

Elaine had already gone downstairs but she had lain out on the bed what I was to wear. This comprised of one of the soft white bras and the "university" satiny full brief French style white panties, the black ribbed hose, the black Peter Pan collared blouse, and then something I hadn't seen before which was a very, very short plait tartan style (green and black) skirt. This turned out to be her daughter's (who wasn't petite at about a size 14). Then my black 'muletto' heels that I had brought with me and a black long cardigan (not mine).

I slipped on the soft bra and immediately felt more exposed as it meant my breasts had more move to bounce around. I went to put on the panties which soon had my boy-clit going hard at the memories of these wonderful items on Elaine all those years ago.

And then the blouse, the hose and finally the skirt; this gave me the feeling of being hugely exposed underneath and that I would have to be very careful with my legs, though I did have the advantage of having the ribbed pantyhose on as it was pretty cold outside.

I lightly brushed out my hair and brought it over my shoulder so it hung down onto my left breast, and then some perfume. I grabbed a black bag I had and I headed down to find Elaine had changed into a similar short skirt and ribbed hose, with a green blouse and jacket on.

She gave a deep smile when she saw me and passed me another long kiss, taking advantage to slip her hand under my skirt and into my hose to feel my panties on my bottom.

"Very nice indeed," she purred through her lips, "But later, let's go and eat." We put on coats and headed out into the cold air, arm in arm, down to this local pub/restaurant.

Dinner was fun and we had some good wine and we didn't have to drive! We had a nice quiet table and were able to gently tease each other. This had been the norm at other dinners we had had before.

At one dinner, I had Elaine go to the Ladies and insert a vibrator that was then controlled by me, and also a butt plug with a similar control. We had gone for walks after dinner and then coffee with me playing with the sensations and intensity of feel inside her cunt or arse. Another time, I had her insert Ben-Wa balls and then changed them out for a larger pair as we stood on the cab line in front of the Savoy Hotel, one very cold January evening – she was in a fur coat.

This time she turned the tables and after desert she suggested I went to the Ladies and have a pee. I had to pre-prepare myself with this heavy chrome plug that she gave me. Inside the plug was a 'solution' that moved with my movements of my bum.

I came back to the table and Elaine was smiling. We had another coffee (after all we didn't want to fall asleep straight away) and a cognac each. Elaine was whispering to me that she wanted me under her, pleasing her with my tongue and nose.

Elaine settled up the bill and we started to head out, however she had us go by the Ladies which were near to the back door. Inside told me to remove my pantyhose. She took hers off too and we put them in our bags.

"I want you to feel really exposed underneath against the cold air."

So we went out and I must say I felt all but naked as the cold air moved around under my very short skirt. We were walking back when I felt Elaine's hand come under the back of my coat and under my skirt to feel my panties, just as I had done to her to tease her all those years ago.

"Stop and lean over that bench," she ordered.

I did and I could feel the very short skirt ride up on my bottom and my hair was hanging down in front of me. She leant over and kissed me and then came behind me and started to play with my panties, my bottom and to wiggle the plug in me.

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