Weekend with Elaine Ch. 04

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A weekend away with an old gf - entering her femdom world.
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Part 4 of the 10 part series

Updated 10/13/2022
Created 12/07/2010
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We towelled each other down in large fluffy towels and put robes on. Elaine took a hairdryer and brush to gently dry and shape my hair again. She was very 'mistress-ful' at this! And then she dried her own hair. I cleaned down the shower and tidied up, washed out my plastic underwear, and Elaine went through to the bedroom to clean up there and sort out our wear for the evening.

I came through and Elaine motioned for me to sit down and made me up, using a blended grey to brown mix around my eyes, a pinkish blush complexion to my cheekbones and a pink lipstick (a colour I haven't used much). She made herself up using much browner colours around her eyes and a burnt umber/red for her lips.

When it came to clothing, again Elaine ordered me to help her. We started with a burgundy coloured half-cup bra that pushed her nipples upwards on her small B cup breasts.

As before, she made me pay homage to her by, firstly, kissing the inside of her bra cups and then her nipples. The second item on was essentially a matching waspie and, with this, I had to kiss the small of her back as well as half way down from her tummy button.

The next stage was to kiss each silky charcoal Wolford stocking and her feet, and then to help roll on the stockings and I had to secure it to each suspender (US = garter) and correct the tautness of the strap. Her panties came next; she had selected a matching burgundy tanga and she ordered me to pay homage to them. As before, I had to focus on where her cunt and anus would sit in the panties, before kissing her on those beautiful erotic locations.

As to her clothing for the evening, I helped her into a beige silk blouse from Moschino and a nice green wrap around skirt that would come away with undoing one button. Lastly, out came a pair of strappy dark grey heels, and not forgetting some plain gold jewellery. I did question who was coming for dinner to which her response was "You will see."

Regarding myself, Elaine pulled out my pink 2/3rd cup bra from Barbara; this was soft but under-wired, a little lacy and very feminine -- with thin bra straps. I put it on and fastened the clip, moved it into position, and slid my arms through the straps. It is a lovely fitting bra. I followed this with a matching deep pink suspender belt to which I attached black Wolford lacy stockings.

Elaine then surprised me as I thought she would give me the matching hi-sides, but, no, it wasn't to be. She asked me if I remember buying her tie-side panties and a matching bra in Scotland on her 21st birthday (and that evening I had taken her only anally, until the following morning).

"So here we are, Claire" and there was a pair of soft pink tie-sides with long ribbons which hung down my legs and almost to my stocking tops.

Over this lingerie, Elaine chose my grey one-piece jumper-cum dress. This is a cashmere mix, very soft and hangs off one shoulder, exposing my left bra strap, so the pink would nicely contrast against the grey. The jumper came in around my waist and was short in length, so my bottom was just covered. I would have to take care not to expose my stocking tops and pink pantied crotch, either from the front or behind.

To finish it off, Elaine suggested I wear my graphite muletto heels, gold ear-rings and bangles. Elaine finished my hair by brushing it to fall over my left shoulder. She sprayed me with Van Cleef and Arpels perfume, and also perfumed herself.

"You look really good and I could devour you now and make you my total slave!"

"You also look wonderful and I would love to be under your pussy giving you the subservience you want."

Laughter. "Later, I am sure"

"I love being yours and in your control"

A chuckle again. "We need to get dinner on the go."

"Who is coming for dinner?"

"Just a girlfriend of mine. You will like her"

The conversation continued like this, with gentle teasing and Elaine probing me how far I might go in serving her. Lots of "I'll remember that' or "We will see." Somehow we got a simple dinner of a hot salmon salad, mussels and Belgian fries, and cheese, ready. Also, we opened the wine and prepared the log fires. A glass of sauvignon blanc or two, a number of kisses between us, some wandering hands, and 8pm soon rolled around.

The door bell rang.

"Can you answer it please, Clare?"

I went to the door and opened it to find Jenny standing there.

"Hi" she said, "My goodness, you look fantastic."

She lent over and gave me a kiss to my cheek which I returned. In she came.

"Hi, Elaine, I've brought an overnight bag just in case we have too much to drink"

"Hello, Jenny, just put on the landing, I am sure we will have too much wine and the spare room is already made up."

Just as a reminder, Jenny is the owner of the salon in Cambridge where I had my extensions done; if fact she was the one who had arranged the preparation and colouring on Elaine's request and fixed them onto my hair, to the point one could not tell where my hair ended and the extensions begun. Elaine had given Jenny quite a bit if information about me and, of course, we had the chat in the salon and over a glass of wine. I haven't described Jenny though (part 1 for reference).

Jenny was a little younger than us, and was just 40. She too was divorced and her kid was now at university, like Elaine's children. She too was a business owner and Elaine and she had known each other for about 10 years, having met through their children's school.

Jenny was, I would say, 5ft 7, an inch shorter than myself, but taller than Elaine. She has a 'full body' i.e. a breast size of 38 D with very full breasts that hung down when unsupported. She had a pretty good waist and a nice round bottom and certainly took a large-medium sized panties, like myself.

Her legs had good shape to them, tapering down from her bottom. Her skin was very pale, her hair almost black with hints of brown running through. It came down to just off the nape of her neck and was, naturally, very nicely coiffured. Her eyes were green and very attractive, made up in brown mascara, with a hint of light tones for eye make-up and, finally, dark (probably naturally heavy) eyelashes which were neatly styled. She was/is bright and bubbly. Dress wise, this evening she was in a black jacket with a lovely simple silver silk top that hinted at a lacy bra on underneath, a black wrap skirt with black stockings and heels on. She was wearing pearls as a necklace and earrings and sported a Chanel pearl stranded watch. In summary, elegant and simple. Her perfume was quite sharp and hinted at a Calvin Klein.

In she came and we had a glass of wine and idle chat, more about her day and the children. Jenny ran her fingers through my hair admiring her handiwork. She leant over and gave me a quick kiss.

Dinner was just about ready and all 3 of us helped finish off the final preparations. We went to the candle-lit table, just off the kitchen. I sat at the top of the table between Elaine and Jenny and we duly tucked in, pouring some more wine to accompany the food. Conversation continued in a light frothy vein and from time to time, I felt Elaine's hands touching me or my hand beneath the table. As the wine flowed, conversation got more 'personal' and Jenny asked me a string of questions about being a crossdresser, a transvestite or transsexual, and how far down the spectrum I was and wanted to be. I probably surprised Elaine a little in that, if given a second chance and, with knowing society today, I would certainly considered going the whole way. I definitely would have gone onto hormone therapy to grow my own feminine breasts and nipples and take on more hip curvature, soft skin etc; it is something I have been considering recently. She also started questioning both Elaine and I on our University antics and moved the focus to what had happened more recently, and especially last night and today. Elaine was very open with her, but she did hold my hand on the table. As we went on, there was a lot of hand to hand contact over the table, laughter and the occasional kiss between us, in different combinations.

Cheese and red wine finished, the dishwasher loaded, we opened another bottle and headed through to the lounge, flickering with the firelight and Elaine lit some candles and an aromatic one.

We snuggled down onto a sofa and carried on the chat. Now we were onto what had happened the night before and over the morning. Jenny was enthralled. I was now getting very strong vibes, no I was convinced, that she and Elaine had had some sexual fun together in the past; Elaine had given me no clue of this at all, either in our chats or by e-mails between us, other than referring to a couple of women with whom she had had sex with recently. Her descriptions were more about her sexual acts, interests and how she responded and orgasmed, rather than intricate details of her girlfriends or boyfriends.

Jenny manoeuvred the conversation onto Elaine's background and how she was very open with her bi-sexuality, starting with a lesbian experience she had at school and how she always loved the softness of women. Her comment to me was how ideal I was being an "in-between" so that in some ways I offered a midway solution and this was no doubt one of the things that Elaine loved in me. Elaine grinned.

Elaine replenished our wine glasses.

"Enough of this, I think rather than talking about girl to girl, we should see some and then see what happens."

She turned on the TV and a DVD and the screen flickered on with a film of three way female sex, a DVD apparently made by women. We were all close to each other and now Jenny's hands started to gently explore me as I was next to her.

Jenny then said "I would love to see some live action with you two and especially to see how Clare comes across without her jersey dress on."

Elaine replied, "You can, firstly let me go upstairs and prepare a few things but, Jenny, if you want to start to kiss her, please do so. Remember that Clare has to obey me while she is here in my control so, de facto, she now has my permission to please you as if you were me -- and, of course, I love pleasing you to."

In a flash, some of the 'lines' for the rest of the evening ahead had just been established. I was to be at the behest of both Jenny and Elaine and Elaine was in a sub role to Jenny. Elaine disappeared upstairs.

As she left, Jenny took me in her arms and landed me a kiss, her tongue probing pass my lips to explore my mouth.

"You lovely girl, I could take you right here."

She kissed me deeper, exploring my mouth and then my neck and earlobes.

I responded with my girly passivity to encourage her.

"I want you serving my pussy and I can feel myself getting very wet."

She continued to hug me and kiss me, her hands wandering down to my stockings and stroking my legs, moving so ever slowly northwards to my clit area. I could feel myself swelling with the excitement.

Elaine came downstairs and into the lounge.

She laughed, "Looks like you want to explore Clare, Jenny. I want her too! And you."

"Let's have her take her jumper off."

"No, Elaine, I want you two to undress each other, and then you can help me."

I got up and went across to Elaine who immediately started kissing me.

She whispered, "Remember you are mine, though tonight, you should also obey Jenny. Now, let's get those heels off and then your jumper."

Elaine helped me remove it and slowly turned me around, stroking me seductively for Jenny's pleasure.

"That's lovely lingerie on her and a pretty nice body that she has given that she is a TV, Elaine, and I think we have done a great job with her hair, that really helps the overall femininity. We should get you to wear a vaginal gaffe at some point, Clare, so as to hide that little bulge of your boy-clit."

"What's that?" asked Elaine. "Well, I can source some customised latex mini-briefs that have a beautifully shaped vagina. Her clit even goes into an expandable sheath to hold it tightly all in behind and the end of the sheath is open to serve as a genuine sensitive spot for her and to double as her urethra."

"There's a second nice sheath in front of her penile one, and a little under anatomically, for her to be able to fully take a toy or a hard cock; the model I am thinking of also has a nice reinforced ring in the back to allow access to her anus for play or for her to poop, If her man, or woman with a strap, is over 8 inches or 6 inch in girth as that's the limit of the sheath, then it must be in her rear, that's the downside."

"I can even have Clare's hair matched for sewing in real pubic hair and you can then say how much you want and the style of her 'cunt'. I have already had one made for another transvestite client I have in Cambridge."

With that revelation, Jenny took a swig of wine and said, "Come on lets see you, Elaine."

Elaine stepped out of her shoes. "Help me, Clare" and I unbuttoned her beige silk blouse as she stood there.

"Now kiss my breasts." "My skirt." I undid the button of the wrap-around and Elaine stepped out of the skirt. There we were before Jenny with Elaine in her burgundy bra, waspie with stockings and tanga, and me in my pink lingerie. Elaine started to heavily kiss and pet me.

Jenny came across and gathered Elaine in her arms and kissed her. We helped her out of her shoes and unbutton her silver silk top. Her bra was black and lacy on the edges with wide straps and semi-transparent cups revealing her lovely pendulous boobs and a clear vision of her large oval pink/purplish aureoles, capped by magnificent and already obviously hard succulent nipples.

I noticed that she was a little hairy under armpits, but that it wasn't that unattractive. She too was wearing a black waspie, matching her bra. Jenny was now French kissing Elaine heavily.

She murmured. "Clare, on your knees and undo my skirt and admire my stockings and panties." I got down behind her, found the button on her waist and lowered her skirt. She had on black hi-sides, again a combination of lace edging and semi-transparent material that left little to the imagination.

She had a wonderfully shaped bottom and on seeing her from the front, it was evident that her dark, wiry, pubic hair extended across her mons pubis and nearly to the edges of her panties. I suspected that she had some around her bottom crack too. Very different to Elaine. And I could already scent her strong sex aroma emerging, and also that it was very different and much more direct than the subtle tones of Elaine's.

"Yes, Claire, Jenny murmured, we have been lovers since just before our divorces. I just love fucking Elaine and I really think I prefer women now."

Elaine had brought down the queening box and on separating from Jenny, she put it down in front of the fire.

"Onto the box Clare." "No, Elaine, get her to go and get my bag." "Ok get your chin dildo as well while you are up there, the one we used this afternoon."

I went out of the lounge and up the stairs to retrieve the bag. When I came down with it, Jenny was kissing Elaine. Elaine was out of her bra and Jenny was kissing her breasts. Her hands then moved down to help Elaine out of her panties. Elaine stepped away and Jenny saw she was naked as a baby.

"Elaine, I love it, I have wanted you to do this for ages. What or who convinced you?"

"Well, I was shaving Clare earlier and I had the hots and Mark (Elaine's man friend who I knew was her main male) has been after me do shave myself for a while. And you know there is good reason!"

"Well I love it" and Jenny's finger played along Elaine's slit.

"Tell you what you two, I would have love to have been there to see this pee session and the shaving. You are both naughty, so over the sofa with you both."

Elaine and I positioned ourselves and Jenny pulled a paddle out of her bag.

"Eight smacks each for you," and Jenny started to administer her control of us, four slaps of the paddle each on each cheek. "You are both mine and you will serve me tonight."

"Ok, Clare, you can open my bag and please take out the present on top and open it." I looked in and there was a nicely wrapped present in green paper on the top.

"Before you open it, I know that Elaine worked hard on arranging your extensions and other things for this weekend. She has told me lots about you and passed over a lot of the information, so we have been planning like crazy. And that she has e-mailed you for, especially your sizes".

"I hope you didn't get to quizzical given what we were asking. Anyway, we hope that you will get a lot of pleasure from this and other things this weekend, just as the pleasure we get from you, and that it long may continue."

"Thanks, Jenny and by the way, thanks again, Elaine."

My painted nails opened the gift card. It read, 'We want you as a woman tonight and the rest of this weekend, so a woman you should be. Love Jenny (and Elaine).'

My fingers trembled and I opened the gift-packet which was about 10 inches by 6. Inside, I felt this latex item and unravelled it. Oh, my god, it was the vagina that they had been talking about. I jumped across and hugged them and soon undid my panties ties to get naked and put the 'brief' on, with the aid of a little talc in the pack. It just felt so comfortable as I paraded around.

Elaine commented, "Clare, you are now totally under our orders and firstly you can't use your boy-clit now in your usual way for the next few days. Friction of your clit from a real cock or a toy will be the only way to cum rest of the time you are here. And remember, more than 8 inches or 6 inches of cock or toys and you have to either take care in your frigging or accommodate it behind, not that we have access to such monsters." (Laughter from them both).

"Clare, we want you on the box."

I got down and presented my face upwards. Elaine came across and stood above me, opening her legs to reveal her bare cunt. She lowered herself down towards me, head towards the box, displaying her moist gash and playing with herself. She hovered close to me so that I could really take in her moisture and aroma. She then moved back and sat down on my tummy. Her hand went back to play with my new pussy.

Jenny then swung into position. She stood there with her black panties on, letting me take in the image. Elaine leaned forward to help her take them off, as I watched. What a sight of her heavy, hairy bush and her lips between, hardly showing between her pubes. She too lowered herself onto my mouth with my nose on her fragrant anus. She and Elaine kissed and played with each others breasts as they kissed on top of me, Jenny's gyrations giving me the occasional breath before being engulfed in dampness and her excitement.

This servitude of Jenny's cunt and anus lasted at least 20 minutes before Jenny got off me and Elaine fixed on the spiky black chin dildo. Jenny gave Elaine a double headed dong and Elaine inserted that into my vaginal sheath and climbed onto the other end. As she did that, Jenny lowered herself onto chin dildo and commenced to fuck herself off on me and shortly, this heavy succulent cream emerged into my mouth. As the girls subsided, they kept their pressure on me, Jenny gently grinding her anus into my nose and ordering me to keep tonguing her now very creamy slit.

"Come on, upstairs now."

We went upstairs, bringing the bag with us. Into the bedroom, and Jenny ordered Elaine onto the bed and went into a 69 with her. With Elaine pleasuring her clit, I had to rim her, tonguing her tight puckered love grotto.

Jenny then moved off and let me, lingeringly, kiss Elaine.

She used the time to put on this wide harness belt with a heavily veined 7x5 inch black dildo. She came back to the bed and gently caressed and teased Elaine. Taking my black anal plug that Elaine so loved, she lubed it and slid it into Elaine's rear home. And then she mounted Elaine to fuck her, as I lay between Jenny's rear. This had Elaine coming intensely and once she started to subside, Jenny had me firstly lick Elaine dry and then to focus on the sticky cock. Jenny then had me lie down and went to fuck me (what a feeling) as Elaine put herself over my nose to continually press home on my nose and enjoy my tongue subservience. The friction against my sheath soon had me cumming.

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