Just One Of These Days…

She went to her chest of drawers and found a satin bag with a purse string. Then she took me by the hand and led me to the en-suite bathroom, which was spacious, with a tub and a walk-in shower.

She turned on the shower, checked the temperature with her hand, and led me under the water. We embraced and kissed deeply, tongues playing, while the water flowed over our bodies, our cocks both at half-mast, touching each other.

Janine took some shampoo and washed my hair. She then took some shaving gel and started to shave my chest. As I am naturally not very hairy and the little body hair I have is light in colour, the procedure didn't require much effort.

Janine said: "You have a beautiful body, Honey. Let me prepare you, I can't wait to dress you up!"

She told me to put my foot on a little plastic step, and lathered and shaved my legs. She looked into my eyes and whispered: "I'd like to shave your pubes and bum, will you allow me...?"

I just nodded, she gave me a big, bright smile and went to work.

When she finished shaving me, she made me step out from under the water, produced some hair removal lotion, and put it gently all over my cock, balls, perineum and ass. I felt my cock twitching when her fingers lightly touched my anus to spread the lotion.

"We'll have to let this work for a few minutes." she said, put her arms around me and started to kiss me again.

After a few minutes of making out we stepped back under the shower and she gently washed my body with some almond shower oil. After rinsing off, my body was smooth and hairless. She got her little purse-string bag and gave it to me.

"Have a look inside. There's one for me, and one for you if you want it. I occasionalIy wear one when I'm dressed, and I like the feeling, particularly when I walk. I find them quite sexy!"

I looked at her questioningly, opened the purse string and found two butt plugs and a small tube of lubricant. Both plugs had jewelled bases, one dark red, one dark blue. I felt my cock twitching again.

We looked at each other and I said: "I have no experience with these, but if you say they're nice and you would like me to try one, then I trust you. And you're right, they do look sexy!"

I got another big bright smile and under the running shower she embraced me again, reached behind me and used the almond shower oil to gently and slowly wash my anus while looking into my eyes and kissing me. I then felt her reach for the little tube with lubricant. The next thing was her finger spreading some cool gel on my anus. She kissed me with her tongue swirling when I felt her finger parting my sphincter, spreading the lube inside me.

I let off a hoarse moan and she said: Relax, Honey...this is supposed to be pleasure...do you want me to stop?"

I whispered: "Don't you dare...this feels really sexy. It's just new to me, I never felt anything like this before..."

She continued kissing me while lubricating my anus, and before too long she added a second finger, slowly moving in and out. All I felt was pleasure. I sighed and moaned. Our tongues danced.

After a while she removed her fingers, washed them and stepped out of the shower to get something from the cabinet. She came back carrying a bulb with a 3 inch nozzle about the size of her finger.

" I use this to cleanse myself before I play with my plug. It's called an anal douche. Are you okay to give it a try, Honey...?"

I whispered: "I'm all yours, Janine...I'm in your hands...you can do anything to me..."

This made her laugh, and she removed the nozzle to fill up the bulb with warm water. She put the nozzle back on and lubricated it, then embraced me again with a lubricated finger searching and finding my anus again. Again, only pleasure, as she moved in and out, then added a second finger. I felt her fingers being replaced by the nozzle. She slowly squeezed the bulb and I felt the warm water entering my anal cavity. She gently pulled the nozzle out and told me to squeeze and keep the water inside me for a few minutes.

After a couple of minutes she told me to sit on the toilet and push.

After ejecting her little present I cleaned myself and she repeated the procedure, all the while showering me with kisses.

Finally, only clean liquid came back when I pushed. She lubricated her fingers and the red jewelled butt plug, put her arms around me and I felt her fingers play with my anus again. She again asked me to relax and I felt the butt plug parting my sphincter. The plug was more substantial than Janine's fingers but she had lubricated it generously and I felt no pain as it popped into my rear hole and my sphincter closed around it.

"It feels incredibly erotic when you play with my ass, baby. This is soo sexy...you have the greatest ideas, Janine..." I groaned.

"...and now it's your turn to get to work." She whispered.

She re-filled and lubricated the anal douche and had me slowly inserting it in her anus, gently squeezing the bulb.

It didn't take as long for her to get clean, she must have had prepared herself before I arrived.

When she was clean, I had her bend over slightly, asked her to put one foot on the little stool and knelt down behind her. I looked at her exposed pink puckered anal star and couldn't help starting to kiss her smooth ass cheeks, slowly moving towards her crack. Her pink hole looked very pretty, and when I kissed and ran my tongue over it she let off a little squeak. I gently pulled her ass cheeks apart and continued to gently lick her anus. Long sighs and moans came from her.

"Oooh honey...the things you do with your tongue...I've never felt anything like this...your tongue feels soo good...nobody has ever done this to me..."

I stiffened my tongue and penetrated her anus, licking her clean insides. A louder squeak. More moans. Some unintelligible babbling. She clearly enjoyed herself and I loved servicing her this way. This was a first for me, but I felt no repulsion, only the love and pleasure to make this gorgeous person feel special.

I finally put some lube on my finger and slowly slipped it into her glistening hole. She was totally relaxed and there was no resistance. Like she had done, I added a second finger after a while, and when she was thoroughly lubed, I took the butt plug with the blue jewelled base and gently inserted it, watching her sphincter close around it. This was greeted with a long, low moan. I was very aware of my butt plug and was happy to reciprocate the feeling.

"Oh my god, Honey...this is heavenly! I think I love you!"

We cleaned any surplus lube from each other and kissed again. Tongues playing, we reached around and rocked and moved each others butt plug, moaning into our mouths while kissing, our cocks touching and hardening.

She took my hand, led me to the bedroom and said: "We wont be able to fit either of us in a dress with an erection..."

She laid on the bed and rolled to her side facing me, pulled me close and started licking my mushroom head, then closed her lips around my cock. I gently pulled back and laid down next to her facing her cock, and we started a slow 69 with our hands again moving our butt-plugs in and out.

The double stimulation had us climax very quickly and Janine came first, her come flooding my mouth pushing me over the edge. I kept some of Janine's come in my mouth and sat up. She must have had the same idea, because when she sat up and we kissed I found she had kept some of my semen in her mouth. Our tongues exchanged each others fluids and eventually we both swallowed.

"That was lovely, Honey." Janine said, looking at me with big brown eyes. "Now, can I get your nails and hair done...?"

I nodded and she carefully, as she was aware I was wearing a butt plug for the first time, sat me down in an armchair.

She pulled up a footstool and sat down, equally carefully. She produced a nail set and lifted my right leg, with my foot resting in her lap. She went to work with an emery board, telling me: "We need to smoothen your nails, otherwise you might snag your nylons, baby."

She repeated the procedure on my other foot and soon everything looked to her satisfaction. She then showed me three bottles with nail polish, one bright red, one dark red and one called black cherry, and asked me to choose. I opted for the dark red, and she started to paint my toe nails.

She looked beautiful as she was working, concentrating on the task in hand. When she was done and my toenails were drying, she went on to work on my fingernails. Once shaped and painted the same dark red shade, she kissed me and said: "Your nails look very pretty, let me start on your hair now."

She did her magic with my hair, and eventually told me: "This is a Japanese hairstyle called a 'Messy Cropped Bob'. It looks lovely on you and goes really well with your facial features. Have a look in the mirror."

The name made me laugh, but when I looked in the mirror, I was completely bowled over. A very attractive young woman looked at me!

"Wow, Janine! This is pure magic! I hardly recognise myself..."

"Wait 'till I get some make-up on you!" She said with a big smile.

"How do you know all these things?" I asked, "you're a real artist."

"You know my mum. She's French, and style is her middle name. She was a lecturer in French literature and she taught me a lot. That includes hair styling and make-up. She sometimes used me as model to try some hair styles or make-up styles.

I quite liked it and always went along. She asked me to keep my hair fairly long, and I still keep it that way. She knows I like to dress up, and she's absolutely cool about it. She used to test shorter hair styles on my dad, who found it funny but never objected. I think he quite enjoyed it as well.

I'd met Janine's mother many times, since I was a kid. She now was in her fifties, always very loving with her son, and she treated me as her son's best friend with great affection. She dressed with great taste and style, always in suits, wearing expensive nylons and heels.

I had always greatly enjoyed the time we spent together, talking and laughing a lot. I could imagine it must have been fun to model for her.

Janine continued putting some light make-up first on me, then on herself. She used a dark red lipstick colour on me, similar to the shade of my nails, and a brighter shade for herself. I couldn't believe my eyes when I looked in the mirror.

"This is fantastic." was all I could get out.

"Let's get you dressed!" she said with a wink, licking her lips. "Luckily we're the same size, so you'll fit in my clothes."

She padded to her wardrobe and came back with a lacy set of knickers, bra and suspender belt in a burgundy colour.

Before I knew, she wrapped the suspender belt around my waist and fastened it at the front, then pulling it around so clasp was at my back.

She asked me to put my arms through the shoulder straps of the AA cup bra and fastened it at the back. The feeling of the diaphanous fabric on my nipples was very special.

She looked at me approvingly, smiled, and said: "Nylons next, knickers and heels after."

Janine went over, still completely naked and giving me a glimpse of her butt plug, to the chest of drawers. She came back and showed me three packs of French nylon stockings.

Capri 7 Denier, the package stated. Chocolate, Cappuccino or Tan.

"Which colour do you want, and which do you want me to wear, Honey?"

I chose Tan for her and Cappuccino, a light brown shade, for myself. She smiled at me: "I'll be enjoying wearing these for you, my love! Now sit down on the bed, lift your leg and point your toe."

She opened the pack of cappuccino-coloured nylons, carefully stretched and gathered a stocking and wrapped my foot in nylon. She slowly pulled the stocking up my leg, smoothing it with both hands. She repeated this with the other stocking, then told me to stand up. She showed me how to clip the nylons to the suspender belt.

Wearing the nylons and feeling the tug of the suspender straps, as well as having my gorgeous Janine dressing me up, made my head spin with pleasure and lust. I grabbed her and we fell in a deep kiss, tongues exploring. Despite having come in Janine's beautiful mouth only a short time ago, I felt my cock stirring.

She asked me to step into the burgundy lace knickers and pulled them up my legs. Slipping them up my nyloned legs gave me little pangs of pleasure.

Janine sat me back on the bed and found a pair of black dress sandals with a 3 inch heel. She slipped them on my feet and fastened the ankle strap. I couldn't help but admire my dark red painted toenails through the nylons.

I walked up and down the room to try and get a feel of walking in 3 inch heels, and found it to be not much of a problem. In fact, I enjoyed the feeling in my calves, the pulling of my suspender straps, the swishing of my nylons against each other, and the feeling of the butt plug rocking when I walked.

This was all new to me, all very erotic, and I very much enjoyed it. I told Janine, and she looked over the moon about it.

"Oh Honey, I'm so happy you're enjoying this. I was so worried and now I've found a beautiful partner to explore these things together."

"Janine, I'm enjoying all this more than you know. I never knew I could feel like this. You've opened a whole new world to me. I love you, baby!"

Janine smiled happily and continued to open new worlds. A dark red lace shift dress with a V-neck and short sleeves appeared and she put it over my head, being mindful of my hair. The dress fell over my body, ending just above my knee.

Again, I walked up and down the room in my heels, and the feel of the dress, my nylons and the heels was incredibly joyful.

"There's a full length mirror on the inside of the wardrobe door, Honey. Go, have a look. You look a million dollars! I was optimistic that I'd be able to turn you in a lovely woman, but you've surpassed all my expectations. I am so very much falling in love with you..."

With some trepidation, I opened the wardrobe door and stepped in front of the mirror. My jaw dropped.

A beautiful young woman in a stylish dark red lace dress looked at me, her calves accentuated by heels and light brown nylons, her red painted toenails, looking very pretty through her nylons, peeping through high-heeled sandals.

Lovely, slightly messy hairstyle. Soft facial features with make-up somehow creating a faintly far eastern appearance. Red lips, the same shade as nails and dress.

I felt a little strange, my brain was trying to process, that the gorgeous creature in the mirror was really me, and I told Janine.

"I know," she said, "it's a little weird the first time you see yourself in a mirror and hardly recognise the person. But the weirdness goes away, the pleasure of seeing yourself dressed remains.

You look absolutely fantastic, Honey!

How's about you sit down in the armchair and watch me getting dressed...? I think I'd get a real kick out of that. It will feel a little bit like I'm performing for you!"

Her eyes shone and she licked her lips. Naked as she was, she put her arms around me and kissed me, her tongue playing with mine.

I sat down and she got herself a black lace set of bra, knickers and suspender belt. She wrapped the suspender belt around her waist, stepped in front of me, turned around and had me fastening it.

She fastened her bra at the front, turned it, then put her arms through the shoulder straps and adjusted the AA lace cups over her nipples. Then she showed me the packet with the nylons I had chosen for her. French, 7 denier, Tan.

I unwrapped the stockings and handed them to her. She sat on the bed, lifted her leg, pointed her toe and slipped her toes with bright painted nails into the nylon. She carefully pulled the stocking up her leg until the dark brown welt came to rest high on her thigh, then smoothed the nylon running both her hands from her foot up her leg. She fastened the front suspender clip, then stood up and with a vey sexy turn of her body, fastened the rear strap. She looked at me, winked, and repeated the procedure with the other stocking.

There is really nothing more erotic than watching a beautiful woman putting on her nylons, and clearly enjoying it.

I told her and she just smiled: "Oh, thank you Honey, that's a real compliment. And watching you slipping into nylons and heels for the first time was quite a turn-on for me, as well. How does it feel now...?"

I crossed my legs, my light brown nylons swishing against each other, and said:

"Incredibly pleasurable and feminine, is the only way I can describe it, Janine. Exciting. I love the feel of the nylons gliding against each other, the pull of the suspender straps when I walk or sit down. The feeling in my calves wearing high heels. My nipples rubbing on the cups of the bra. And your sweet butt plug rocking inside me enhances it all even more. This is a whole new world of pleasure to me...thank you so much, baby, for showing me. That took real courage!"

She looked at me and whispered: "I want you to make love to me, while we're dressed in lingerie and heels. I can't wait. I'm so horny just thinking about it. I want you to take me anally. I want you to be the first. I want to feel your beautiful cock inside me. Will you take my anal virginity, Honey...? Please...?"

I felt my cock twitching again: "How could I say no to this? But remember, you'll have to return the favour. I want to be your anal virgin as well..."

Our whispered conversation made both of us laugh. Janine padded to her wardrobe and came back with a pair of black peep-toe mules with a 3 inch heel and proceeded to slip her feet into them. I admired her red toenails in tan nylons peeping through the mules.

"I'll have to find a dress now..." she said, and headed back to the wardrobe. She returned with a black wrap dress with rounded neckline and short sleeves, slipped into it and tied it at the front. She attached a red rose silk brooch to her black dress, just below the right collarbone. The dress was knee-length and she looked devastating wearing it.

I told her so, and she gave me her brightest, biggest smile.

(4)

We went to the kitchen, our heels clicking. We prepared a light supper, with some salad, tomatoes, cooked chicken and some French bread. Some French white wine from the Loire region. Neither of us managed to eat much, we were just too excited.

I thoroughly enjoyed being fully dressed as a woman for a first time and was hyperaware of lingerie, nylons, heels and sexy lace dress.

We could't keep our eyes off each other, and soon we decided to clear up our plates and return to the living room, each of us a glass of wine in hand.

We sat next to each other on the big, modern L-shaped sofa and looked in each others eyes. We looked at each other, and for some reason we both started laughing, happily.

She looked so pretty, I put my hand under her chin, lifted her head, and kissed her. Our tongues started to dance and our nyloned legs were gliding against each other. As we hadn't taped ourselves, both our dresses showed a little bump in front, when we separated. We started to giggle uncontrollably, then she took me by the hand and led me to the bedroom.

Janine whispered in my ear: "Honey, you know how you licked my little hole earlier on...? I've never felt anything like it before and it made me so horny it just drove me completely crazy...please, will you do that for me again and gently prepare me for your cock...?

I kissed her again and whispered back: "I can't wait, Janine. I love to give you pleasure. How's about we make tonight the night of our lives? I think we've made a good start of it so far..."

In the bedroom, I untied her wrap dress and she slipped out of it. She went to the dresser and got a tube with cherry scented lube and a damp wash cloth and put it on the bed. She put her arms around me, looked into my eyes and kissed me deeply, her tongue darting. Her hand reached behind me and she unzipped my dress. I let it pool on the floor, stepped out of it, and slipped out of my heels.