Just One Of These Days…

Just One Of These Days...

(1)

I was meeting my close friend Jack for a drink in a bar near my place. Jack lived nearby, and, like our mothers, who had always been close buddies, we both worked at the university, but for different departments.

We grew up together and used to spend time with each other quite regularly. We often went out for a run together, but recently his wife had left him and I had split up with my girlfriend. Because of our personal turmoils we hadn't met in a while, so it was good to catch up.

Jack was about 5 foot 8 and slim without being overly muscular, good looking and very cultured, which was down to his French mother. I'd known him since childhood, and we always had felt at ease in each others presence. He had grown his hair to shoulder length, a little bit longer than mine, and looked well despite the trouble in his personal life.

My appearance was similar to Jack's, about an inch taller and probably a lot less stylish. We'd often been mistaken as brothers.

My girlfriend Millie had left after a protracted period of estrangement. Our interests simply went into different directions, and even sex couldn't compensate for that. And to top it off, she told me that she was more interested in women these days. Luckily, the whole split was amicable and didn't leave any bad mental scars.

Jack's situation was similar, he and his wife just had drifted apart, and finally she had an affair with a female co-worker and moved out, which was met with a degree of polite indifference by Jack.

When I told him that I still regularly went for runs on the promenade and remarked that I never saw him, he appeared to get slightly nervous.

He quietly said: "I saw you only yesterday, Honey. I'm sure you saw me, but you might not have recognised me."

My mum and his mum had always called me "Honey". So did he.

I was puzzled, but then it hit me. I was thunderstruck. The lady! She had looked familiar. She was gorgeous, in a dress, wearing nylons and heels. Make-up. Similar hair style to Jack's.

I whispered: "That was you...!? Wow! You did look familiar, but I'd never have recognised you. Now that you're telling me, it all becomes clear."

Jack blushed, hung his head and said: "I was mortified when I saw you looking at me. I was sure you had made me, and then, you just ran away..."

"That's because I was on a run. And I looked at you because you looked familiar and absolutely striking. Remember, I haven't got a girlfriend. But I didn't recognise you. I still can't believe that was you. You looked fantastic!" I replied.

Jack said: "I was worried coming here to meet you. I was sure you knew and didn't know how you would react."

I quietly said: "Please don't worry, Jack. You've been my best friend for a long time and I love you. I certainly won't be judgmental, just because you like wearing women's clothes. I reckon it's not that uncommon in men.

I actually tried it myself once or twice, when I was with Millie. She was crazy about it and made me dress up."

This seemed to put him a little more at ease.

He lifted his head and asked: "How did you feel, wearing women's clothes? Did it do anything for you?"

"It was strange, I felt sexy and feminine in tights and heels, but as soon as I walked in front of a mirror, it looked wrong. Not garish, but just slightly askew. I could never put my finger on it, what it was, that didn't feel right.

Millie loved it. She used to get dressed up herself and we had great sex. Then she got a career and lost all interest in sex. Sex with men, anyway."

We've had a couple of drinks, and our conversation gave him some confidence.

He said: "I'm incredibly relieved that you're okay with this. You're my oldest and closest friend and I love you. I would have been devastated if you'd been put off."

He lowered his head, breaking eye contact, and quietly said: "Would you like to come on a date with Janine? I think she'd like that..."

His tension was palpable, so I replied:

"Wow! Yes! I'd love to. I'd love to get to know her. Please ask her when, I'll be there!"

"Tomorrow's Friday. How about after you come off work?"

I agreed enthusiastically, and we left, Jack having regained his confidence, even showing a little euphoria.

He hugged me: "Janine will love to get to know you!"

I said: "It will be my privilege and pleasure."

He smiled at me, we said goodnight and went home.

(2)

Throughout Friday I was quite distracted thinking about Janine, and what to wear, and what to bring as present to our date. Mid-afternoon I decided to take back a few hours I was owed and leave.

I went shopping for some flowers, an expensive bottle of Champagne and a box of chocolates. "That should cover pretty much everything..." I thought.

Given I had seen Janine and how stylishly she was dressed, it made me think that I should make an effort and not look my usual slightly dishevelled self. I had made up my mind. I was going to wear suit and tie, something I hadn't done in a while.

When I got home I had a close shave and jumped in the shower to give myself a good scrub. I even put some aftershave on.

I put on a dark single breasted suit with a sky blue shirt and a blue floral silk tie.

I looked in the mirror.

"As passable as you're going to get." I thought to myself.

I took my presents and walked over to Jack's place, a spacious loft conversion he had furnished with great style and taste.

I rang the door bell and after a few moments the door was opened by a beautiful woman in an black and red floral kimono-style dress, with a wide belt tied in a bow at the front, that ended just above her knees. Her legs were wrapped in cinnamon-coloured nylons and she wore dark red high-heeled dress sandals, that made her red toenails through her nylons look very pretty. She had done her hair in a Japanese tousled layered hairstyle and her make-up gave her face a slight far-eastern appearance.

I was speechless. This certainly wasn't Jack. Couldn't be. Could she...?

"Hello, you must be Janine..." I croaked. "You look absolutely breathtaking!"

I handed over my flowers. She blushed and with bright eyes and a smile and said: "Please come in, Honey, and thank you so much for the flowers, they are beautiful."

I entered the large living area of the apartment with its big, L-shaped sofa unit. I handed over champagne and chocolates. After fetching a vase and arranging the flowers in it, Janine asked me to accompany her to the kitchen to open a bottle of champagne she had in a cooler. I could not take my eyes off her beautiful legs in nylons, her calves accentuated by the 4 inch heels, as she walked in front of me.

I poured two glasses of champagne, handed her one and we smiled at each other as we toasted and sipped.

"Thank you so much for coming, Honey." she said quietly.

"This is my first date with a man and my first date dressed up. I never had the nerve to do anything remotely public before you saw me this week, and I was terrified to be recognised by you. But you made it all very easy for me, and I'm forever grateful to you."

She walked up to me kissed me on the cheek. I'm not sure what came over me but I put my hand under her chin, turned her to face me, and kissed her fully on her red lipstick-coated lips. I felt her body slightly stiffen, then relax.

She looked at me with a smile, her eyes shining, and quietly said: "You can come again, Honey!."

We looked at each other, both of us smiling, both of us a little embarrassed. Then we embraced and kissed again, this time deeply, our tongues playing.

Our lips parted and she said: "I'm so sorry, Honey, I don't know what happened there...please, forgive me."

"You are the most beautiful woman I know," I replied, "If anything, I should ask you for forgivenes. Janine, I very much love your kisses and enjoy your company, and would be devastated if it damaged our relationship."

She looked mortified, hanging her head and clearly blaming herself for something. I gently embraced her, lifted her chin and kissed her again. She relaxed and our lips parted to allow our tongues to play.

After a while we looked at each other and she whispered: "Good lord, I only had half a glass of champagne. God knows what might happen if we have more...." and she giggled a little.

With a big smile I said: "How's about finding out...?" and topped up our glasses.

I took the cooler and we made our way to the living room and sat on the sofa. I told her how attractive and sexy she looked in her kimono dress and heels.

She started to gently ask about my experiences in dressing up. We drank some more champagne and I told her: "Millie was somehow into it and asked me whether I'd mind. I didn't, and found it quite intimate and quite a turn-on. Later I started to really enjoy wearing ladies underwear and dresses, I even managed high heels, but I never felt I could quite pull it off the way you do. I always felt like a guy in women's clothes...."

Janine mumbled: "God, I'm so excited, and I'm all dizzy after the champagne on an empty stomach. Maybe we should eat something."

She laid down with her head on a sofa cushion, and put her feet in my lap. I again admired her red toenails through her nylons. I unfastened the ankle strap of her right heel and gently eased her foot out of the sandal. I lifted her foot and kissed her nyloned toes.

She sighed and appeared to enjoy my caress. I took off her other heel and again kissed her stockinged foot and toes, finally resting her feet in my lap stroking them gently. By now I sported an impressive erection tenting my suit pants.

After a while she pulled up her legs and sat up. She slipped back in her sandals and I bent down and fastened her ankle straps again.

She looked into my eyes and we kissed again, our tongues dancing.

I felt her take my hand, placing it on her nyloned thigh where her dress had pulled up to mid-thigh. Then I felt her hand gently rubbing my erection through the suit pants. I sighed and let out a low moan.

"Do you want me to stop? I've never done this before to a man." she whispered.

I groaned: "Don't stop, this is heaven..."

My hand slowly moved up on her thigh, until I reached the welt of her nylon stocking and the garter clip.

"Stockings...??" I asked wide eyed.

She nodded: "I love nylons. I have a real thing for them. Tights are so utilitarian and such passion killers."

"And you look wonderful in your nylons. I've never met anyone wearing them, and they're soo sexy!"

She slowly started to open my belt and unzipped my trousers.

"Are you okay with this?" she asked. I nodded. Couldn't talk. Sighed. Moaned.

I felt her fingers slipping into my boxer shorts, liberating my cock that was oozing precum.

She looked at me with her big brown eyes, my cock now in her hand.

"This is a first for me, I've never done this to anyone..."

She bent down and slowly stated to swirl her tongue around my cockhead licking off the precum. Then I watched her close her lipstick-coated lips close around my cock. Her gaze moved upwards to meet my eyes and she gently started to move her lips up and down my cock, which soon was glistening with saliva and precum. Having been quite excited all evening it didn't take very long for her to take me right to the edge.

"Oooh my god Janine...this feels so good...ooh, please...this is soo hot...oh my god I'm coming...I'm coming...Janine, I'm coming...."

She held my cock in her mouth moving her red lips up and down, looked into my eyes and I watched her swallowing jet after jet of my come.

My breath was rasping, I was moaning and babbling: "Ooh Jesus...that was wonderful...you sexy, beautiful woman..."

Janine cleaned my cock with her tongue, the sat beside me on the sofa and put her lips on mine, our tongues playing and exchanging remnants of my cum.

"I never thought giving head could be so nice, I loved tasting your come, Honey!" she said, smiling at me. "My first time couldn't have been with a nicer person, I really loved it!"

"You can do this anytime you want, Janine! I've never had a blow job as wonderful as this...I nearly fainted, baby, honestly!"

"Ooh, you're a lovely guy, so I reckon you deserved it, Honey..."

I pulled her across and got her to sit on my lap. My hand wandered between her nyloned thighs and moved above the welt of her stockings towards her cock.

"I've taped it, Honey, so I don't tent my dress in case you got me excited. I didn't think I'd get quite so excited, though...please excuse me for a second."

She got up and went to the bathroom, her heels clicking on the hardwood floor.

When she came back, she sat back on my lap and we started making out again, our tongues swirling. My hand continued its exploration between her stockinged thighs, slowly moving upwards.

And there it was, semi-erect, but rapidly getting rock hard as I touched and caressed it. She moaned, and I lifted her off my lap and sat her on the sofa.

I went down on my knees, and kissed a trail up her nyloned thighs until I reached her tenting lace panties. I freed her cock. It looked beautiful. Her cock and her crotch were completely bald, smooth and very beautiful. I had never sucked anyone's cock but nobody in the world could have stopped me from what I was about to do.

Janine was moaning and babbling, and gave a little squeak when I swirled my tongue over her cockhead, wet with precum. I took her rock hard cock in my mouth and started to move my lips up and down.

Clearly, she had been quite excited as well, because after a short few minutes of mewling and softly moaning she rasped quietly: "Oh my god oh my god, Honey...you're sucking my cock...you don't have to do this...it feels wonderful...you're soo sexy...please suck me...oh please...I'm so close...so close...I'm coming...oooh Honey...I'm coming..."

She was sat up, watching me sucking her cock, and, like her before, I looked right into her eyes as she came in my mouth.

To my joy, I wasn't put off at all when she released her come in my mouth. It tasted creamy and a little salty, and swallowing it was pleasant. I kept sucking her cock, cleaning off all the come while stroking up and down her nyloned thighs with both hands.

She collapsed and fell back on the sofa, and when she was clean I came to lay down beside her and we fell into a deep kiss. I continued caressing her stockinged thighs.

Once her breathing had slowed down again she sighed: "My god, that was wonderful, Honey. Thank you so much for accepting me, the way I am. I've never really had a blow job like this...Natalie didn't like oral sex, at least not with men, and before that was just some fumbling. Ooh, Honey, I can't thank you enough.."

I said quietly: "I loved it, Janine. This was my first time as well, and it couldn't have been a more wonderful experience. You've got a beautiful cock, so soft and so hard all at the same time. And I really loved swallowing your cum, it tastes lovely. I can't wait to do it again!"

She looked into my eyes and whispered: "I always loved you as a friend, but after today, I might be falling in love with you. Would you let me do one thing? You said you never felt like the real thing when wearing lingerie and dresses. Let me dress you up. I'll help you with the make-up and hair. I've learned a lot from my mum and who could be any better than a Frenchwoman in all things feminine...?

You're such a gorgeous person, I'd be surprised if I wasn't able to turn you into a beautiful woman. Stay here with me for the weekend, there's enough room and I promise we'll have a lot of fun. It will be soo hot!"

How could I possibly say no?

"Sounds sexy. Sounds fun. I'd love to stay with you. Apart from that, after today, I think I'd let you do anything."

We looked into each others eyes and smiled. Her eyes shone. We kissed. Adventures ahead!

(3)

"Shall I get another drink for us?" I asked.

Janine nodded, I went to the kitchen and opened another bottle of champagne. I returned to the living room and put the bottle in the cooler when she said:

"Take your glass and the cooler." She picked up her flute, took me by the hand and led me to the bedroom. Thoughts about food were forgotten.

Her bedroom was spacious with an enormous super king size bed, walk-in wardrobes and adjacent equally big bathroom with tub and walk-in shower. She told me her dad had bought the loft cheaply and invested some money in converting it. There were no direct neighbours and the apartment had multiplied in value over the years.

She kissed me on my lips and said: "Honey, if you're uncomfortable with anything I do, please say so, and I'll stop. Seriously, I don't want to do things you're not okay with, you're far too important to me."

"I said I'd let you do anything and I mean it, baby. I can't imagine you doing anything to me I don't like."

She asked me in a low voice to take my clothes off. I stepped out of my shoes and peeled my socks off. I gave her my suit, tie and shirt, which she neatly hung up in her wardrobe. I stood there in my boxer shorts and Janine looked at me and sexily licked her lipstick coated red lips

"Well, these will have to come off as well, I'm afraid, for what I have in mind..."

She walked up to me, knelt down on the carpet and pulled my shorts down, kissing my cock as she went along.

Then she got up, hugged me and whispered in my ear: "Have you ever tried anal sex?

I whispered back: " Millie and I tried, but she always was a little impatient, so it never worked out. We finally gave up. But I'd love to explore it..."

She replied: "I couldn't think of anyone else I'd rather explore it with for the first time. I've never done it, but I'm curious. I've often read up on internet sites about it, when I was dressed and felt feminine. The consensus seems to be that it's bad when it's rough, but if you're patient and gentle there's nothing quite like it. Honey, would you like to be my first? I trust you, and I'd love you to take my anal virginity. And I'd love to do it when we're both dressed up!"

This came all a bit fast, but, needless to say, I was extremely turned on. I'd known this person for a long time and I trusted her, man or woman.

"As long as you stop me, if I hurt you. I would never want to hurt you, baby. And, of course, only if you promise to reciprocate. Getting anally deflowered by the most beautiful woman I've ever seen while dressed up sounds incredibly hot..."

She looked at me with her big brown eyes, gave me a big smile, and said: "It's a deal, then!. Ooh Honey, I cant wait. I get so hot, just talking to you."

We kissed deeply, our tongues swirling. I felt my cock stirring again.

Janine asked me to unzip the back of her dress and untied the bow of her wide belt. Her dress pooled around her and she stepped out of it, picked it up and hung it in her wardrobe.

She stood before me in black lacy bra and knickers, black suspender belt, cinnamon-coloured nylons and heels, looking unbelievably beautiful. I told her and she looked at me and wrapped her arms around me and kissed me again, her tongue exploring. The touch of her nylons on my bare skin made my cock stir. My head was spinning.

She sat down on a stool, slipped off her heels, carefully unclipped her nylons and slowly took them off, all the while looking straight at me.

I went behind her, knelt, and unclasped her bra, kissing her back and shoulders, eliciting a long sigh from her. I reached around her and gently stroked her nipples and her sigh became a low moan. She stood up and I slowly pulled her knickers down, continuing to kiss her shoulders, back and tight ass cheeks.

We were both naked. Her body was entirely hairless and she looked wonderful.

Then I reached around her. I felt her cock becoming semi-rigid and she quietly said, with a hoarse voice: "Let's continue this in the shower."