Saturday Morning

This is the second in a series, the first being my story An Unexpected Friday.

Daylight shown through the drawn curtains that hung over the sliding glass door, touching the end of the bed. As I lay there the experience of the previous night came back, and the erection that I woke with pulsed against the hotel sheets. Closing my eyes again I touched myself and went over the details in my mind....meeting Diana at the hotel bar, her invitation to come up for a drink, and the amazing time that followed. Rolling over, I pressed my body down onto the mattress, feeling the hardness of my cock as I thought about Diana's and recalling the end of the night...

I lay on the bed, spent, gazing up at this person I had just met, with whom I had shared my deepest secret, feeling suddenly vulnerable. Diana gazed at me for a long moment, our eyes meeting as she slowly trailed her hand up my chest, cupping my cheek. Cross legged next to me she bent over, lightly trailing her lips over mine, and then moved off the bed and towards the room's bathroom. I turned my head to watch her walk away. After a few minutes passed, I closed my eyes, feeling exhausted and spent. It had been a long day...

I drifted off a bit, and then awoke to a warm washcloth gently cleaning my crotch. Opening my eyes I saw Diana. She now wore a loose fitting pair of silk pajamas in a deep blue. I could see a glimpse of the black bra she still wore, cradling her heavy forms. She had fixed her makeup a bit, and her grey hair once again framed the soft skin of her face. I felt my cock stir under her touch as she cleaned me of her cum and mine.

Seeing me awake, she smiled. "Time to go" she said.

I was hurt, I admit. Searching for something to say, I questioned her with my eyes.

"That was....wonderful..." she said, smiling, "and I look forward to more times

like it. But it's late, and you have had a full day and then some. And a flight tomorrow." She gently took my cock in her hand, her painted nails showing as she used it to steer me to the bed's edge. As I sat up she kissed its tip lightly, then looked me in the eye as she picked up my underpants and began to ease them up my legs. As I sat on the edge she then helped me into my pants, and then gestured me to hold my arms out and placed my dress shirt on me.

"I like to help my man get dressed" she said, slowly buttoning the shirt. I could see the movement of her cock beneath the soft silk of her pajamas. Her hands caressed my now covered chest. "It's part of the thrill at the end of the night, a final scene in our illusion." She smiled.

I brought my hand up, brushing it over her crotch, feeling her erection beneath the silk.

"Oh yes" she murmured, moving her hand over me as well. "Oh yes."

I relaxed, comfortable again. I bent down to put my socks and shoes on, and then stood, pushing my tie into my pocket. Looking down at her I raised my hand and brushed the soft skin of her cheek, silent. I followed her to the door. Facing her, I bent my head, brushed her lips with mine, taking from her a last taste of her lipstick.

"You spoke of room service for breakfast. Can I persuade you to let me buy you brunch instead?" I asked.

"Oh yes." she whispered. "Sweet dreams."

And with that I was out in the hallway, the faint smell of her perfume clinging to me.

I rolled over in the bed. A glance at the clock showed me that I had some time before I had to get dressed and meet Diana in the lobby. My cock rested against my belly, throbbing with desire. Closing my eyes I remembered the feeling of Diana in my mouth, moving in and out, the soft skin of her ass under my caressing fingers. I slowly reached down, stroking myself, remembering her soft hands and painted nails as she had touched me, remembering the gentle pressure of her finger as she penetrated me. I lifted my knees, reaching down with my left hand and feeling the soft skin around my asshole, still a bit slippery and soft from the lube she had put there. Her scent still clung faintly on me. The way I had moved my tongue on her small shaft, the sight of her trimmed landing strip as she stood before me. Still stroking with my right I pushed on my hole with my left index finger. The slightest of pressure there and I arched up, exploding all over myself, shooting cum up my chest, remembering the feel of her.

I lay quiescent a moment, feeling my heart rate drop back down, breathing quietly.

Getting out of bed I turned on the room coffee maker, and jumped in the shower. I didn't want to lose the smell of her on me, but I was sure that Diana wanted a clean man to have brunch with. I washed and shaved, and then dressed in what I had brought, casual jeans, and a dress shirt. Comfortable traveling clothes; I hadn't planned on meeting and having breakfast with a beautiful and elegant mature lady, but they would have to do. Quickly packing my overnight bag, with one last glance around the room I left a tip on the bedside table and headed down to the lobby.

After checking out and arranging for my luggage to be held while we had brunch, I took a seat in the lobby, glancing at my watch as I did so. Enough time for a leisurely brunch, and then I'd catch the shuttle to the airport and my flight home. Just as I looked up from my watch the elevator doors opened, and my heart skipped a beat as Diana walked from the elevator. She glanced around the lobby and spotted me. As she strode across the lobby towards me she smiled.

"Good morning Marc," she said softly as I rose to meet her. Her hand reached up and brushed the collar of my shirt. "Don't you look handsome in the morning light." Her eyes met mine, shining with pleasure.

.

Diana was wearing a simple sweater dress this morning, of a dusty rose color, under a black oversized leather jacket. The wool of the crew necked dress curved from the soft skin of her neck over her generous chest, and dropped to just below her knees, hugging her hips before flaring out a bit at the hemline. Her legs were in black hose, and the outfit was completed by black calf height boots, with a small heel. A silver necklace hung on her chest, with a small locket that nestled in the valley of her breasts. A large black leather purse completed the ensemble.

She had accentuated her eyes with a light eyeshadow, and her lips were a tone of rose pink that reflected her dress. I drew my breath at her simple and yet overwhelmingly sexy look. Her eyes held mine, with just a hint of a question in them. I leaned in, and brushed her cheek with my lips, catching, as I did so, another hint of her perfume. "You look wonderful" I whispered. "Just the thing for breakfast." I felt my cock stirring in my pants.

"Well thank you dear, but perhaps we should eat first," she smiled mischievously, hooking her arm through mine as we walked into the hotel restaurant.

As we stood at the table she removed her jacket, draping it over the back of her chair. Her dress showed itself to be sleeveless. The knit fabric curved over her boobs, accentuating their fullness as it swept back under her arms. The soft skin of her upper arms showed that she kept herself in good shape.

"So, Marc," she said as we settled in, and the waitress poured coffee."I admit to some nervousness. I've been stood up for breakfast too many times to mention. My heart fluttered a bit when I spotted you, I must say. Too many men wake in the morning and consider the events of the previous night as over and done with."

"Well they are fools then," I said looking into her eyes, reaching across the table to take her hand. "You look as beautiful in the morning light as you did last night sitting at the bar." She shifted slightly in her seat, smiling as she lifted her menu.

We ordered breakfast, and then discussed her plans for the day. She planned to do some clothes shopping at several of the large department stores in the city, and then return to the hotel. A workout in the hotel gym, and then a quiet evening. "It takes some effort to maintain this figure," she smiled. "And no bar tonight...I found what I needed last evening." She toyed with my fingers as she said this.

"And you, Marc...had I been a bit more perceptive last night, I would have noticed or guessed your secret as well. Your hands are so soft..." she trailed off. She was inviting me to tell her my story.

I felt a flush. I had told her my secret, that I crossdressed, last night in our moment of passion, but I was far more in the closet than she. "You weren't taking advantage of a night away to dress?" She questioned, tilting her head.

Hesitantly I explained that I hadn't felt that I had the time on this trip- it was a simple overnight business trip, and that I usually needed more time to relax and indulge in my hobby. And more importantly that it was something I had only indulged in in the privacy of my apartment.

"That being said" I smiled "I did pack at least a few things, and I'm wearing one of them now." My stomach leapt at bit at my boldness- but I felt so comfortable with her. Our fingers continued to softly caress each other as we spoke. My cock came fully erect in the satin full cut panties I was wearing under my jeans as she raised an eyebrow at me.

"Really...." she grinned. "Will I be lucky enough to see this before you fly out?"

"I guess that depends on how long breakfast takes," I murmured, as I looked deeply into her eyes and took up my knife and fork. I was flushing again. I wasn't really used to discussing my cross dressing, which, while it was something I had done for as long as I could remember, remained a secret. But Diana was a good ten years older than me, and with her years of experience, and with her comfort at being open, began to draw me out, gently asking questions.

I explained to her that I had memories of dressing with my sister when I was young, of feeling even then a thrill I didn't at the time understand. And then adolescence, when my father had remarried, and I would sneak into my step mothers drawers to try on her clothes. My first orgasm, as a rubbed my sisters satin nightdress over my penis. Years of high school and college, in which the general overwhelming flood of hormones had suppressed, for a time, my urges. The questioning of myself: Where did this need come from? I had wondered all my life. What was that secret warm feeling I would get when dressed in an item of the opposite gender's clothing? What created not only this sexual thrill, but that deep sense of comfort? Of course I had researched it, had determined that I was "straight" and that what I was doing, even as I felt shame, was acceptable in many cultures throughout history....

All of this came out as I spoke with her, along with a short history of my successful relationships with women, until reaching my late 30's. Of the feelings re-emerging in my last relationship, of trying on my girlfriend's outfits while she was away. And then, as I began to explore the internet, I had found kindred souls, but these were men who embraced their femininity, that posted photos of themselves online for admirers to see. I no longer felt so alone- others did indeed share my feelings, the thrill of wearing the clothes of the other. And exploring this world, I began to acknowledge to myself (how could I not? My reactions were obvious) that looking at these pictures turned me on, excited me sexually. And the older I got, the more comfortable I was with these feelings....

"Marc..." Diana interjected in her soft voice, her blue eyes gazing into mine as I revealed to her my deepest secrets.

"But you were my first." I stated, and felt my heart move as I exposed my vulnerability. I was felt wide open and exposed.

"Oh Marc" Diana sighed, moving again in her chair, bending forward to stoke my cheek. We gazed at each other for a long moment. Suddenly she sat back. Catching the waitresses attention she called for the check. "I've suddenly realized I've forgotten something in my room," she said lightheartedly, breaking the tension. "Shall we go up and get it, before you catch the airport shuttle?" Butterflies suddenly started in my stomach as she rose, pulling her jacket off the back of the chair and folding it over her arm to hold it in front of her. A flush now rose under the light powder of her cheeks. We left, and strode towards the elevator.

Arriving at the room she tossed her jacket at the bed and turned quickly to me.

"My God Marc. You almost showed me up down there. I shouldn't have chosen today to go, as the kids say, 'commando' " she glanced down, chucking. Looking down I could see the soft wool of her dress bulging as her small cock pushed it up and out. "Your speech down there really got me going. I never expected that open truth. I hadn't expected to get that excited at my age. But I didn't want to show panty lines in this dress. " she laughed, pushing her palms down her side to smooth the knit fabric over her hips. "Jesus" she murmured. Her eyes were full of lust as I met them.

I brushed her cheek with my lips, careful not to disturb her makeup before a day out. "Let me take care of that for you" I whispered in her ear, my own cock straining in my panties as I eased the stretchy wool up over her hips and pushed her back into a chair. She wore a simple black garter belt, her black stockings rising to mid thigh and held in place with silky straps. As she had told me, she wore no panties, and her beautiful cock had risen to attention.

I quickly bent and once again took her small cock into my mouth. Closing my eyes, I brought my face down until my nose touched her small landing strip, and then inhaled her scent. I could hear her sigh above me, as I slowly withdrew, lingering on the tip for a moment and then kissing and licking it, feeling its shape with my tongue. Bringing my eyes up I saw her face, tilted back, eyes closed, framed by her heavy breasts under the knit of her dress. Her hands moved to cradle my head. I began to suck her, slowly at first and then increasing my pace. Her breathing quickened, and she began to thrust gently, in time with my movements. I could feel my own cock straining against the smooth fabric of my panties. Up and down my head went, as my left hand toyed with one of her garter straps and I brought my right in to cup her balls, moving my fingers to encircle them. Diana began thrusting harder as her moment approached, and quietly began to moan.

"Marc..." she said. "I'm going to cum," warning me. Looking up, I met her eyes as she looked down at me. I continued to suck, moving in time with her rythm. I was struggling to control the orgasm I could feel coming on within me as I witnessed her pleasure. Her chest heaved under the wool of her dress. "Oh Marc...." she gasped as with one last thrust she exploded in my mouth. Struggling not to gag I felt her warm cum flood into my mouth. It was the first time I had tasted another's. As I felt it spread in my mouth my own cock let go in my panties, squirting beyond my control, and I felt the wetness spread in my crotch.

Her cock softening in my mouth, I lingered as I withdrew my head, reluctant to let go but knowing we were short on time. Diana leaned back in the chair, her eyes closed as she relaxed, her breath slowing. I rose, and walking to the bathroom, came back with a few hand towels, and slowly cleaned her cock and balls of my saliva and her cum. I pulled her up out of the chair, and kneeling down again I smoothed the dress down over her thighs, running my hands all the way down her legs, cupping her calves, enjoying the sensual feel of the textures of her soft wool dress and silky stockings.

Standing in front of me, Diana half closed her eyes and whispered "Mmmm. That takes care of me...but how about you?" She placed her hand at the back of my waist, running her fingers under my waistband. Her eyes widened and she smiled as she felt the lace elastic

of the top of my panties. "What have we here? " she grinned mischievously.

I flushed, and whispered as her hand moved around to the front of my pants. "Well actually...." I trailed off.

Pushing down into my pants to touch me she felt the wet of my own cum, brushed her fingers over my now soft cock. "Marc, " she asked, looking at me with her cocked eyebrow. "Did sucking me off do that to you? My God just that thought may get me hard again." She laughed. Withdrawing her hand she put her fingers to her mouth, tasting me.

"But we are out of time. Get out of those pants" she commanded, turning away to her suitcase.

"Why? Oh..." I said as I saw her turn back holding in her hands a some pink panties. I quickly got underdressed, and taking the towels I had cleaned her with, she cleaned me up. I stood as she knelt and drew her panties up over my legs, feeling them cup my cock and balls as she settled them around my hips. Moving her hands to the front could feel my cock stir under her massaging fingers, and chuckled. "Your getting hard again. But there's no time left my dear," she laughed. "You'll have to deal with that yourself when you get home." The thought of wearing her panties had made me fully erect again. I couldn't believe how turned on her presence made me.

With a last long caress she stepped back, and I put my pants on. I saw her watch as I struggled to make my erection comfortable. The feeling of wearing Diana's panties was incredible.

"I want you to know that I have the biggest crush on you right now" I said, glancing shyly up.

"If wearing my underwear does that to you that fast, I can see we have quite the future ahead of us. " Diana said, her blue eyes now soft. "I'll get these back to you," she said playfully, holding my panties in her hand.

I moved towards her and brushing her grey hair back I kissed her lightly and longly, careful not to disturb her makeup but wanting a taste of her pink lipstick. Her soft skin drove me wild, and I smelled again her floral perfume. Her arms encircled me and her heavy breasts pushed onto my chest. "Thank you for a wonderful start to my weekend." She said. "This heart of mine is old enough to know how to protect itself, but there's a corner of it that's yours." She pushed me away. "Now go. And travel safely."

"Thank you, Diana" I whispered, lingering to look at her in her dress. "I'll see you soon, I hope."

"Oh yes...I'm sure you will" her eyes held mine, and I turned away and closed the door behind me.