Waking up with Marsha

While laying in bed that morning, Marsha was spooning my naked body from behind. She was idly playing with my small, thin penis while kissing the back of my neck and shoulder. I had just woken up and was squirming back against her in response to her touch.

Her voice was raspy, "I am still amazed you did that last night."

I giggled while wiggling my bottom against her hips. "Did you have fun?"

She chuckled, "Yes. I definitely had fun." After kissing my neck, just beneath my ear, she whispered, "I've been with lots of boys. But you are the first to ever take that strap on."

Squirming back against her, "It was awfully big. I'm surprised I was able to do that too!"

Marsha began slowly humping her hips against my narrow, bare bottom. "Looks like I'm going to have to shop for an even bigger one for my new favorite boy!"

Turning my head so I could better see her. Marsha was nearly 20 years my senior. She had picked me up at the coffee shop I work at after flirting with me shamelessly for weeks! She was what one would expect a 40-ish woman to look like. The roots of her long, light brown hair were beginning to gray. She had wrinkles in all the usual places. She was busty but dressed in a way to detract attention from them. The nipples on her breasts were as big around as pancakes and the nub stood out proudly from my breast. She had wide hips that turned out to be quite powerful, I learned that the night before. She was tall, standing several inches above my five feet, four inches. She wasn't necessarily full-figured, but she wasn't thin either. She had big, blue eyes and a wonderful smile. Marsha was a very attractive woman and I felt honored to have her interested in me.

While my heart filled with joy, I excitedly asked, "Am I really your favorite boy?"

She kissed my earlobe, "Sweetheart if you keep surprising me like you did last night, I may never let you leave my house. Yes, you are my favorite boy!"

My mind began to race while thinking of different ways I might surprise her. She'd already taken me with her largest strap-on. Doing that again would hardly surprise her. My mind was blank. I had no idea how to keep surprising her. In a soft voice, I asked, "Any suggestions on how I could surprise you?"

My little penis had responded to all her teasing and become completely erect. It was its full size, almost 4-inches, but still terribly thin. The night before, Marsha had compared the size of her vibrator to my penis. While her vibrator was a foot long and as big around as my wrist, my penis was looked like a thumbtack while standing beside it. Thankfully Marsha hadn't picked me up for a traditional relationship or traditional sex. She enjoyed being pleased orally and using her strap-ons. While I preferred manual stimulation and anal penetration.

She nipped my earlobe with her teeth before whispering, "It wouldn't be a surprise if I told you what to do, would it?"

Biting my lip, I wiggled my hips back against her and giggled, "I guess not."

She nipped my earlobe again, "Just be yourself. Do the things you've always wanted to do, but were afraid to with anyone else."

While lying there with Marsha still gently teasing my little prong, my inhibitions began to slip away as I confessed a few things I'd thought about before, "Like shaving away all my body hair?"

She nipped my earlobe hard enough to make me jump. She then almost growled in my ear, "Fuck yes! Just like that!"

I squirmed back against her while whispering, "And what if I met you wearing..." I was about to utter a part of my deepest secret, I had to pause to summon all my courage. "...panties?"

She paused and her tone became very serious sounding when she said, "Well, if you answered the door of your little apartment wearing nothing more than panties to meet me for an evening together..." She let the thought linger in the air for several seconds before moaning, "I'd drive you straight here, strip you out of those panties before I fucked you until you were unable to speak in complete sentences. And you sure as hell wouldn't be able to work the next day."

She rose up and leaned over me, stared into my eyes for a moment before leaning down and kissing me with enough passion to make my toes curl. As our lips separated, she whispered, "Baby Boy, I'd love it if you wore panties. Now don't tell me any more ideas. Surprise me! You seem to know the sorts of things I'd love to see you do, so just do them for me. Okay?"

I whimpered softly, "Okay." While snuggling back against her grinding hips.

We continued to lay in bed together for several more hours. Marsha teased my little penis until it squirted, twice. I spent time under the covers, between her thighs feasting on her big, meaty pussy. By the time I'd finished, I lost count of the number of times she came. Her clit was swollen, bright pink, and glistening with my saliva by the time I crawled out from between her legs.

By the time we got out of bed, it was late morning. We showered together and ate a light brunch before Marsha drove me home and walked me to my apartment door. When I asked if she wanted to come inside, she politely declined but told me she'd be by to pick me up that same evening at 7 pm to take me out to dinner. She then winked at me before kissing me on the lips and leaving.

Thankfully, I'd arranged to have my shift covered that day or I would have had to go work less than an hour after being dropped off. The next several hours went by in a blur. If Marsha wanted to be surprised, I would do my very best to surprise her!

While in the tub, shaving away what little hair I had below my nose, I finalized my plan. After I'd finished shaving, I drained the tub and rinsed off in the shower before washing myself twice. Once I'd dried myself, I double-checked to be sure I hadn't missed any stubble or wisps of hair. Dusting myself with powder was the next step, I used my powder with the floral scent. I'd bought it months before and had never even tried it out.

Bending down, I picked out my cotton-candy pink nail polish from my small collection. I also grabbed my toe-separators. Moving across the room, I sat on the seat of the toilet and polished both my finger and toenails. I sat there rather impatiently while blowing on my fingers and toes trying to will them to dry faster. After returning the polish and foam toe-separators to their place under my sink, I checked my nails one last time.

Moving to my little bedroom, I opened my closet and moved all my regular clothes aside to separate them from my girl's things. Having already decided what I'd wear, I plucked the white summer dress from my wardrobe, grabbed my white sandals with the kitten heel, and hung the dress from the hook on the bedroom door setting the sandals down beneath it. Moving away from the closet, I went to my dresser, from the bottom drawer, I moved the t-shirts kept down there to conceal my small collection of toys. I immediately zeroed in on my little pink chastity cage. I had to dig around a little before I found the small silver lock and its key. I paused to run back to the bathroom and dust my penis with even more powder.

On my way back to my bedroom, my phone rang. I had to run around to find it. When I did finally locate it, I saw it was from my work. It turned out to be the girl covering my shift. She told me she was trying to make some extra money for her boyfriend's birthday later that same week. She asked if I would like her to cover my shift the next day as well. Thoughts of the evening I had ahead of myself began to fill my mind, but I refocused my attention on the call and told her that would be fine. We chatted a little more about work before saying our goodbyes.

By the time I'd hung up the phone my penis was wilted to its usual size. Right there in the living room, I put myself into the chastity cage. Racing back to my bedroom, I slipped the lock in and clicked it shut. Returning to the living room, I set the key down on the table beside my front door. Scampering back to my bedroom, I found myself giggling like crazy while I stepped into my dress and pulled it up into place. Turning to face the mirror, I closed the 4 or 5 buttons down the front of my above-the-knee length dress. When I'd finished, I struck several poses for my own reflection. I thought I looked really cute in that dress! And the chastity cage minimized any unsightly bumps that might arise.

Checking the time, I was going to be ready hours before Marsha was due to arrive. Nibbling on my lower lip, I decided to call her. While standing there, staring at my reflection, I listened to her phone ring twice before she picked up.

She answered the phone in her car with a chuckle, "It looks like you're just as excited to see me, as I am to see you!"

Biting my lower lip, I squeaked, "I am! I really am!" I paused before blurting out, "Do we have to wait until later tonight? I'm going to be ready in 20 minutes..."

Marsha cut me off before I could finish what I was going to say, "Perfect! I can be there in 20 minutes."

I moaned softly into the phone, "Thank goodness!"

She had a spark in her tone when she ended the call with, "See you in twenty."

I dashed to the bathroom to finish getting ready. After brushing my teeth and mouth, I swished around my mouthwash to ensure my breath was fresh. Looking at my reflection, my hair had dried more than I wanted. I wet my brush and ran it through my hair to moisten it before adding a bit of gel. I usually wore my hair mostly flat against my head. But when I dressed up, I liked to poof it up a bit. Standing at my mirror, I played with my hair until I was satisfied with the result. I didn't necessarily look like a girl, but I looked less like a boy than I usually did. The last thing I did before leaving the bathroom was applying a thick coating of pink-tinted lip-gloss with a little added glitter.

Returning to my bedroom, I sat on my bed and buckled my strappy sandals on. The heel was less than 2-inches and easy for me to walk in. Anything more, and I looked awkward while moving around. I paused to admire my toenails for a brief moment, I really liked that polish!

I'd just stepped in front of my mirror to have one last look at my reflection when I heard a firm knock on my door. My little penis immediately swelled as much as it could and filled the small space the cage allowed. I felt my heart begin to race as I stepped toward the door. Marsha would be the first person to ever see me dressed up. I'd never shared a picture online, nor had I ever been caught! I felt mildly ill as I peeked out the peephole. Marsha was standing there waiting for me to answer.

Stepping back, I fluffed my dress before reaching for the knob. Taking a deep breath, I said a quick, silent prayer that Marsha would respond positively to my appearance. In one movement, I threw the door open all the way and shared my deepest, darkest secrets with someone for the very first time.

Marsha's eyes and mouth opened wide. She didn't move for a second or two and I began to consider moving to another town. But then her mouth closed and was replaced by a grin. "Oh my! You do not disappoint! I was expecting panties. But this, THIS is so much better."

I finally began to calm down and my stomach settled. Marsha stepped into my apartment and I stepped back as she did. Even while she closed the door, she kept her eyes locked on me. I found myself posing for her!

After we'd both calmed down, I giggled, "I'm really glad you like me like this. You're the first person who has seen me dressed."

Marsha stepped close and took me in her arms. I reached up and looped my skinny arms around her neck when she leaned down and kissed me passionately. When the kiss came to an end, she whispered, "Sweetheart, I'm glad you chose me to be the first to see you. But I can't be the only one. You're far too cute to keep hidden behind closed doors. Come on, let's go get a late lunch. I know the perfect place."

I stepped back. "No! No way! I can't go to a restaurant like this!"

Her tone and expression became very serious, "Young lady, are you sassing me? Do you know what happens to backtalking girls?"

I bit my lower lip, my penis continued to fill this small space it was allowed, my hips wiggled a little while slowly shaking my head. Even while being scolded, I felt a warm feeling blossom in my chest at her referring to me as 'young lady'. I took it as a sign that she thought of me as a girl while I was dressed.

She stepped closer, her voice remaining very firm, "Sassy young ladies get their mouths washed out with soap and spend time in the corner. Is that what you need?"

I stood there silently, shocked at what she said and a bit frightened by her change in tone and promise of punishment.

Her tone softened and her stance relaxed when she next spoke. "I didn't think so. Now grab the key to your apartment and we'll go out to a nice lunch together."

When I picked up my keys from the table beside the door, I opened my mouth to tell her about the chastity cage I was wearing. Before I could get a word out, she cut me off, "Not a word! Give me your keys." After I'd handed them to her, she asked, "Which one is the key to this door?", she pointed to my front door.

Biting my lower lip, I tasted my lip-gloss while pointing out the correct key. While she pulled it off the ring which contained other keys to my car, my post office box, and the small storage area the landlord provided. I glanced down at the keys to my chastity cage laying there helplessly on the table and a thought crossed my mind. I'd worn my cage while playing with my dildo before. But I'd never worn it while with someone else and definitely not overnight. It might be fun? But on the other hand, it might prove to be excruciating. Marsha wasn't giving me a choice. It looks like I'd have to endure the night I had ahead of myself with my little penis safely locked away in its cage.

Marsha took my hand and led me out to the sidewalk in front of my apartment. I stood by while she locked my door before dropping my key into her purse. Taking my hand again, she led me to her car and opened the door for me. Marsha closed my door, but not before reminding me to buckle up. She then walked around the car and climbed behind the wheel. When she sat down, the entire car tilted toward the driver's side. I bit my lip and felt my penis attempt to stiffen more than it already was. We'd left my apartment and walked to her car without saying more than a few words.

After she'd started the car, I almost spoke up and told her about what else I was wearing. But I decided to remain silent until I was sure she was no longer upset with my behavior. I sat there, perched on the passenger's seat with my hands folded in my lap. Out of the corner of my eye, I saw Marsha look at me several times while she drove.

After a few blocks, she said, "I like your nail polish, Sweetheart. It's the perfect color for you."

I giggled, "Thank you."

While at a stop sign, she reached over and slid her fingers over my freshly shaven thigh. In a teasing tone, she asked, "Did you shave everywhere for me?"

I squirmed in my seat, "You'll have to wait to find out!"

Marsha replied with a cheerful tone in her voice, "Or you could show me right now!"

I briefly thought about lifting my dress and showing her my caged penis. But instead, I giggled, "It's a surprise!"

She returned her attention to the road before saying, "I did say I liked to be surprised. And you, young lady, have proven to be full of them!"

I timidly asked, "They're good surprises so far? You like them so far?"

Reaching over, she set her hand down on my bare thigh and left it there. "I love your surprises. Remember what I said about keeping you at my house forever? You're well on your way to changing your permanent address."

I squirmed and wiggled in my seat. Not only did she accept me as a young lady while I was dressed, but she was also still considering having me move in with her! Yes, we'd only spent one night together, but it was clear that we fit. There was an age difference, but I looked at that as a positive. Marsha was proving to be the matronly figure that had always been missing from my life. She had a temper and made a promise of punishment, which sort of turned me on in a strange way.

As she drove, we chatted about our previous evening together and she told me what she accomplished while I was getting ready. She'd run several errands and had the oil changed in her car. After she'd shared that with me, she teasingly asked, "I'm assuming you don't know how to change the oil in a car, do you, princess?"

Giggling and squirming, I squeaked, "No!"

While watching the road, she said, "I didn't think you would. That's not something proper young ladies are taught."

I didn't answer, I didn't need to. Marsha turned onto the old shopping area, the main street that had been redone to make it more desirable to visit. I couldn't afford to shop in any of those stores, but I liked to drive down there around the holidays to see the lights.

Marsha pulled to a stop in a space directly in front of a quaint little breakfast and lunch restaurant called, 'Dreamtime Café'. After climbing out of the car, she came around to my side and helped me out. She closed the door behind me and paused. In a quiet tone, she asked, "How do you feel about speaking to strangers? Or would you like me to do all the talking?"

I shivered with fear, I was about to walk into a restaurant dressed! My little penis should have retreated into my body in fear. But no, it was filling its cage and struggling to keep swelling. I squirmed in discomfort while whimpering, "Please talk for me." She almost turned away to lead me to the restaurant, but I pulled back on her hand. When she looked back at me, I'm sure she saw the fear in my eyes. I whimpered, "Do we have to do this, Marsha? I'm really scared!"

She smiled warmly before taking me in her arms and embracing me right there on the street. In a soft voice she told me, "Yes, we are going to do this. And I'll do all the talking for you. You don't need to worry. Sweetheart, no one is going to guess you're anything except a nicely dressed young lady. Trust me."

While still scared, I nodded my head because I did trust her. Yes, I hadn't known her for long. But she was the sort of person I found trustworthy. Marsha stepped back from our embrace but kept hold of one of my hands. Together, we walked toward the restaurant. My heart was pounding in my chest and I found myself looking at my feet.

Marsha whispered, "Young ladies stand up straight."

I giggled while straightening up. I clung to her hand while she opened the door and I stepped inside to be facing a girl my age behind a small podium. In a perky voice, she asked, "Welcome to the Dreamtime Café! How many in your party this morning?"

Marsha stepped forward and spoke up, "Just two. It'll just be my niece and me today."

The girl scribbled something down on her tablet before returning her attention to us. "Please follow me!"

Marsha and I wound up being seated in an enormous booth big enough for six or eight people. We both scooted together on the far side of the big table. Water and menus were soon dropped off by an equally perky waitress. When asked about our drink order, Marsha said, "I'll have coffee and my niece will have a small apple juice."

As soon as the waitress stepped away, Marsha leaned in close and whispered in my ear, "You'll be having a light lunch. I don't want you to be filled up when I'm fucking the hell out of you as soon as we get home."

My silly penis swelled up and cramped itself in the cage. I whimpered softly. "I need to tell you something." I was about to share with her the additional secret I was wearing under my dress when I saw the waitress returning with our drinks.