One evening, I had agreed to join a large group of friends for dinner at a local restaurant. One of my friends brought along a woman named, Ruby. I sat next to her that night and knew at first glance, we were physically complete opposites. She was a decade older than me, very tall with long, straight dark hair pulled back in a huge ponytail. She was extremely fit and obviously visited a gym on a very regular basis. She had muscle definition that I would never be able to achieve no matter how hard I tried. I, on the other hand, had curly strawberry blonde hair, a very fair complexion, stood a mere 5’3″ tall and was skinny as a rail with zero muscle definition. When we shook hands after being introduced, my small hand disappeared into her massive, strong hand. She was like a giant in every way when compared to me.

We spent much of that evening getting to know each other. It became apparent that we had many of the same interests. We both loved movies, especially romantic comedies. We both appreciated a good meal. And neither of us had ever had good experiences with relationships. Ruby, because she was taller, stronger and more confident than most men. And I, because I was shorter, unusually cute for a boy and not inclined to make decisions on my own.

We exchanged phone numbers that evening and over the next few weeks, we called and texted each other at least every other day. One particular morning, she called me just as I stepped out of the shower. When I told her I was dripping wet, she chuckled and asked me to send her a selfie. With her still on the line, I held my phone out and took a quick pic of my smiling face. My usually curly hair was matted down against my head and water droplets covered my face. I attached it to a text and sent it to her. After looking at the pic, she told me she hoped I’d show her more.

Her words stunned me. I’d always had a secret exhibitionist streak. The idea of showing my naked body to anyone was my premier fantasy. But I never thought I was the sort of guy any girl or woman would want to see naked. And I’d never had the courage to let someone see my naked body. But the opportunity to do just that had arisen.

I giggled into the phone, “One sec!”

Dropping my towel, I turned to face the full-length mirror on the back of my bathroom door and struck a pose. My pale, body was wet and glistened in the light. My little, pink penis with its dusting of light blonde pubic hair was far from masculine. No, it was cute. That’s the only word that would ever properly describe it. I wound up taking four pictures before I was satisfied with the result. By that time, my penis was fully erect and stood proud at just over 3-inches.

I didn’t say anything on the phone. I just texted the picture to her and waited for her response.

When Ruby spoke, she was unmistakably excited and thrilled, “Oh my God! Casey, you’re adorable!”

I stood there naked, looking at myself in the mirror, “Stop it.”

Her voice was a bit deeper than usual when she said, “I’m not kidding. You are the cutest boy I’ve ever seen!”

I giggled, “Boy?”

She paused, I guessed to look at my picture again, “Let’s be honest, you don’t look like a man. You’re too cute.” Another pause, “Send me another one of your butt.”

I squirmed when she asked for a second picture. It was like a dream come true. I was showing my naked body to Ruby! Turning around, I looked over my shoulder and snapped off several pictures. After sorting through them, I chose my favorite and sent it to her. Without saying a word, I took a few close-up pictures of my very erect penis. My hand was shaking when I pushed the send button with that picture attached.

The phone sat by my ear for several long moments before I heard Ruby’s heavy breathing. She spoke in that same deep tone, “Casey, what are you doing today?”

I watched myself bite my lower lip in the mirror before saying, “Hopefully spending the day with you.”

“I’ll be by to pick you up in 20 minutes. And Casey, wear something cute for me.”

Those twenty minutes went by in a blur. I finished getting ready in the bathroom and then struggled to find an outfit that was ‘cute’. I tried on a dozen different things, but couldn’t make a decision. I was standing in front of my closet, naked and my penis was still mostly stiff when I heard the knock on my door. I wasn’t expecting anyone else, it had to be Ruby.

I’d always wanted to show my naked body to someone. That morning I’d sent pictures of it to Ruby. But now she was just outside. I nibbled on my lip as I tip-toed to my door and looked out the peephole. Ruby stood in the hallway just outside my apartment door. I summoned all my courage and turned the lock on the deadbolt. Reaching down, I slowly turned the knob and opened my door while hiding behind it.

I poked my head around the door and with her still standing in the hallway, I bit my lip and said, “I couldn’t decide what to wear!” And then I stepped out from behind the door and exposed my 5’3″, skinny, pale body with my thin, little, pink erection to Ruby.

She hesitated for only a split second before stepping into my apartment and closing the door behind her. Ruby looked even taller and stronger than usual while standing in my apartment. She had to be close to six feet tall! Even through the white t-shirt she wore, I could see the outline of the muscles across her shoulders, abdomen, and biceps. Her breasts seemed enormous, but I was sure they were mostly muscle. She wore black, spandex-y pants that emphasized her muscular thighs and rock-solid shins. She was a giant!

I backed into the middle of the room while still facing her. Ruby stopped approaching me when she stood several feet away. Her eyes wandered up and down my naked, pale body. Her chest was rising and falling with her heavy breathing. Even while standing there casually, she looked like she was posing for a bodybuilder competition.

She spoke with that familiar deep tone, “You don’t need to wear anything. I think you look perfect just the way you are.” And she took several slow, measured steps toward me.

I giggled and laced my hands behind my back to keep from covering myself with them. Looking up into her eyes, I asked, “Do you really think so? You’re not teasing me, are you Ruby?”

She gently took hold of my arms and looked down into my eyes while saying, “Casey, I’ve never seen anyone that is even close to being as cute as you are. You are perfectly adorable. And I think it’s sexy that you’re not covering up at all.”

I blushed and giggled while standing there glancing between her face and her chest. My voice sounded squeaky when I uttered, “I sort of always wanted to do this. You know, be naked in front of someone.”

Taking my hand in hers, she guided me to my couch. After taking a seat, she pulled me down so I sat across her lap. She wrapped one of her big strong arms around my back and rested her other hand on my naked thigh, halfway between my knee and my groin.

“Am I the first girl you’ve ever sent naked pictures to?”

Nodding my head up and down slowly, I whispered, “Yes.”

Her voice was a bit raspy when she asked, “And I’m the first girl you’ve ever exposed your cute, little body too?”

Biting my lip, I slowly nodded my head again and whispered, “Yes.”

She leaned in close, I could feel her warm breath against my cheek and ear, “That makes me very lucky and special. Casey, Sweetheart, why did you choose me?”

I stuttered and stammered for a bit before collecting my thoughts and explaining, “When we first met, you were really nice to me. We talked all night long.” I paused to swallow and try to clear my head. Her huge, warm hand was still slowly moving toward my rigid, pink erection. “Um, usually girls like you wouldn’t even look at me, much less talk to me.”

She squeezed my thigh gently and asked, “Girls like me?”

My back arched and I squirmed on her wide, solid lap, “Tall… pretty… smart girls.”

She leaned in closer and felt her lips brush against my neck below my ear, “You forgot strong.”

I whimpered softly and snuggled against her, “Yes, strong too.”

Her hand was close enough that her index finger was touching my little pouch of balls. I parted my legs to give her enough room to do, whatever she wanted to do. Turning my head so I could look at her, I whispered, “I’m really glad you didn’t laugh or get mad when I answered the door like this.”

She smiled and slid her hand up my naked back to rest on my neck. She gently pulled me toward her while whispering, “Seeing you answer the door like that was the best surprise I can imagine. And I don’t think I could ever be mad at you.” Our noses were touching when she next spoke, “I’m going to kiss you now.”

I whimpered softly when our lips touched. She kissed me gently several times before sliding her tongue into my mouth. With one hand behind my neck and the other so close to my desperate penis, I was in heaven. I slipped my skinny arms around her strong, muscular neck and tilted my head to the side a little. This allowed more of our tongues to dance together. We sat there for quite a long time kissing each other and not saying a single word. Ruby never moved her hand up high enough to touch my throbbing penis. Instead, she only slid her hand up and down between my legs, letting the side of her finger brush against my pouch.

Our make-out session eventually ended, but we remained close enough that our noses were touching and our lips brushed against the others. My arms were still looped around her neck and I couldn’t stop myself from giggling.

Ruby spoke softly, “I could get used to this.”

I whispered, “You could get used to what? Kissing me?”

She grinned and kissed my lips gently before answering, “All of it. Everything. Kissing you, having you sit on my lap naked, teasing your…” She paused mid-sentence and looked down at my erection. “Teasing your body. Teasing your penis.”

I giggled, “I could get used to this too.”

Her lips brushed against mine and I felt her warm breath on my skin. “I had planned on taking you to my apartment and fixing us lunch.”

I bit my lip and said, “I sent you naked pictures of me. And you were going to make me lunch?”

She smiled warmly and corrected herself, “Okay, I had planned on getting you to my apartment and hoped we’d wind up in a position like this!”

I whispered, “We can still do that. I’d like to be naked in your apartment.”

She kissed me gently and said, “I’d like you to be naked in my apartment too.”

This time I kissed her and whispered, “I couldn’t decide what to wear for you. Do you want to help me pick something out to wear for the drive to your home?”

She smiled and while I rose up off of her lap, she said, “Yes, but you’re not going to wear very much! If you have to wear clothes, they’re going to cover as little as possible. I prefer you to be naked.”

Ruby stood up and followed me to my bedroom. Together, we went through everything hanging in my closet, every drawer in my dresser and nightstand. After seeing everything I could possibly wear, Ruby made her choice. She had a playful grin on her face when she pulled out a pair of white flip-flops and dropped them on the floor in front of me. She then opened the bottom drawer in my dresser and took out a little white speedo. I’d bought the swimsuit with the intention of visiting a tanning salon, but the fear of skin cancer scared me off.

While holding the speedo on the tip of her finger, she said, “Here you go. If anyone says anything, I’ll tell them I’m taking you to the swimming pool.”

I shivered as I reached out to take the suit from her offered finger. I held the suit up between us and moaned, “I’ve never worn so little in public before.”

She smiled at me standing naked before her and said, “So this will be a treat for you. And perhaps sometime soon, I’ll take you outside wearing even less.”

Looking up into her eyes, I whimpered softly, “I think I’d like that.”

Bending over, I wiggled into the snug-fitting suit. As I stood up and pulled the stretchy material into place, the outline of my skinny erection was unmistakable. Anyone who looked at me would see the impression of my stiff penis. Ruby let me admire myself in the mirror on my closet door for a few moments before stepping in behind me. She reached around and cupped my stiff erection in the palm of her hand. Her other hand cupped my butt. She held all of my private parts in her hands!

While looking at me squirm under her touch in the mirror, she said, “The sooner we get going, the sooner we can get you out of this suit.”

I spun around and she held my hand while I stepped into my flip-flops. She continued to hold my hand as we made our way to my front door. On the table beside the door sat my keys, phone, and wallet. Ruby saw me reach for them and snatched them up first.

After letting go of my hand, she reached for the doorknob and asked, “Are you ready, Casey?”

I stood there and shivered while I squeaked, “Yes!”

Ruby opened my door wide. My penis throbbed in my speedo as I stepped out into the hall. No one was in sight and I stood there impatiently while she locked up my apartment. While holding my wallet, phone and keys in one hand, she took hold of my hand with her other. Together we casually made our way to the staircase.

We made it to the second-floor landing before we encountered anyone. An older woman I’d often run into while getting my mail opened the door into the stairwell at the same moment we stepped onto the landing. She stood there, frozen in place watching me wiggle toward her.

When I stood just in front of her, I bounced on my toes and giggled, “Hello Alice!”

Her eyes wandered over my pale, skinny body with the unmistakable lump of an erection in my tight swim trunks. She was staring at that lump when she uttered, “Hello Casey.”

Ruby spoke up while Alice devoured my body with her eyes. “Alice, is it? I’m Ruby, Casey’s friend. I’m taking him to go swimming. Doesn’t he look cute in his suit?”

I held my arms up out of the way and turned around in a slow circle so Alice wouldn’t miss a thing. Her voice sounded deep and raspy when she said, “Nice to meet you, Ruby. And yes, Casey looks very…” She paused to lick her lips before groaning, “…cute.”

Ruby reached down to take my hand, but she missed and her hand cupped my stiff erection instead. I giggled and arched my back. Ruby left her hand there and gently squeezed me. I squirmed under her gentle touch and loved that Alice was there to witness me being fondled.

Ruby looked down at me and said, “We better get going. That chilly pool water is what you need to calm down.”

Alice stood there with her mouth hanging open watching Ruby grope me right in front of her.

I smiled brightly and took her hand after she released my penis. Looking back at Alice, I quickly chirped, “Bye!”

Ruby walked down the steps while I hopped down them alongside her. Alice remained on the landing and watched us until we were out of sight. We didn’t run into anyone else on our way to her SUV. As we stepped out of my building into the midday sunshine, Ruby squeezed my hand and said, “You don’t know how badly I wanted to strip you of your suit in front of Alice.”

We continued walking while I admitted, “I wish you would have.”

She looked down at me while I looked up at her. Ruby was fully dressed and looking like she was on her way to the gym. While I rushed along beside her in flip-flops and a speedo. With a smile on her face, she said, “Don’t worry, I won’t let an opportunity like that pass by again.” We were quite a ways from her SUV when she stopped walking. I turned to face her to find out what was wrong.

After glancing around in all directions, she grinned and said, “Casey, give me your swimsuit.” She held out her hand, waiting for me to do as I’d been told.

I swiveled my head around quickly. We were just outside of my apartment building. People I saw everyday lived here. But this was Ruby. She was the only person who had ever shown a real interest in me. And there was no way I was going to let that slip away. Plus, I’d always wanted to be naked outside. This was the opportunity I’d always wanted. The sound of nearby traffic and a breeze blowing through the trees made me hyper-aware that I was outside.

Turning to face Ruby, I stepped out of my flip-flops onto the warm sidewalk. Looking up into her eyes, I hooked my thumbs into the sides of my suit. Glancing around one last time, I silently wished Alice would step outside, but she never did. I wiggled my hips and slid the swimsuit over my stiff penis and down my legs until it fell around my ankles. Ruby smiled down at me while I squatted to pick up my suit.

After handing her my speedo, a shiver shot through my body. Goosebumps rose up on my skin even though it was very warm outside. I looked up into her eyes and squealed, “Ruby, I’m naked!”

She grinned and said, “Yes you are. And you’re going to stay that way until I say otherwise.” Ruby held my speedo and my other things in one hand. She reached out and took hold of my hand with the other. My penis throbbed hard and its squishy pink head glistened with my excitement. As I moved to step into my flip-flops, Ruby pulled on my arm as she began to walk away. She said in a surprisingly casual voice, “Leave them.”

I had no choice. I left my flip-flops on the sidewalk and did my best to keep up with Ruby’s pace. As we approached her car, she pulled the key-fob from the waistband of her workout pants. She unlocked the car and opened the passenger door for me. Completely naked, not wearing a single thing, I stepped up into her SUV and sat my bare bottom down on the seat. My back arched uncontrollably and a soft moan left my lips while I watched Ruby close my door.

She walked to the back of the SUV and opened the hatch. I heard her moving things around and latches opening and closing. I looked back at her and our eyes met. She grinned and said, “I’m putting your things somewhere safe.”

Stepping back, she closed the hatch. When she opened the driver’s door, the only things she had in her hand were her own keys and her phone. She stepped up and sat in the car. As she did, the entire vehicle shifted under her weight. That movement made me feel safe. I knew in my heart she would never let anything bad happen to me. And she was strong enough to protect me from anyone or anything. I had honestly never felt so safe before.

She reached across my body, pulled the seatbelt down and buckled me in. She leaned in closer, kissed my lips and said, “Buckle up for safety!”

Ruby got settled in the driver’s seat and after buckling herself in, started the engine. She drove slowly and carefully out of the parking lot. Before she turned onto the street, I said, “I can’t believe we’re doing this, Ruby! I’m naked outside and we’re driving away from my building!” I fought with myself to keep from laying my hands on my desperate penis. I was so horny!