Wild Night for a Young Man

I paused while standing naked in the street right in front of Mrs. Thomas' home. Samantha slowed the car and then brought it to a halt directly behind me. The headlights lit up my nudity like a spotlight. Samantha was close enough that she didn't need to shout. She looked at the lit windows in her home. She told me it looked like Mrs. Thomas was still awake. I stood there silently for several moments. If there was one person I would feel completely safe with exposing my naked body too, it would be Mrs. Thomas. I knew for a fact she would love to see me in my birthday suit.

Samantha dimmed the headlights and called me back toward her car. I tiptoed back near the driver's side door. I stood between the car and Mrs. Thomas' home. Samantha asked if I wanted to go say hello. I nibbled on my lip while forcing myself to hold my hands behind my back. In a soft voice, I told her I did, but I couldn't just walk up there and knock on the door. Samantha's eyes wandered over my naked body, after a few moments a grin formed on her face. She had come up with a plan.

Samantha suggested I tell Mrs. Thomas that I'd locked myself out of the house and I was waiting for Samantha to come home from a night out with her friends and let me in.

A shiver shot up my spine and my penis jumped and throbbed. I whispered that it would probably work. Samantha told me she knew it would. But she told me not to do anything until she had driven the rest of the way home and parked the car. Before driving off and leaving me standing in front of Mrs. Thomas's home in my bare skin, Samantha told me to have fun.

I stood there watching Samantha drive away and didn't make a move until her headlights went out. Turning my attention back to Mrs. Thomas' home, I swallowed hard and began taking small steps toward her door. When I got close enough, I reached out and pushed the doorbell. I heard heavy footsteps approaching the door and then the porch light came on, casting my naked body in what felt like a spotlight.

I stared at the doorknob. When it turned and the door came open, I completely lost my breath. I felt as if I had been electrocuted. Every cell in my body was tingling and my stomach turned with shame. Mrs. Thomas was wearing slippers and a silky robe over her modest nightgown. Her immense breasts covered by so little material captured my attention. They rose and fell with each breath she took. And as her eyes zeroed in on my naked body with my very stiff penis being hidden behind my hands, I witnessed her thimble-sized nipples become stiff and jut out toward me.

In a deeper than normal voice, she asked, "Um, Karter, Sweetie, what happened to your clothes?"

I blushed and squirmed while standing on her doorstep. I was unable to look her in the eye. But I did stammer quickly, "I was just taking the trash out. I didn't mean to lock myself outside. Samantha is out with her friends and I don't know when she'll be home!"

She leaned against her door and said, "Oh my!" Her eyes were wandering over every inch of my exposed flesh. I felt so vulnerable and exposed.

Using every ounce of willpower, I slowly moved my hands away from my little erection and held them together behind my back. Blushing like crazy, I managed to look up into her eyes and say, "I didn't know where else to go. You're the only person I feel safe enough to come too."

Her eyes zeroed in on my throbbing erection and whispered, "Well I'm very happy to hear that. Sweetie, you can pop over here naked any time you'd like."

Standing there, blushing and rotating my hips from side to side while still holding my hands behind my back, I whispered in a soft voice, "Thank you, Mrs. Thomas. I knew you'd understand. I knew you'd be the only person to understand." I almost asked if she would invite me inside, but I stopped myself. I looked up at Mrs. Thomas and said, "I don't know if you remember or not. But we were interrupted at the last New Years party. You were kissing me, touching me and were well on your way to undressing me." My hand had slipped around and I began squeezing and stroking my erection on Mrs. Thomas' porch.

She watched me masturbate and moaned, "I was quite tipsy, but I do remember pieces of that night. And our time in the bedroom is something I'll never forget. But it's best that we were interrupted. If we hadn't been, I may have stripped you naked and done inappropriate things to you."

I looked into her eyes while still squeezing my penis between my fingers, "I think about that night a lot. I like to think what would have happened if we hadn't been interrupted."

She glanced up at my eyes and then her gaze drifted down to my fingers teasing my very excited penis. In a raspy whisper, she said, "I think about that encounter quite a bit too. I like to fantasize if I had my way with you that night, you'd now be living with me and not Samantha." She reached out and offered me her hand.

Biting my lower lip, I reached out and took her hand while she guided me into her home. As the door closed behind us, she kept hold of my hand and turned to face me. There was lust in her eyes. In that same raspy voice, she asked, "Would you like me to find you something to wear, Sweetheart?"

Biting my lower lip again, looking up into her eyes I answered, "No thank you. I'd like to stay naked, if that's okay with you."

She stepped closer to me, backing me against a wall. Her lips were so close to mine when she spoke, "I most definitely want to keep you naked."

A soft moan slipped through my lips when Mrs. Thomas stepped closer to me. So close that my desperate penis touched the material of her robe on her thigh. Between heavy breaths, she said, "Sweetheart, I think we should call Samantha and let her know what has happened. If you were mine, I'd be worried sick if I came home and you're weren't there."

I nodded my head slowly while shifting my hips forward so my penis made more contact with her robe-covered thigh. Very slowly, I began to slide my penis up and down on a small area of her leg. "I suppose that's a good idea. Would you call her for me? I think this will all sound better coming from you."

Mrs. Thomas leaned in so her lips brushed against mine while she spoke, "Of course, Sweetheart. I'll be happy to make that call."

I was so horny and feeling so naughty, I nearly squirted on her robe when Mrs. Thomas's lips met mine. Her considerable arms circled my waist and pulled me against her soft, warm body. Her tongue entered my mouth and began a slow, erotic dance with my own. With my arms around her neck, one of her hands slinked down my back until she held my naked butt in her palm. I whimpered into her mouth while we continued to kiss for several moments.

When our lips smacked apart, I giggled and said, "That is exactly how you kissed me last New Years Eve! Except you tasted like champagne and you were touching me over my clothes."

Her eyes focused on mine and in a perfectly serious voice, "And if we hadn't been interrupted, I would have stripped you naked, just like you are right now."

I couldn't maintain eye contact and glanced away quickly. But I did eventually look back into her eyes and whisper, "Well, I'm naked now."

Leaning in close enough for her lips to brush against mine while she spoke, "That you are, Karter. And you're even cuter than I imagined." She leaned back and her eyes wandered up and down my body before leaning in close, "I love your complete lack of body hair. It makes you look so innocent. Was that your idea, or Samantha's?"

My voice cracked when I said, "Samantha's. It was her idea. She has been helping to shave me once a week for almost a year. She likes me to be hairless."

Mrs. Thomas grinned down at me and whispered, "I'm sure she does. And I must say I like you without hair too."

There were a few seconds while we stood there looking into each other's eyes. My little penis was throbbing and I'm sure it was leaking onto her robe. I was terribly horny after all that I'd been through that night and being in her presence without a thing covering my naked and hairless body.

Mrs. Thomas soon offered me her hand once again and I took it in my mine. Just like Samantha, my hand looked tiny compared to Mrs. Thomas's. She led me to her living room and after sitting on a large, comfy chair, she pulled my naked and very horny body down across her lap. She rested one of her large, warm hands on my upper thigh while picking up her phone with the other. I leaned back against the armrest and snuggled against Mrs. Thomas's soft body.

After being prompted, I called out Samantha's cell number, digit-by-digit while Mrs. Thomas dialed. It took several rings, but Samantha eventually picked up. Being perched on Mrs. Thomas' broad lap, I was close enough to hear her voice over the phone. And the background noises I heard from Samantha's end of the call sounded like she was in her car. She really was going out with her friends.

"Hello Samantha, this is Deborah Thomas from down the street."

Until that moment, I had no idea what Mrs. Thomas's first name was. I smiled and nuzzled against her body while she spoke with Samantha on the phone.

Samantha responded, "Hello Deborah, is there something I can help you with?"

Mrs. Thomas's hand slid further up my thigh until the sides of her fingers were brushing against my little pouch of marbles. I squirmed on her lap and pushed myself against her touch. "Well Dear, I have just had a lovely surprise. Karter appeared on my doorstep."

"He did? Is he okay?" Samantha did a fantastic job of sounding concerned.

"Oh yes, he is fine. But he somehow locked himself out of your house."

Samantha chuckled, "He did the same thing last week. He can be so helpless at times. Is he being any trouble? I can come home right now if he is."

Mrs. Thomas grinned while laying her open palm over my rigid penis. "Oh no, not at all. You know how much I enjoy his company!"

Samantha quickly replied, "You two do have a very special relationship." She paused for a second or two before asking, "Deborah, what was Karter wearing when he arrived at your door?"

Mrs. Thomas left her hand over my penis and it throbbed against her palm. "That's the funny thing. He was naked and terribly embarrassed. I brought him inside and offered him something to wear right away."

Even though Samantha knew how badly Deborah wanted to get me naked, she sounded perfectly sincere when she said, "I'm so sorry you had to see him like that. This is going to sound terrible, but months ago, I learned that Karter liked the idea of people seeing him naked. After I learned that, I began to forbid him from wearing clothes while we're at home."

Mrs. Thomas silently kissed my forehead before saying, "For Heaven's sake, there is no need to apologize. If the boy wants to be seen naked, perhaps I should keep him that way until you pick him up later tonight."

Samantha quickly said, "I think that is a fantastic idea. And if you don't mind keeping an eye on him, I'll be in no hurry to rush home."

Her hand simply sat on top of my penis. It didn't move at all. But her soft, warm touch felt magical. "I don't mind watching over him at all. As a matter-of-fact, I'd be happy to watch him any time you need to go out with your friends. Just drop him off on your way out!"

Samantha giggled, "Are you offering to babysit him?"

Mrs. Thomas giggled too, "I suppose I am."

Samantha replied, "That is so nice of you. When I do go out, I always wind up leaving my friends much earlier than I would like too. Karter has never liked to be left alone for very long, especially at night."

Mrs. Thomas squeezed my stiff penis and asked Samantha, "Is the poor boy afraid of the dark?"

"He is afraid of the dark, but he is also afraid of being left alone at night. It all stems back to how his mother left in the middle of the night when he was just a child."

I bit my lower lip and snuggled back against Mrs. Thomas all the more. The story Samantha had shared about my mother was true. She snuck out of my life in the middle of the night when I was in the 2nd grade. Ever since that night, I've had trouble dealing with the dark and being left alone. Thankfully, Samantha thought my fears were cute and did her best to rarely leave me alone at night. But hearing her say that she always left her friends early because of me rang true. And realizing that made me feel terribly guilty.

Mrs. Thomas changed the hand she was holding the phone with so she could wrap her arm around my body. She embraced me warmly while saying, "Samantha, why don't you stay out as long as you'd like. Don't worry about Karter one little bit. I'll take good care of him. If you'd like, he could even stay the night and I'll bring him home in the morning."

"Deborah, you are a saint! I was just about to drop my girlfriends off at a new club that is supposed to have the best male strippers in the city."

Mrs. Thomas squeezed my body against hers, she knew I'd heard what had been said.

Samantha sounded truly excited, "If you're absolutely sure, I would love to take you up on your offer."

Mrs. Thomas smiled and said, "I'm very sure. And it is no trouble at all. I'll bring him to you in the morning after I've fed him breakfast."

Samantha replied, "If it's really no trouble. Would you mind keeping him until I call tomorrow? Knowing he's safely in your company, I may indulge a bit."

"I don't mind at all. I'll be happy to watch him anytime. Have a good time tonight and we'll see you tomorrow."

The call quickly came to an end. After setting the phone down on the end table, Mrs. Thomas wrapped both her arms around my body. Her lips brushed against my ear while she whispered, "Not only am I your official babysitter, I have Samantha's permission to keep you naked all night long."

I whimpered softly and moaned, "I heard."

Her lips continued to brush against my ear when she said, "I have a feeling I'll be babysitting you on a very regular basis. And now you'll not only be forbidden from wearing clothes at home, but you'll also be naked in my home as well."

I squirmed on her lap. "I'm really happy I came over here, Deborah." As her name left my lips, it felt odd and I immediately regretted using it.

"I'm very happy you knocked on my door too, Sweetheart. But I want you to continue calling me Mrs. Thomas. I am your babysitter after all."

I giggled softly and whispered, "Yes, Mrs. Thomas. I'm sorry, Mrs. Thomas."

She hugged me warmly and after glancing at the clock, said, "Karter, Sweetie, it's getting late. I think it's time we get ready for bed."

As I slid off her lap, I said, "If you say so. You are my babysitter." As the last word left my lips, I stood up in front of Mrs. Thomas. My skinny, four-inch erection was pointing at the ceiling and glistening with the excitement it had been leaking all night.

Mrs. Thomas sat there looking at me for a few moments before she too stood up. Dragging her fingernail along the underside of my overly stimulated penis, she asked, "Do you usually bathe in the mornings or evenings?"

A shiver of excitement shot to the very core of my body. "It depends. Sometimes I do it in the mornings and other times I do it at night."

Taking my hand in hers, she said, "I'm sure you'll sleep much better if you're squeaky clean." And she led me up the stairs to the second floor of her home. She guided me down the hall to the last door which turned out to be the master bedroom. The giant 4-poster King bed dominated the room. Although every piece of furniture was made of the same dark wood. The bed had a perfectly, snow-white comforter and at least a dozen pillows. The ornately carved, vertical columns on each corner of the bed were massive, bigger around than my thighs and nearly touched the ceiling. It was a bed suited for a queen.

The walls of her bedroom were painted a dark red, but textured with white to soften the color a little. The dressers and bedside tables were decorated with items an older woman have. Perfume bottles, old photographs, candles, and a large jewelry box. It was a very warm and romantic room.

But Mrs. Thomas guided me across the room into the master bathroom. That room was painted a soft green with white tile on the floor. After turning on a switch, the light fell from behind a partial wall. I was sent around that wall to find a very large, completely tiled, walk-in shower. On a small shelf were all the items one would expect to find in a mature woman's shower. To the side of that shelf was a built-in bench.

Mrs. Thomas sent me in to shower with a pat on my bottom. She told me she would check on me in a few minutes. So I adjusted the water and was soon trying to decide which shampoo to use when something happened that completely knocked the wind out of me. Mrs. Thomas came around that partial wall to join me in the shower and she was naked! She stood just out of the spray of water and let me look at her for several moments.

My mouth fell open and my penis throbbed wildly. Mrs. Thomas was an ample woman. Light blue veins could be seen through her pale skin on various parts of her body. Her shoulders were broad. Her enormous breasts were easily the size of cantaloupes and her dinner-plate sized nipples were angled slightly downward. Her belly rolled over but didn't come close to hiding her bushy, black forest of pubic hair. Her hips swelled out to balance her thick thighs. She was gorgeous.

After giving me enough time for my eyes to wander over her body several times, I whispered, "You're beautiful."

She smiled and stepped closer to me. She didn't hesitate to choose the most feminine and flowery scented shampoo from her collection. While filling her palm with the pink liquid, she smiled warmly at me and said, "Thank you, Sweetheart."

After working the shampoo into a thick lather between her hands, we switched places so she stood under the spray while she reached out and began to wash my hair. Her fingernails drug along my scalp and brought goosebumps up all over my body. I wanted to touch her. But it didn't feel like I should. So I stood there with my hands at my sides while she scrubbed my scalp.

Once my hair was covered by a mountain of suds and they began sliding down my face, she rinsed off her hands and picked up a bottle of equally feminine body wash. While keeping me out of the spray, she sat on the bench and began to wash my arms, shoulders, chest, and back. Still covered in suds, she had me brace myself against the wall while positioning one of my feet between her spread thighs. Through the suds oozing down my face, I got a brief look at her bushy pussy before I had to close my eyes to protect them from the soap.

Mrs. Thomas washed my toes, foot, shin, knee and up my thigh before switching to my other leg. She repeated that same process with my other leg, leaving me perfectly clean except for the ring around my hips.

In a raspy voice, Mrs. Thomas uttered, "Karter, Sweetheart, I am your babysitter, am I not?"

I blew bubbles from my lips before answering, "Yes, Mrs. Thomas."

Quickly peeking out from behind the bubbles I saw she began to slowly slide her hips closer to the edge of the bench. "As your babysitter, you must do as I say. I make all the rules, do I not?"

When I reached up to wipe the bubbles from my eyes, Mrs. Thomas stopped me. So I stood there with my eyes closed and said, "Yes, Mrs. Thomas. You make all the rules."

"You're such a good boy." Her voice changed then, it became firmer, more strict sounding, "Karter, get on your knees."

A soft moan slipped from my lips. And I didn't hesitate for a second before I slowly descended to my knees, right between her legs. Her fingers from both hands slid through my sudsy hair until she held my head in her hands. She then slowly pulled my face between her thick thighs. Her musky, pungent aroma filled my nose which caused my mouth to water, my penis to throb and the wrinkled hole between my cheeks to quiver and flex.