Becoming Joey

"Joe!" My mother shouted from downstairs. I paused mid stroke, then ignoring her, continued to slide my hand up and down my shaft.

"Joey!" She was more insistent, obviously not going to go away. I slid my underwear back up over my still hard cock. It might not have been big by porn standards, but on my slight 5'6" 130 lbs frame, it looked big.

"Yeah Mom," I shouted, mostly to keep her from opening my bedroom door.

"Come down here please. We need to talk about something."

"Great," I thought, "I wonder what this is going to be? Get a job...are you going to college?" It was June and I was 18. I just graduated from high school and I do have to admit that I didn't really have any direction. My goals for the summer were to hang out with my friends, smoke pot and hopefully finally get laid, although I didn't really have many prospects to achieve that final goal. I was a decent looking guy. Blond hair, blue eyes, thin but toned. I had very little body hair and what I had was blond and light. I just wasn't a big guy. I kept waiting for that growth spurt that my parents always promised, but it never came. Now I was just a short, cute, slightly effeminate guy.

I had dated a few girls in high school, but had never really gotten past second base. I had a few make out sessions in the back seat of my car, but never even got to go under the shirt.

"Coming," I shouted. I pulled my shorts up and promised myself I would finish what I started soon. I masturbated 2 or 3 times a day anyway so skipping this one would just make my next session that much better.

My mom was sitting at the kitchen table. At 36, she was a good looking woman and to be honest, I supposed I took after her. She had to dye her hair to keep it blond now, but she was short and slight, but with breasts that looked too big for her body.

"Joey, I just got a call from Mrs. Williams down the street." My cock thickened again at the thought of Mrs. Williams. Probably around 40 years old. She was tall and statuesque. Her breasts always spilling out of her too small tops that she wore and her tight shorts showed off her long lean legs. I'd heard my mother gossip about her in the past. I guessed it was just jealously.

"Yeah?"

"She and Mr. Williams are going to be taking a week cruise this summer and they are looking for someone to watch Dingo, their dog and take care of the house. She thought of you and was wondering if you didn't have anything to do this summer, if you would be interested. They'll pay you."

I thought for a moment of being alone in their house, my mind immediately thinking of finding her lingerie or who know what else. "Sure, I could use the money."

"Good, because I already told her yes for you. They are leaving next weekend and she like you to come over Saturday to go over what needs to be done. They want you to spend the night. They will be out all night and they thought it would be a good dry run to see if you have any problems."

"OK, Mom."

On Saturday, I showered and got dressed. I packed an overnight bag, which included some video games, a couple porn magazines and of course some lube. Mrs. Williams asked me to arrive at 4 and at 3:45, I pulled my red Pontiac Grand Prix into their driveway. I grabbed my bag and knocked at the front door.

Mrs. Williams answered, wearing a sundress that did little to hide her stunning body. I found myself staring at her chest, when she cleared her throat. I blushed and looked up at her and saw a wry smile on her face.

"Hi Joey, we're so glad that you can help us out this summer. It's hard to leave our house and Dingo to just anyone."

"I'm happy to help out Mrs. Williams."

"Please, you're 18 now, aren't you?"

"Yes"

"Well, we are all adults, you can call me Susan now."

"Yes, Ma'am...I mean Susan."

"Well, I think I like that even better."

I must have looked confused.

"Calling me Ma'am, I like that. Let me have a look at you. You are still so cute. I bet the girls love you."

"I don't know about that."

"Well don't you worry," she said, putting her arm around me and guiding me into the house. "If they aren't now, they will be. Come on, let me show you the house and introduce you to Dingo."

Mrs. Williams guided me into the kitchen. At the back door, a large golden retriever jumped against the glass. She opened the door. Dingo rushed at me, knocking me back and proceeded to lick my face. "I don't think there will be any problem with you two getting along." She pulled the dog off me, giving me a chance to gain a bit of control over myself. I stood and leaned down to scratch his ears. His tail wagged furiously and his tongue lolled out of his mouth.

"I love dogs. I'm looking forward to watching him."

"Good, now let me give you the tour." She showed me around the downstairs, giving instructions as we went. We then went upstairs. "This is where you'll be sleeping." She opened the door to a guest room with a nice 46" flat screen on the wall and a DVD player attached underneath. The room was decorated in different shades of pink, with frilly white curtains. On the credenza was an assortment of teddy bears. They were definitely planning on having more female guests than male. "We have the tv and the DVD player in here if you want to watch any movies as you are going to sleep."

She winked at me. We backed out of the room and started back down the hall. As we were about to start down the stairs, the door to the master bedroom opened and Mr. Williams came into the hall, wearing only a towel around his waist.

"Sorry, Joey, this is Matt, my husband." Matt reached out his hand to shake mine, but had to stop to grab the towel that was slipping from his waist. Matt towered over me. He had to be at least 6'3". His body was tanned and toned. His chest had the same dark hair as his head, which trailed down and disappeared under the towel.

"Sorry about that," he said, sheepishly, "I didn't know you were here yet."

"It's okay," I said, still not able to take my eyes away from him. I thought a saw a slight bulge pulse under the towel, but told myself that it had to be my imagination. Susan laughed. She touched his bare shoulder with her left hand, then leaned in to whisper in his ear. Her right hand grazed across the front of the towel. There was no mistaking the pulse now. He smiled at me.

"Matt is not very fond of clothing. I hope that we haven't scared you off."

I swallowed, unsure of what to say, then, finally, looking down, said, "No, Ma'am".

She softly touched my arm. "Good. We are trusting you with all our possessions. We should all feel comfortable around each other. Now, if you'd like to go downstairs or to the guest room to get settled in, Mr. Williams and I need to get ready for the evening."

They retired to the master bedroom. I went downstairs to get my bag and brought it back up to the guest bedroom. I could hear their voices in the bedroom as I walked down the hall.

"She would be so cute, wouldn't she?"

"I can't believe you touched my cock out there."

"I just had to see the reaction."

"How are you going to do it?"

"Don't you worry about it. I've been watching him for a long time."

Then the voices stopped. I continued my way to the guest room. "I wonder what that was all about," I thought. I did notice that my cock was hardening, pushing down the leg of my shorts. I hoped it would go down before they came out. I wandered downstairs and went out the back door. Dingo was immediately on top of me, a tennis ball in his mouth. After prying the ball from him, we spent the next half hour with me throwing the ball to the end of the yard and Dingo racing after it.

"Joey"

I turned. Matt and Susan were standing the in doorway. Matt was wearing a black suit that was obviously tailored. Susan was wearing a red dress that came down only to mid thigh. It was low cut and her breasts were spilling out of the top.

"Wow, you look beautiful."

"Why thank you Joey. It is always nice to be appreciated." She gave me a kiss on the cheek. "We are ready to go. I've left our cell numbers on the fridge. If you have an emergency, please don't hesitate to call. I've left $40 on the table, if you'd like to order pizza."

"Thank you, I'm sure everything will be fine."

I walked them to the garage door. "We'll be home around 11 tomorrow morning. Thank you so much for doing this for us." She kissed me on the cheek again, lingering a moment this time. I watched as they pulled out of the garage. The door shut behind them. My cock was aching. I immediately ran up the stairs to the guest room. I fumbled with the remote, finally getting the TV on and rummaged around my bag for a DVD. I slid the DVD into the tray and pushed start before flinging myself on the bed. I worked my shorts down my legs. Pre-cum already formed a wet spot on my underwear.

The video came on. It was nothing fancy, just an amateur porn that I had liberated from my father several years ago. I was looking for one scene. A couple with a third younger guy. The scene started with the woman (who I now thought looked a lot like Susan) bringing a glass of lemonade to the young man cleaning her pool. She was wearing a thong bikini.

I rubbed myself through my underwear, feeling the wet spot grow. On the video, the woman encouraged the pool boy to take a break. She sat him on a chaise lounge and rubbed suntan oil on his now glistening skin. She feigned surprise at seeing the bulge in his shorts, but quickly overcame it and went to her knees. She extracted the large cock from his shorts as I extracted mine. My cock head was completely soaked. I ran my fingers lightly around the head, then brought my fingers to my mouth. I licked the pre-cum from my fingers as the actress took the pool boy's cock in her mouth.

My cock pulsed as she took him deep into her throat. Her bikini top by now had hit the ground. The pool boy reached down and fondled her D cup tits as she swallowed his cock. The camera panned out and in the doorway, her husband could be seen watching from the shadows. His cock was outlined by his tight shorts. She didn't notice, being completely focused on the cock in front of her. He walked towards her, his shorts coming off as he walked. She was on her knees, he ass sticking out. He pulled the string of the thong aside and in one stroke, buried himself deep in her pussy. Her mouth opened in a gasp and the pool boy took the opportunity to shove his cock deep into her throat.

I watched the video, stroking my cock, but my mind went to Susan and, to my surprise, Matt. I felt myself getting close and increased my speed. Finally, with a loud moan, I came. I cupped my hand at the head of my cock and caught most of my cum in my hand although some dripped down on the bedspread. I brought my hand to my face, looking at the large load, the slowly licked my hand, feeling the cum spread in my mouth.

Finally sated, I pulled my shorts back on, leaving my underwear off and went off to explore the house. The house was large, 3500 square feet by my guess. It was decorated in a contemporary manner, but it was obvious that the furnishings were expensive. I found the door leading to the basement. The basement was finished with a pool table, big screen tv and a wet bar. I checked out the bottles on the bar, before deciding to pour myself a jack and coke.

One door led into a storage area. Another door on the far side of the room was locked. I searched in vain for a key, but to no avail. I amused myself hitting balls around the pool table for a bit, before heading back upstairs to feed Dingo.

That evening, with a pleasant buzz from several jack and cokes, I laid on the couch in the basement, Dingo by my side and flipped through the channels on the tv. Restlessly, I rose and continued my exploration of the house. I checked out the other bedrooms, finding another guest room that appeared to be decorated much more generically. I cautiously opened the door to the master bedroom.

I closed the curtains and flipped on the light. I opened the closet door. Susan's clothes were all neatly hung on the left. Everything appeared to be ultra feminine. Matt's suits and casual clothes hung on the right. I backed out of the closet and opened the top drawer of the dresser. Susan's panties, all very neatly arranged. I wanted to pick them up, but knew that I would be unable to replace them in the same position. Then, looking at the bed, I saw them. A pair of panties that she must've worn today. I picked them up and brought them to my nose. They were still damp and I could still smell her essence on them. Unsure of what came over me, I quickly removed my shorts. As I stepped into her worn panties, my cock immediately hardened. I pulled the panties up over my cock, the head sticking out the top. I rubbed myself, feeling the silky lace strain with my erection. I stood in front of the full length mirror, checking my ass out in the panties. "I really do have a girl's butt," I thought, running my hands over it.

I left the panties on and put my shorts back on. It was time to take Dingo for a walk. All around the block, Susan's panties caressed me and a growing pre-cum spot mixed with Susan's juices left there earlier.

I couldn't believe how excited I was wearing her panties. My cock swelled with each step and I found myself moving my ass differently as we walked through the darkened neighborhood. Once back and Dingo safely put to bed, I returned to the master bedroom. I didn't dare touch the panty drawer, but found a variety of negligees in the closet. I picked one that matched the black panties and slid it over my body. My nipples immediately hardened at the touch of the silk. Once again, I posed in front of the mirror, marveling at how sexy I looked.

I returned to the drawers and searched in the lower ones, finally finding a drawer that held a few vibrators, as well as a realistic dildo attached to a harness. Not knowing what was coming over me, I picked up the dildo. It was about 8" long and about as thick as my own cock. I rubbed it against my silk clad cock, moaning at the touch, then slid it lower until the head rested just under my balls. I gave a slight push and felt the head, through the silk, push against my ass. I laid on the bed, and pulling the panties to one side, felt the tip against my hole. I grasped my cock then and furiously stroked it through the fabric of the panties, cumming almost immediately. I watched the cum seep into the panties as my breathing returned to normal.

I carefully returned everything to it's proper spot, then rinsed out the panties in the sink. I stumbled to the guest room and fell asleep almost immediately, thoughts of pretty things and big hard cocks filling my head.

Dingo's howling woke me in the morning. I got up and let him out and fed him. I made one more pass through the house to make sure that everything was in it's place. I could wait to have a whole week to explore my new found passion.

I was sitting on the couch with the TV on when I heard the garage door open. A few moments later, Susan came through the kitchen door.

"Hi Joey, did everything go alright last night."

"Yes Ma'am, no problems. Dingo and I got along just great. Where's Mr. Williams?"

"Oh, he just had to run to the store. I asked him to drop me off since there was something that I wanted to talk to you about."

She came and sat beside me on the couch. "I want you to stay relaxed Joey. I told you to make yourself at home and it seems that you did." She held her phone in front of me and gestured for me to look. I glanced down at the phone and immediately saw myself laying on the bed in the guest room, my shorts around my ankles, stroking my cock. She paused the video at the point where I was lifting my hand to lick my cum.

"Mrs. Williams, I'm sorry. I never meant for you to see that." Susan put her arm around me, drawing me close.

"Shhh, it's just us Joey. I have more for you to see. I'm sure that you can imagine what it is. Tell me, do you always eat your cum when you masturbate?"

"No Ma'am, that was the first time. I don't know why..."

"Joey, I think we've gone beyond the point of lying to each other. How often do you eat your cum?

I paused, looking down. "Pretty often."

"Good boy"

"Now, let's look at the next part. This is my favorite." The video showed me picking up her panties and sniffing them, before sliding them over my cock.

"What were you thinking about while you were wearing my panties?"

"I'm not sure. They were just so pretty and felt so good. It's kind of like I wasn't thinking at all."

"I understand that Joey." I felt her breast pushing against my arm. "I imagine it was almost like an out of body experience."

"Yes Ma'am. I just stopped thinking. I understand that you probably don't want me to watch Dingo during your cruise, but please just don't tell my mom about this."

"Nonsense, I see no reason that you shouldn't watch Dingo. This is going to stay between us. I have to say that I was a little turned on watching you wear my panties. What would you think of having free reign over wearing anything in my room while we are on the cruise, of course, knowing that I will be seeing everything?"

"It was just a one time thing Mrs. Williams. I'm sure that it won't happen again."

She reached her hand into my lap and brushed it slightly. My embarrassment caused my cock to shrink to nothing. "I certainly hope that's not true."

She kissed my forehead. "You have such a lovely ass, Joey. I would've loved to see you go further with that dildo. Did you want to fuck yourself with it, Joey?"

I gasped at hearing her say fuck and couldn't answer her.

"It's okay Joey dear. Just think about how it felt. You better get going now. We'll see you next Saturday."