Tom's Adventures Ch. 04

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Tom's Sister and her friend take him to the mall.
4.9k words
4.65
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Part 5 of the 7 part series

Updated 10/17/2022
Created 08/20/2006
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Suzy and Emily take Tom to the mall the following afternoon. They talk him into dressing up as a girl and then dare him to buy some lingerie. What happens in the lingerie store is amazing!

***

Chapter 4: Trip to the Mall

I woke up because someone was pulling on my dick. I opened my eyes and my sister was standing in front of me. I moaned and closed my eyes because the light hurt them.

"C'mon, get up! I need help cleaning the house from the party last night," she said.

I opened my eyes suddenly remembering the action that happened last night.

I looked at my sister. Her breasts were practically in my face as she leaned over me. She was still naked! I looked up at her face. Her blonde hair was a mess, but pulled back with a scrunchie. I suddenly remembered where I was.

I was spread out on the couch in the basement. I had fallen asleep there. I looked around and we were the only one's left in the basement.

"Where is everyone," I asked.

"Emily's upstairs cleaning the kitchen. Everybody else had something to do and had to leave," she replied as she stood up.

My sister looked gorgeous. She was the stereotypical blonde college cheerleader. I looked at her 22 year old body and the memory of what she and I did came back to me. My dick twitched.

I felt a pain in my dick. I adjusted my member as I stood up. I felt where my penis was chaffed from all the action it had last night.

"What time is it?" I asked.

"It's after ten. I want to start my list of chores now, so I don't have to do them in a rush before Mom and Dad get home tomorrow night. Will you help with the cleanup from the party?"

"Sure, let me go take a shower to finish waking up." I picked up a pile of towels that she had made at the bottom of the stairs and started up them.

I dropped the towels on the floor of the laundry room and went into the bathroom to relieve myself. The memory of what my sister and I did kept coming back to me. I started feeling a pang of guilt in my head. "She started it. She could have said 'No' at anytime," I thought to myself. I flushed the toilet and left the bathroom.

As I walked to the stairs, I looked in as I passed the kitchen. Emily was on her hands and knees cleaning the kitchen floor. Her shoulder length brown hair was falling over her face. I stood in the doorway and watched her naked ass wiggle as she scrubbed spots on the floor that someone had spilled something. She occasionally pushed her hair out of her face with her hand and then went back to work.

I walked into the kitchen, towards the refrigerator. I stepped over Emily. "Careful, I just washed that area," she said to me.

"Thanks for the warning. I just need something to drink."

"I was afraid to wake you up. You looked so cute sleeping."

I opened the fridge and pulled out the jar of apple juice. I looked at Emily as she continued scrubbing a spot. She looked up at me as I took a swig from the jar and placed the jar back in the fridge.

"You shouldn't drink directly from the carton," she said.

"OK. Thanks for the advice, Mom," I replied.

"Hey, now! Be nice!" she giggled.

I stepped over her again as I walked out of the kitchen. I turned and pinched her bare ass. "Ow!" she giggled. She stood up and whipped me with the towel she was using. It hit me right above my semi-hard dick.

As she moved to strike again, I turned and ran out of the kitchen while holding my now-in-pain cock. She chased me part way up the stairs before she turned around. I stopped at the top of the stairs, expecting her to come up after me. When she didn't appear, I walked down the hallway to my bedroom.

I closed the door to my bedroom behind me and walked to my dresser and pulled out some underwear, a pair of shorts and a t-shirt. I then walked to the bathroom.

The bathroom separated my sister's room and my room. The door to her room was open. I closed it, but not all the way. I turned the water to the shower on. I went and looked in the mirror. I saw old lipstick all around my face from where one of the girls ("Ladies now?" I thought to myself) had kissed me. I didn't realize any of them had worn any lipstick. I popped a blackhead that was at the edge of my hairline.

I then turned and climbed into the shower. I lathered up my hair and then stood with the hot water running down the back of my neck and back. I grabbed the washcloth that was on my rack and soaped it up. I bumped my sister's luffa sponge and it fell to the floor of the tub. As I bent down, I dropped my washcloth. I then reached out for the luffa and the washcloth and my shoulder knocked my sister's body wash off the edge.

"God, why do women need all this crap in a shower?" I asked aloud.

"Then we wouldn't look as beautiful as we do for you men," I heard a voice reply.

I stood up quickly and rinsed the shampoo out of my eyes. I pulled the curtain aside and Emily was sitting on the toilet next to the shower. She looked up at me as I looked down at her.

"Your sister said you were going to take a shower. I thought that it was a good idea."

I giggled to myself and smiled. I closed the curtain and continued washing myself. As I began washing my dick, I felt the bruising from the workout he got last night. I also ran my hand over my pubic area. I remembered the feeling as Jessica had shaved it last night. It felt awesome shaved. I decided then that I would have to keep it bald. I felt cool air enter the shower.

I turned and Emily stepped into the shower with me. I quickly got under the water and rinsed off. She came up behind me and started rinsing my back off with her hand. I turned to her, "Thanks." She was smiling at me.

I put my hands on her hips and moved around her, pushing her under the water. The water started running down her back. She leaned her head back into the water and ran her hands through her hair, wetting her head. She arched her back for me as she did this. Her breasts pointed straight out at me. I felt my dick begin to stiffen.

Emily then took the shampoo from the ledge and began lathering her hair up. She then took the body wash and luffa and began washing herself. I just stood there and watched her. "Will you wash my back?" she asked, handing me the sponge.

"Turn around," I said as I took the sponge. She did.

She bent forward a bit at her waist and I soaped up her back real well with the sponge. I started at the shoulders, sometimes reaching over her shoulders to the top of her breasts. Then I worked my way down her left arm. I went back up to her shoulder and reached under, soaping up her armpit. I then moved across her shoulders and repeated the process.

I then moved back to the middle of her back. I washed down her spine and then around her entire back in circles. As I reached her ass, I soaped up each ass cheek individually. I then reached under her as far as I could and ran the sponge over her pubic area.

I pulled the sponge towards me, over her cunt and asshole. I continued up the crack of her ass. She then turned around and said, "Thanks, I needed that." She took the sponge from me. She then rinsed her hair out and rinsed off.

I pulled the curtain aside and stepped out of the shower. I began drying off with a towel that was above the toilet. I looked in the shower and Emily was putting conditioner in her hair.

"Why do you do that?" I asked

"Do what?"

"Put that crap in your hair?"

"It's supposed to prevent split ends and my hair from drying out," she said.

"Yeah. I thought the anti-aging drugs women took did that," I said with a grin.

"What anti-aging drugs?" she yelled over the water. Obviously this was another attempt at sarcasm of mine that was lost on Emily. I pulled a new towel from under the sink and put it on the back of the toilet. I wrapped my towel around myself and walked into my bedroom.

My sister was there rummaging through my closet. I looked at her ass as she flipped through my shirts. "Can I help you find something?"

"I'm just looking for a nice shirt to wear. Emily and I are going to the mall since we didn't go yesterday."

"Oh, so I'm supposed to do all the cleaning myself?" I asked as I began putting on the pair of boxers underneath my towel. My sister turned to look at me.

"Oh, c'mon, big brother. You fucked me this morning, you can show me your package. Why're you hiding it behind the towel?" She moved over to me and yanked the towel from around my waist. I couldn't think of anything to say so I said nothing.

"We want you to come to the mall with us. We'll do the cleaning when we get home tonight and tomorrow morning. We just have to heavy clean the basement. I started laundry and Emily did the kitchen this morning."

"OK, that would be great. I need to get some new shorts for camping later this week anyways." I began putting on the t-shirt that I had taken out.

I had completed my "chore list" yesterday by mowing the lawn and weeding the flower beds. I only had to "spring clean" my bedroom and I was going to do that while I packed for a camping trip I was going on.

"You are NOT going to wear THAT if you go with us!" She exclaimed. Emily then walked into the room with a towel wrapped around her head.

"Does he still need his mommie to dress him?" Emily asked.

"NO!" I replied with a pissed off tone.

"He has no sense of fashion style. Look at what he was going to put on to go to the mall with us."

"You can't wear THAT to the mall," Emily said.

"OK then! There's my closet! You tell me what to wear," I said getting pissed off. Emily and my sister turned to look in my closet. I could hear them whispering to each other. I looked at their white asses as they flipped through my shirts. My sister left the closet and went to my dresser.

"I have an idea," Emily said and she ran through the bathroom into my sister's room. My sister pulled out a pair of khaki shorts. I looked at my alarm clock. The time was seven after eleven. It felt like it was three pm.

Erin walked back into my room and asked my sister to follow her. My sister had a curious look on her face as she followed Emily from my room to hers. I lay down on my bed and closed my eyes. I was still tired.

My bedroom door burst open and my sister walked in with Emily right behind her. Here, we want to wear these to the mall with us! She threw me a pair of panties and a matching bra. Emily was holding a pair of sandals and a summer dress.

"You want to me dress in THESE things? NO WAY!" I said.

"If you wear these, I'll spring clean your room for you," Suzy said.

"If you dress in this outfit, I'll be your slave when you get back from camping," Emily said. Emily then laid the outfit down on my dresser and walked over to my bed. She bent down and started kissed my stomach through my t-shirt.

I sighed. "If I wear this outfit, you guys have to wear skirts or a dress with no bra or panties." They both agreed and went into my sister's room to find something to wear.

I took off my boxers and t-shirt. I slid the panties up my leg. They were pretty tight on me. My now erect cock stuck out from under the band. However, the silk of the panties felt awesome. I moved my hand over my ass and pubic area examining the silky feeling.

I then picked up the bra and slid my hand through the straps. It was really awkward. Emily then walked back into the room and laughed. "Need help?"

I turned around and she came towards me and hooked the bra. I looked down and the bra was tight across my chest, but the top of it hung away from my chest. My sister entered the room as I turned around.

She giggled. She opened a door in my dresser and threw some socks to me. "Put these in the bra." I did as she said.

She walked towards me and adjusted the socks in the bra. She then turned around and held up the dress. "Step into this," she said as she took it off the hanger. I did as she said. When I put my arms into the dress I turned around and she zipped up the back. The cotton felt cool against my skin.

"I don't think we need to shave his legs. His hair is pretty light," Emily said. My sister looked down.

"You're right. Must be all the tanning he does by the pool."

"Good. We wouldn't get to the mall if we had to shave his legs," my sister replied.

"I wouldn't let you shave them anyways! I have a camping trip this week. I'd be the only guy there with shaved legs!"

Suzy and Emily then left my room as I sat down on my bed to put the sandals on. I stood up and walked into the bathroom. I looked into the mirror. It looked like I had breasts underneath the dress! I turned and looked into my sister's room.

Suzy and Emily were both wearing jean skirts from my sister's closet with t-shirts. I stood in the doorway and looked at them. Suzy saw me and lifted her skirt up to show me that she wasn't wearing panties. I nodded and smiled.

"We have to do something with his hair," Emily said.

"Just a sec," my sister said as she left her room and I saw her enter my parent's room. She returned with a blonde wig. "Come sit down here," she motioned me to her makeup table. I moved and sat down.

She put the wig on my head and adjusted it. She did something and said that it would prevent it from coming off, if I didn't jerk my head around too much. I looked into the mirror. I had shoulder length dirty blonde hair! Emily then grabbed my chin and made me look at her.

She put blush and other make up on me. When I looked into the mirror, I almost didn't recognize myself. I looked like my cousin.

"We're gonna have to start calling you Stacy," my sister said. "You look like her twin, almost!"

"Yeah, I look HOT!" I exclaimed. Emily giggled.

I stood up and went downstairs. I heard the girls giggling as they finished getting dressed and then they clomped down the stairs. My sister picked up her car keys and said, "OK, let's go... Stacy." We walked through the kitchen and into the garage.

We climbed into my sister's mustang convertible. Emily climbed into the back seat and told me to get in the passenger seat. I thought his odd, but I wasn't going to argue.

My sister started the car and we left for the mall.

As we walked into the mall, the girls started talking about which store they should show me off in... We walked into the food court and a couple of other girls came up to my sister saying hi. My sister obviously knew them, but I had no idea who they were


My sister introduced me as her cousin, Stacy. A few of them just kind of looked at me strangely, but didn't say anything. I just said, "Hi," in my most feminine voice. After a few minutes of standing there and chatting, my sister and Emily led me away. As we continued walking through the mall, I got the feeling that my sister knew exactly where we were going.

We stopped in front of a store and my sister turned to me. I looked up and we were standing in front of Victoria Secret. I felt nervous throughout my entire body. "OK, here's what we want you to do. We want you to go in and ask the saleslady to help you find a new set of panties. Preferably a thong, but that's not necessary."

"No way. That wasn't part of the deal," I replied.

"I dare you too!" said Emily.

My sister got real close to me and whispered, "If you do this, I'll do *anything* you want me too."

I stood there for a few minutes, getting my courage up. Emily and Suzy stood there looking at me anxiously. Slowly, I began walking into the store. I walked into the perfume and lotion section and began acting like I was browsing. Emily and Suzy followed close behind me.

I picked up some of the lotions and smelled them, like I was really browsing. I could feel my legs shaking. I slowly worked my way through the doorway into the lingerie section. Emily and Suzy followed me giggling to each other.

I fingered some silk nightgowns and other items and then worked my way to the back of the store, where the panties and bras were kept.

As I started looking at the table that had all the thongs on them, a salesperson came up behind me and asked, "Can I help you find anything?" I turned and looked and it was Sharon!

Sharon was my next door neighbor. She used to babysit my sister and I when we were little kids. She was also a mentor to my sister in

cheerleading and is the one person both my sister and I can both say got us to start exercising regularly.

I looked at her to see if there was any form of recognition. Finally I said, "Um, yeah. I'm looking for a thong. This is my first time buying panties for myself."

A strange expression crossed her face and then she said, "That's fine. We get a lot of that here. What size are you?"

I didn't know how to answer that and I looked around for my sister and Emily. I didn't see them. "I don't know. My mom usually buys my undergarments."

Sharon smiled. "Well, why don't we go over here and find out." She took my hand and led me over to the dressing rooms. She took a key off her wrist and unlocked on of the doors. She held the door open for me and I walked in. I was felling very nervous. As I walked in, I noticed Suzy's face smile as she winked at me.

Sharon quickly walked into the dressing room, shutting the door behind her. She whispered, "I'm not supposed to be in here with you, but we'll be quick about this." She instructed me to turn around and face the wall. I did.

She then pulled out a cloth measuring tape from a pocket. She reached up underneath the dress I was wearing. "My, what hairy legs you have!" she whispered. I was nervous, so I didn't respond. She continued moving up my leg.

Suddenly, she stood up and lifted the dress above my waist. Her mouth moved and started nibbling on my ear. "Tom, I've wanted to do this since you turned thirteen..." Her hand moved to the front of the panties I was wearing and ran across my semi-erect cock.

"Oh, yeah! That's what I'm looking for!" she said. As she turned me around, she started pulling the panties down. She bent down and told me to step out of my panties.

As I stepped out of them, she took my cock into her mouth and started rolling it around her tongue. I felt myself growing while she licked.

As her tongue and lips moved across my cock, I felt the chaffed or bruised sections. They didn't hurt nearly as much as earlier in the shower. I leaned back against the wall and enjoyed the feeling.

I looked up and could see myself in the mirror that was along the wall of the dressing room. Sharon's head was bobbing up and down on my cock. Occasionally she would suck one of my testicles into her mouth.

She then stood up and dropped her pants and panties to her ankles. She turned around and put her hands on the bench that was in a corner. Without saying a word, I knew what she wanted. I moved behind her, bumping her since the room was so small.

I put my hand on my cock and positioned it at her pussy opening. "Not there. I'm not on the pill and you don't have protection."

I repositioned my cock at her asshole. I put the head of my cock in and Sharon moved back. It was tough sliding my cock in, but we hadn't lubricated her asshole. Sharon let out a soft moan. Suddenly, I was buried to the hilt. My hand reached under her and started fingering her cunt. Sharon started moving back and forth. I just stood there and fingered her pussy.

She started moving faster and faster. My dick started hurting and I grunted trying to prevent myself from screaming in pain. I suddenly felt the beginnings of an orgasm building in my balls. I closed my eyes and bit my tongue.

Sharon started moaning louder and louder. She moved faster and faster. I couldn't hold back. I released my load into her ass. I kept moving my fingers in and out of her dripping pussy.

Sharon's ass muscles clamped down on my dick as she let out a moan that she tried to muffle with her arm. I looked up at the ceiling and opened my eyes. I was looking right into the light. It seemed bright.

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