She knows best.
My girlfriend Kelly invited me to spend two weeks with her family at their lakeside house. It was 5 hours away so when her Dad suggested I just go up with them I said yes. Kelly got mad at me.
"Great now we can spend 5 hours listening to old music crammed in the back of my parents van" she told me. I tried to tell her I go back and tell her dad thwt I would drive up.
"Forget it, he will know i talked you into it" she told me. Now her Dad's van was huge it had bucket seats in the back. A tv. We where going up in luxury. And it was only her sister Jan. That would be back there with us.
The night before we where to leave we where watching Jan and the boy from next door shooting hoops in their driveway. Jan was winning and she went to make her last shot the boy ran up and pulled down her shorts. I laughed. And Kelly hit me. As Jan just pulled up her shorts. Telling the boy off, she had made the shot.
"So what its funny to see a girl humiliated by having her underwear exposed" Kelly was chewing me out. Great now one more thing for her to be pissed about this whole trip. I tried to apologize pointing out that Jan didnt even care.
"Well let's see how you care" she went to the back of the already packed van and opened her suitcase. She pulled out a pair of her panties.
"You will wear these all day tomorrow, let's hope no one notices" she told me.
"Kelly I'm not going to wear" I started.
"You will or we are done, understand" she was serious. I stormed off home. Having shoved her panties in my pocket. I stewed about this for hours then fell asleep. I woke to my alarm it was 5 am. They would be here in 30 minutes to pick me up. I had thrown Kelly's panties on my desk. I showered and now was staring at them. I slid them on. They where white bikini cut panties. I was surprised how comfortable they where. I threw on my jeans and a sweatshirt. I grabbed my stuff. Just as Kelly burst thru the front door. She grabbed the front of my jeans.
"Good boy" she smiled and helped me with my bags. "I will have to think of a special reward when we are alone" she told me.
Kelly was in a great mood, but when stopped for lunch she hugged my arm. "You should get the grilled chicken salad, healthier" she smiled. Not wanting to upset her again I did as she said. And watched as she ate a greasy burger and fries. We had a few minutes while her parents finished up. She walked me around to the other side of the building.
"How do my panties feel" she smiled.
"They are much more comfortable then I would of thought" I confided in her. She smiled and pulled close kissing me her hands grabbing my abs.
"I am glad to hear that, I would love it if you wore my undies the whole trip" she cooed.
"Kelly, I can't" I pleaded.
"Sure you can, promise me" Kelly smiled and nibbled on my ear.
"Okay" I told her. She kissed me and flashed me her tits as she headed back to the van. I followed after her. She cuddled up to me in the back of the van. As her parents and sister piled in. Jan made a face when she looked at us. Kelly kissed me and stuck her tounge out at Jan.
We finally arrived i was just happy to get out of the van. I helped her dad grab the luggage. As I came out to grab more bags. I saw Kelly over in front of the neighbors talking to some guy.
"That's Damon" Jan told me walking up behind me. "Kelly and him had a kind of thing last summer" she giggled.
"Let's go Paul" Her dad said patting my shoulder. I went and grabbed 2 more bags and headed in. Kelly was still next door after I had bought in all the bags. I walked over.
"This is Paul" Kelly said hugging my arm. "Paul this is Damon" she introduced us. We shook heads. Damon's grip was like a vise. Kelly led me back to the house.
"We are going to dinner" Jan told us as we walked in.
"You need a shower" Kelly told me. "I will pick you out something to wear." I rushed thru the shower and found a pile of clothes Kelly had laid out for me. On top was a red thong. I couldn't wear this is thought. But Kellys mom knocked on the door "5 minutes" she called out. I quickly slid on the thong and got dressed. I came downstairs and went to put my wallet in my pocket when I realized the pants had no pockets. Kelly took my wallet and put it in her purse without a word. As we got out of the van at the restaurant.
"You look good in my pants" Jan whispered in my ear. "And Kelly's" she hugged on the back of the thong lightly. I tucked the shirt in. Blushing beet red.
"Kelly I'm wearing Jans pants?" I said nervously
"You didn't have anything nice to wear" she shot back. As we waited to be seated. Damon and his family came in. The families where old friends. Kelly was talking to Damon. I stood against the wall trying not to be noticed. Kelly was laughing and gently touching Damon's arm. When we went to be seated he slid Kelly in front of him and held her waist all the way to the table only when he went to sit at his own table did Kelly even remember I was there.
"Prehaps the grilled chicken" Kelly suggested quietly as I went to lift the menu. I just nodded and put the menu down. Everyone ordered steak. When it was my turn to order Kelly ordered the grilled chicken for me. I felt like a child having his mother order his food. But I said nothing. I sat quietly as everyone talked about what had changed or upcoming events at the lake this summer.
"There is a get together tonight on the beach" Kelly started to tell her Dad.
"Alright" he nodded. "But be home. In the house by midnight" he warned her. "Got that Paul!" He shot a look at me.
"Yes sir midnight" I said sitting up straight.
"Can I go?" Jan asked.
"Paul can you keep an eye on both of them?" Her dad asked me.
"Yes sir" I responded before I looked at Kelly. She wasn't happy I had agreed to take her sister along. But Jan was happy.
"I can't believe you agreed to babysit" Kelly snapped at me when we where back at the house.
"I didn't mean, I just wanted to" i dropped my head. "I'm sorry"
"You will be, she is you're problem not mine" Kelly told me.
"Kelly it will be fine, she isn't a monster or anything" I tried to get her to see Jan would be okay. She pulled a pair of white panties with a wide lace waist band. "Let's get you dressed for the party" she smiled. She tossed the panties at me. As I held them she started to undress. I followed suit. Her parents where just downstairs, her sister in the next room. She was named and bending over looking thru her bag. I wanted her I still stood there in her red thong. My dick hard. I pulled the panties down and stroked my dick.
"What are you doing" she said sharply. "Do you cheat on me like this alot?" She asked.
"You mean Jerk off? Yeah" I confessed.
"Well that's cheating in my book" she told me.
"Kelly it sorry I mean everyone" I started then looked at her face. I just turned and slid off the thong and put on the white panties.
"Those look so cute" Kelly mood changed when she saw me put them on. "Now these are for letting Jan come along" she handed me a pair of denim shorts. They where low riders. The lace of the panties on full display. She one of her tee shirts it was very tight and wasn't long enough to tuck in. Kelly wore shorts coming down to her mid thigh and an oversized tee shirt.
"Kell I can't" i started
"Then stay here, with mom and dad" she told me. Just then Jan burst in.
"Dad is never letting you out of the house wearing them" Kelly told Jan who had on pink booty shorts. She grabbed Kelly skirt and pulled it on over them. Kelly just nodded. The they both looked at me. And laughed. Kelly ran to my room and returned with my big hoodie i pulled it on.
"Perfect" Kelly smiled. I followed the girls downstairs.
"Paul!" He Dad called from the kitchen.
"Midnight sir not a minute later" I replied and we headed out. Once we got to the beach
"Keep an eye on my sister, or tomorrow you will be in a dress" Kelly told me then disappeared into a crowd of people. Jan headed towards the other end of the beach. I followed after. I didn't see Kelly for hours. But was having fun hanging out with Jan. When Jan said she was cold I didn't even think about it and took off my hoodie. As soon as I did a guy asked me to dance.
"No" I shot back at him walking away. Jan followed after me.
"Sorry want your hoodie back?" She asked if shook my head no,
"We need to find Kelly, it's almost midnight. I told her.
"I will check on the beach, check up by the boat house" she told me pointing. I didn't want to leave Jan but there were so many people around I figured she be fine. I got up to the boat house and saw Kelly with Damon. They were naked. I could see from the small light at the corner of the building. I hid behind a tree and watched. As Damon had her in his arms against the building. I could here her coos and his grunts as he drove his cock in and out of her. There bodies glistening with sweat. I was so turned on I pulled out my dick and perked off as I watched. I came quickly. But Damon kept fucking her I played with my soft dick as I continued to watch. Jan came to behind me.
"Jesus" I swore. She just put her finger to my lip. "It's so tiny" she teased i went to put it away.
"No wait" she looked to see what I had been watching. Jan watched as I tried to get hard again. When we heard Damon grunt loudly and then pullout putting Kelly down. She raised up on on tiptoes and gave Damon a little peck of a kiss. Damon just grabbed his clothes and left her standing there. She was looking around for her clothes. Jan pushed me out of the shadows. I quickly pulled up the shorts.
"Paulie where you watching?" Kelly giggled. She wrapped her arms around my neck. "You where touching yourself while you watched." She continued to tease me. "So we had sex together" she laughed. Still naked.
"We have to go!" Jan yelled from the bushes. I looked around and found Kelly's shorts. She slid her phantom between her legs and wiped it on my shirt before she pulled her shorts on. She hadn't even tried to find her underwear. Jan came out and handed her my sweatshirt. That's when Kelly realized I had been walking around with my panties showing. Kelly adjusted my waistband.
"Paulie was a hit with some of the guys on the beach" Jan told her laughing.
"I think he was much more interested in watching me and Damon" Kelly told her. Smacking my ass as we stepped on the porch. I checked my watch we just made it. Kelly rushed me upstairs. Kelly pushed me into my room and closed the door behind us.
"You liked watching me with him didn't you?" Kelly wispered giving my ear a little nibble. Her hands cupped my ass. "I want to keep fucking him. I want you to want me to" she told me.
"He has a
very big cock, it makes me feel amazing. Your little penis likes my panties" she continued. "You can still please me with your tounge, like if we where lesbians" Kelly unbuttoned my little shorts and rubbe the front of my panties.
"You went out today dressed like a little slutty girl" she reminded me. "Maybe you don't want to be a lesbian, maybe you liked watching Damon's thick cock" she teased.
"No" I whimpered.
"Do you want to kiss me, I had his cock in my mouth tonight" she told me and kissed me. Her tounge danced in my mouth.
"No I want you" I told her after she broke the kiss. She smiled and opened her shorts. "Then kiss me" she commanded. Pushing me down to my knees. I knew he had finished in her less then 15 minutes ago. But I leaned forward and kissed her.
"That's what I thought" she told me. Zipped up her shorts and left me on my knees as she snuck back to her room.
I went to bed, I couldn't leave how would I get home? Why did it excite me so much to wear Kelly's panties. Not just her panties! I thought about watching Damon fucking Kelly. I wanted to Jersey off again. I couldn't Kelly would know. At some point I fell asleep.
Kelly woke me in the morning.
"Damon is taking us out on a boat today" Kelly told me putting a yellow bikini on my chest. She kissed me and ran off. I got showered and put on the bikini. It had ties on the sides. I didn't need the top biput put it on anyway. I threw on a pair of my shorts and a tee shirt over it and went down to breakfast. Kelly's mom stared at me closely then quietly asked Jan something. Jan just nodded yes. Kelly's mom just smiled and offered me a plate. Kelly came down and just had tea before we set off. Jan joined us.
"She your babysitter" Kelly told me. "If Damon wants to have sex today, I want you to play with yourself, so it's like he is having see with both of us" Kelly told me. "Your other job is to make sure no one takes advantage of this one" she laughed grabbing Jan playfully.
WWe met Damon and anther guy Harry at the dock. As soon as we where on the boat the girls took off there clothes so they where in bikinis. "It's okay Paulie" kelly told me pulling my shirt off. When the guys didn't laugh or tease I removed my shorts as well. Kelly rubbed sunblock all over me. But Damon rubbed it all over her. I looked over to see Harry rubbing lotion on Jan. I looked back at Kelly and she yanked down Damon's swim trunks. She showed me his encouraged cock. She then knelt and took it in her mouth. I watched my dick hard in my yellow bikini.
"PAULIE!" Jan cried out panicky. I rushed over to see Jan had her hand wrapped around Harry's cock. "Paulie I cant" she said looking at me. I just led her away. Harry didn't move.
"I freaked i cant finish, men can have issues if they don't finish" she told me.
"It's okay Jan, he will be fine" I assured her
"No, real men with full balls need to finish" she told me. "Please help me finish him" I looked over to see Kelly sucking Damon's big cock down her throat. "I was just using my hand" Jan tried to explain. I nodded and went and sat where Jan had been. I didn't even look at Harry I just grabbed his cock and started to give him a hand job.
"Kiss it show it some love" Harry told me. I looked up at him. His eyes soft. I knelt and kissed the tip of his cock then sat back up. His hand slid under my bikini top and he teased my ripple. I looked up at him again he smiled. I knelt and kissed his cock again. This time I put the head in my mouth and tasted his precum. Then he grabbed my arm as his cock exploded covering my hand and wrist in his seman. Harry pulled up his swim trunks and went back to consoling the boat. I rinsed off my hand in the lake and sat next to Jan.
"I never did anything with a guy, thank you" she said and kissed my cheek. I looked around and realized Damon had taken Kelly down below. I went to find them as soon as I got down I saw Kelly coming on his cock. I played with myself as Damon finished. He pulled out and shot his load on her stomach. Damon got up and laughed as we walked past me. I just stared at Kelly laying there covered in cumin. And I came in my bikini.
"Come give me a kiss" Kelly said to me. I hesitated then knelt and kissed her pussy like I had last night. "Ummm you like that don't you" she cooed. Rubbing my head. She got up and dressed. We both jumped in the lake. We spent the rest of day sunbathing on the boat. On our walk home from the dock. Kelly grabbed my arm.
"Jan told me about Harry" she grinned. "Did you enjoy kissing his cock?" I was so flustered I almost tripped over my own feet. I didn't answer i was so drained from a day in the sun I fell asleep. Before dinner. I woke it was dark.
"Paul, can I" it was Jan. I went to turn on the light. "No don't. She laid on top of me. The blanket between us. "I have never been with anyone. And this was my summer to well. And I freaked." She was saying. "Kelly told me you are good with your tounge, and I trust you not to want more then that" Jan told me. She moved and squated on my face. "Please" she said as she rubbed her pussy in my face. I just started to lick and suck her. She pulled my hair. I had only ever been with Kelly and one other girl. But neither of them had ever reacted so. She even stuffed something in her mouth to stay quiet. As she came multiple times. She collapsed rolling off of me.
"Now I almost wish you weren't gay" she told me.
"I'm not" I told her.
"You wear woman's clothes, jerk off guys and watch your "girlfriend" get railed by someone else. At the rate you're going you will be getting it gangbanged before we leave" Jan told me "if I was you, I sneak into my sister's room and ue that tounge to remind her why she dated you for so long" Jan got up and left.
I laid there for a moment then got up and sneaked into Kelly's room. I didn't wake her just slid under the covers. And kissed her thighs she parted her legs. I kissed her thru her panties. Suddenly the blanket flipped back. "Paul" she said in hush tones. I pulled her panties off. She didn't stop me. "Gently im sore" she told me, but as soon as I buried my tounge in her everything was weird, "Don't stop" she pleaded pulling my head back between her legs.
"Damon just left" Kelly told me my face now covered in his seman. "No please it feels so nice" she said holding my head between her legs. "This is how it should be from now on., don't you agree?" She said rubbing my head gently.
"If you think so" I told her then went back to cleaning her used pussy.
