Comforting Pete

I looked down and he was hard already. We had been friends for more than 10 years, but we had never seen each other naked. Check off another thing in his column, he was bigger than me. Not just bigger, he was huge. How could so many girls leave him when he had this huge cock in between his legs?

"Are you just gonna stare at it or are you going to get me off?" He asked.

I reached my hand underwater and grabbed his hard dick. I couldn't believe I was touching another man's cock. Not just another man, my best friend. I stroked him slowly and he closed his eyes. I tried to copy what I did when I was jerking off, but who was I kidding, I pumped as fast as I could.

He started to moan, "Oh Jess, oh Jess."

At least he was pretending I was Jessica. I kept stroking him back and forth. It felt weird to be doing this underwater, but it felt weird to be doing it in general. I was starting to get into it and that was a problem, because I was getting hard. I panicked. I didn't want him to think I was enjoying this. I didn't want him to keep pushing me into doing these things for him. If he knew I liked it, he wasn't going to stop.

I felt his dick get even harder and from a lifetime of experience I knew what was about to happen. At least he was going to blow his load underwater and it wasn't going to get on me.

He moaned even louder and yelled, "Yes, Yes, Yes!"

I felt him throb and I looked down to see him ejaculating into the water. I moved back just in case, but the white fluid spread out under the water.

"That was great," he said, "Thank you."

"Well you didn't give me much choice," I said.

"Then don't lose bets!" He said, laughing.

"I'm kinda tired," I said, "Are you ready to get out?"

"Yeah, why don't you take a shower in the guest room and I'll lay out your sleeping outfit," he said.

"You really expect me to sleep with you?" I asked.

"That was the deal," he said, "And I meant it when I said sleep. Not sex...unless you want to."

"Let's start with sleep," I said. "I mean, just sleep, this one time."

"Whatever you say Jessica, I mean John," he said sarcastically.

I walked into the guest bedroom and looked in the mirror at myself in the red bikini one more time before I took it off. I decided to take a long shower and prolong whatever Pete had planned for me tonight. I took at him at his word that we would just be sleeping. I got out of the shower and dried off. Walking back into the bedroom I noticed the bikini and the clothes I had worn earlier were gone. I was shocked to see what was waiting for me on the bed. It was a tiny pink satin babydoll with black trim. Next to it was a matching thong and a bottle of Gucci perfume.

I pulled the thong up my legs. It was really no different that putting on a pair of underwear or the bikini bottom until the back strap settled between by cheeks and pressed up against my asshole. I jumped at the feeling and tried to calm down my hardening dick. I pulled the babydoll over my head and it barely covered my ass cheeks. I sprayed myself with the perfume. Wow did I smell girly! My dick was rock hard now and I started to hyperventilate. My thoughts turned back to what I was thinking in the pool. I couldn't let him know that I was enjoying this. Luckily the nightie covered me enough in front that I was able to put my dick against my stomach and hold it into place with the waist band of the thong.

I walked into Pete's room and he was already in bed waiting for me. He was shirtless and only wearing a pair of boxers.

"Wow Jessica, you look even better in babydoll than you do in your bikini!" He said.

"What's with the Jessica stuff?" I asked.

"I think we'd both rather pretend you're Jessica," he said.

"Ok," I said, giving in.

"Now why don't you climb in cutie," he said.

I gave him a look and got into bed with him. It was a king size bed, and my hope was it was big enough that he wouldn't have to touch me. Maybe the smell of her perfume would be enough to get me through this night and we could go back to normal tomorrow. We were both tired and he turned off the lights. I was a side sleeper so I rolled over with my head facing the wall.

SUNDAY

It turns out my chosen sleep position was a mistake as I woke up to Pete spooning me. His arm was draped around me and even worse his morning wood was pressed up against me. I tried to squirm and break free of his embrace, but that must have sparked something in him. He was snoring lightly so I knew he was still asleep, but I wished his hips knew that, because they started to move. His dick was pressing in between my cheeks with only the tiny material of my thong as a barrier. I squirmed more to try to get out, but he must have thought it was me thrusting back at him, because he started to move faster.

I heard him moan, "Oh Jess, Oh Jess," just like he had done in the pool. I heard him take a big gasp and I knew he was waking up. I felt something wet against my cheeks and he finally rolled onto his back.

"Oh My God, Dude, you came on my ass!" I screamed.

"Oh shit, sorry," he said, "I was having the most amazing dream about Jessica."

"Yeah, but she's gone, and your cum is all over me!" I said, freaking out.

"What's the big deal?" He asked.

"The big deal?!" I screamed. "We're best friends and we both like women. Your semen should not be anywhere near me."

"Ok, calm down, we were just having some fun and you were helping me out," he said.

"I think my debt has been paid," I said, "Can I take off this ridiculous outfit and wash up now?"

"Yes," he said, "Ill get your clothes out of the dryer and leave them on your bed. Sorry if you got upset."

"That's ok," I said.

I got up and walked into the guestroom. I stripped off the babydoll and thong and hopped in the shower. I washed up and scrubbed my ass so hard as if that would somehow make it cleaner from his cumshot. I got out of the bathroom and my clothes were on the bed, washed as he promised. I put on my button down shirt, pants and shoes.

Pete was waiting for me in the kitchen wearing his bathrobe. He asked me if I wanted to stay for breakfast, but I was anxious to get out of there. We gave each other a bro-hug and said we would call each other later. Walking to my car I reached for my keys. My pants had felt weird when I put them on, but I really wanted to get home so I just ignored it. Trying to find my car keys I touched something lacy in my pocket. I pulled it out and in my hand was a black thong. I shoved it back in my pocket before any strangers could see. I reached into my other pocket and felt more lace. I didn't dare pull whatever that was out and got in the car. Needing to know what was in there I pulled it out to reveal a bra. Pete had put one of Jessica's bra and panties set in my pants pockets apparently for me to take home.

I walked into my apartment and I was still exhausted. I stripped down to my boxers and took a nap. I woke up to the sight of black lace. It dawned on me that this is the first time I had lingerie in my bed. In my one and only time, we did it under the covers and she kept her shirt on. I didn't get to see her bra or her panties. My only sexual experience lasted two minutes and I didn't even get to see her naked. Then the last twelve hours popped in my head and I realized I just had double the amount of sexual experiences with Pete.

My mind was spinning and thoughts started to creep into my mind. Is this something I want to explore? Could I be a girl for him? I knew I still liked chicks, but my opportunities were severely lacking. I was staring at the bra and panties and remembered that in all the craziness, he had cum twice, but I hadn't cum at all. I had a crazy idea to jerk off while wearing Jessica's lingerie. I pulled up her thong, the second time I had worn one today, and it felt kinda nice. It took me a second to figure out the bra, but I was able to get it into place. I looked in the mirror and thought that if I had the rack Jessica did, I would have looked hot.

I was startled when I heard my phone ding. It was a text from Pete.

"Hey Bud, just checking in on you," he typed.

"Hey," I replied, "All good."

"Good to hear," he typed, "I left you a surprise in your pockets, in case you were interested in some more fun."

I started to type: "Yeah, I'm wearing them now." I quickly deleted that, not wanting to tell him. Instead I lied and texted back, "Ok, I'll check it out. I just woke up from a nap."

He didn't respond again so I went about my business. I got back in bed and began to rub my nipple through the bra. My dick sprang into an instant erection. I pulled it out of the thong and was stroking it while I continued to rub my hardening nipple. It didn't take long and I exploded all over my stomach. I cleaned up and threw the bra and panties into my hamper. My emotions were all over the place. First I was disgusted with myself for what I had done with Pete and just done to myself, but I also thought I could get used to it. I spent the rest of the day at home watching TV and catching up with some things on the computer. I had to be up for work so I went to sleep early.

MONDAY

I am always a good sleeper but last night I was all over the place, constantly waking up. I rarely dream, but when I do they're always wild. Tonight was no different as I had multiple sex dreams. The first one was me having sex with a girl. I couldn't make out her face, but she was into it. After getting up to pee I fell back asleep hoping that dream would continue. The second dream was the opposite. This time I was the girl and I was being fucked by a faceless guy. I must have been enjoying it because I woke up to my hips thrusting against my mattress and I had cum all over my boxers. I hadn't had a wet dream since I was a teenager. What the hell was going on with me?

I got up and took a shower to clear my mind. I went to work and had a pretty uneventful time. I hadn't thought about Pete or sex the entire day. That changed when I got home and there was a shopping bag hanging on my doorknob. I looked down and saw colors staring back at me. I quickly brought it inside before any of my neighbors could see. I opened the bag and saw the Red Bikini and the Pink Babydoll and Thong that I had worn at Pete's over the weekend.

There was a note that said: "J, since you wore these so well over the weekend and Jessica isn't coming back for them, I thought you'd like to keep them. P."

What the hell? I thought to myself. Why was he giving me her clothes? I now had three sets of them. When he texted me a "Hey" later that night I ignored him. I did what I usually did on a work night, ate dinner and watched TV. I kept the outfits in the shopping bag and tried not to think about them.

TUESDAY

I had a better night's sleep followed by the same boring day of work. When I got home there was another bag waiting for me. This time it was a Purple Bra and Panties set with a Garter Belt and Purple Stockings.

The note said: "J, just a few more things for your collection. Hope you enjoy! P."

My collection? This was getting a little out of control now. I put the bag next to yesterdays and made myself dinner. I tried not to think about what was inside them, but I couldn't stop staring at the bags. After eating I sat on the couch and opened the bags. I pulled out the Bikini and Babydoll and my mind flashed back to what happened when I was wearing them. I pulled out the Purple set and was drawn to how silky smooth the stockings felt.

My dick started to tingle a little bit and I figured nobody would know if I tried it on and played with myself. I quickly stripped down and put the lingerie on. The familiar feeling of the thong strap against my asshole felt great and I was a pro at putting on a bra by now. I pulled the stockings over my almost hairless legs which gave me a huge boner. I clipped the garter belt around my waist and attached the straps to complete the look. I checked myself out in the mirror and I thought I looked pretty good. I sat back down on the couch and started to jerk off. I tried to think of those sex dreams and realized that any girl would be laughing at me if she saw me dressed like this. Instead I pictured myself as a girl getting fucked. My body started to tingle and I had a huge orgasm, cumming all over my new lingerie. Feeling a little ashamed I stripped everything off and threw it in my hamper. I realized that I would have to figure out how to wash all of this lingerie, but that was a problem for another day.

WEDNESDAY

I had a good sleep and another normal day of work. On my way home my mind started to wander and I was excited to see what he had left me when I got home. To my disappointment there was nothing there. I changed out of my work clothes and couldn't stop wondering why he hadn't brought me anything today. I let it go and went on with my evening.

THURSDAY

I woke up on Thursday morning and got ready for work. All day I was thinking about Pete and if he was going to bring me something tonight. It was strange that he had given me something on Sunday, Monday, and Tuesday and then just skipped yesterday. I kept looking at the clock while I was driving home, hoping there was something at my door. For the second day in a row there was nothing. I had to admit I was enjoying Jessica's lingerie, but I didn't want to admit to myself that I wanted to wear it in front of Pete while we fooled around.

I couldn't stop thinking about things and I broke down and texted him: "Hey, Dude."

It took a little while for him to reply, and he wrote, "Hey Bud, what's up?"

"Not much," I wrote, "Just checking in."

"Oh, I thought you might have something you wanted to ask me," he wrote.

He knew exactly what I wanted, but I didn't want to give him the satisfaction. "Like what?" I asked. "I haven't really talked to you in a couple days and I didn't know if you were going to be in the neighborhood again."

My phone rang. It was Pete. I answered and before I could say hello he said, "Sounds like you've been missing your surprises."

I froze and all I could say was "I..."

"You didn't say thank you, so I didn't think you liked them," he said.

Finding the words, I said, "I didn't expect you to be bringing me that stuff."

"But now that I skipped two days, you're upset," he said.

"No, I mean, I..." I started to say and froze again.

"I knew you'd like everything. Tell me, did you try anything on?" He asked.

I couldn't resist anymore I said, "Just her Black Bra and Panties and the Purple Lingerie set with the Garters."

"Is that all?" He said, laughing. "And they're not hers anymore, they're yours."

"Whatever you say," I said.

"Did you play with yourself while wearing them?" He asked.

"Uh...yeah," I said.

"Were you thinking about me?" He asked.

"Ew Dude, No," I said, not wanting to admit I pictured myself as a girl getting fucked.

"Then I guess I have more work to do," he said quietly.

"What was that?" I asked.

"Nothing," he said, "If you want me to bring you something tomorrow, all you have to do is ask."

"I don't know Dude," I said, "Isn't this kind of weird?"

"If you're enjoying yourself, how can it be weird? I'm happy to bring you more things, but when I give someone a gift, I expect to be thanked for it," he said.

"Ok," I said, "Talk to you later."

I hung up and felt embarrassed. I can't believe I admitted to jerking off while wearing lingerie he gave me. Did I really want to do some more things with him? It sure beats doing stuff alone. I haven't even attempted to pick up my own girl in forever. Maybe it will feel good? I guess it couldn't hurt to try, he is my best friend. We could always chalk it up as a joke. I'd definitely have to think more about this.

I walked over to my hamper and took out the worn lingerie. I noticed it had a perfume smell to it. He must have sprayed it before he brought it over and in my excitement I hadn't noticed. I washed the dirty items in the sink and let them dry. I made some room in one of my drawers and put everything away. I had two Bras, three Thongs, a Babydoll, a Garter Belt, a pair of Stockings, and a Bikini. I had quite a collection so far and knew I wanted more.

I picked up my phone and texted him, "Thanks Dude for giving me those things earlier in the week, if there's anything else you'd think I'd like, I'd appreciate it."

He just replied, "Ok."

FRIDAY

Friday was another light work day and the boss let everyone home early as usual. I was anxious to see what, if anything, was waiting for me at my front door. I sped out of work and rushed home. My face lit up when I saw a bag hanging from my doorknob. The bag was heavier than usual. I walked into my bedroom and stripped down naked. My cock hardened in anticipation and I wasn't disappointed. A flash of pink hit my mattress as I turned over the bag. He had given me a Hot Pink Bustier, G-String, Garter Belt and Stockings. Then out came a Short Black Tight Dress. Lastly there was a yellow bikini. He had really gone all out.

The note said, "J, a little something for you to enjoy tonight and I was thinking you could join me tomorrow for some swimming and barbecue. P."

I picked up the Bustier and wrapped it around my midsection. I tried to hook it behind my back but there was no way. Then I remembered I've seen girls hook it in front and spin it around. It was tight, but it had a little give to it and I knew I would get used to it. I pulled up the G-String and laughed when my boner was sticking straight out. The tiny string settled against my hole and I got a chill from that familiar feeling. I attached the Garter Belt and Stockings. I pulled the Black Dress over my head and smoothed it down my body. I was never a tank top or sleeveless shirt kind of guy, so it was a new feeling to have the straps of a dress over my exposed shoulders. I looked in the mirror and other than my lack of tits and huge hardon, I looked great. I decided I would spend the rest of the night wearing this, but first I needed to take care of myself. I pulled up my dress and jerked off into my bathroom sink. After that my dick calmed down and I was able to settle it into my panties. I brushed my dress back down and now I had a smooth front.

The rest of the night was uneventful. I had a little trouble moving around with the bustier on, but I was able to make dinner with no problem. It was when I sat down on the couch with my Little Black Dress barely covering my ass and my legs in the Pink Stockings that I knew I wanted to explore with Pete. I was getting hard again and pulled off my dress. I was going to masturbate while I was wearing my pink lingerie. I walked over to my full length mirror and started stroking. I closed my eyes for and pictured Pete behind me. I imagined his hand was the one that was giving me a hand job. I was rubbing and tugging really fast and I came all over my mirror. I opened my eyes and giggled to myself. Was I really wearing Pete's ex girlfriend's underwear while I just pretended he jerked me off? My life has certainly taken a turn from a week ago.

I felt sexy and thought I could sleep in this outfit. I got into bed and it was a bad idea. The bustier was too tight and there was no way I could sleep like this. I took it off and opened my drawer to put it away. My Pink Babydoll caught my eye and I figured that was close enough to match what I already had on. I laughed to myself again, because I had no idea why I was worried about matching outfits, it's like my brain has totally changed already.

SATURDAY

I had a good nights sleep and I really loved the feeling of the Garters tugging on my Stockings every time I moved. I woke up to a text from Pete that said to come over whenever I wanted to. I got out of bed and into the shower. I knew he expected me to wear the bikini in the pool, so I decided to shave my entire body. As I mentioned earlier, I didn't have much body hair, and he probably wouldn't have noticed either way. I wanted to do this for me.