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So I’ve been having this dream pretty much every night for about 2 months, gradually becoming more vivid and remembering more of it when I wake up. Not sure if I should try to make it happen or ignore it. I’ve never really done anything like, so any input would be appreciated. TIA.

So, I’m a guy(49) and not really sure what to make of this dream, but it has really peaked my interest. The friend in the dream is someone I don’t know. I don’t recall ever meeting this person.

I’m hanging out at single friends place(don’t know who he is in the dream). We’re just sitting around watching TV and talking about everything. He gets to talking about his ex who just up and left and didn’t even take all her shit with her. I was like hell throw it away. He said he would, but he all the time liked it when she wore the stuff she left. I laughed” show me what she left”.

He brings out a bag full of thong panties, very small mini skirts, make up and a bottle of Nair lol. I told him “this stuff looked hot and I understood why he still had it”. He said “yeah but thing is he can’t find a girl the same size as her to wear the stuff. And that sucks. “. I agreed with him on that. He then looked at me” you’re kinda small, I bet you could wear it.”
“I think I’ll pass” I laughed
“Aw, come on man. It’s just some clothes and nobody’s gonna know. Before you say anything, no I’m gonna try anything. Hell I don’t think I could ever get hard over a guy anyway. ”

He actually seemed kinda sad, I know he really loved her. After basically begging me a few times I caved” fine I’ll put something on, but don’t get disappointed when I don’t look like you hope I will. ”
Really? You’ll do it? You’re awesome bro! Here wear this. ” As he picked a few things from the bag and handed it all to me. He included the Nair and makeup. “why this”I asked.
“Just in case you want to try is all, you don’t have to” he said sounding really down.
“You can use the bedroom, take your time, no hurry at all” he said
In bedroom I looked at what he handed me. A size xs black thong, thigh highs with garter and a tiny skirt. I wondered no way I’ll get most of this on, and didn’t really know where to begin anyway.
I figured I’d try the panties first. They were a little tight but I managed to get them and kinda stuff my dick into them. Oddly I got kinda tingly and really felt good with the thong on. I looked in the mirror and apparently decided to do a little clean because next thing I know I’m in the bathroom with Nair smeared all over my ass and thighs. I’ve never used the stuff so I don’t really know anything about it I’m guessing I got it off because suddenly I was putting the thong back on and feeling kinda strange. I then figured out how to put on the stockings and the garter which made me literally shiver because of the way it made me feel. I pulled on this tiny little skirt not sure exactly where to put the waist band but I got it on and it was tight. I have long hair that I’ve had for years so brushed my hair and ignored the makeup and walked out of the bedroom. My friend looked up from his phone and was shocked.
“Wow. You actually have pretty nice legs and your butt is kinda cute. ”
“Don’t get used to this, it’s coming off soon” I said. But I didn’t really want to take it all off just yet.
“Aw hell just leave it on for a few minutes, it ain’t gonna hurt nothing. Besides, the game’s on, so just sit down.”
I sat on the opposite end of the couch, not realizing I’d kinda pulled my legs up beside me like I see lots of girls sit.
“You’re into aren’t you? Don’t lie. It’s cool man. Our secret, I PROMISE. ”
“I don’t know. I mean it’s not like the stuff is uncomfortable or anything, it’s just weird I guess.”
I have never even considered dressing like that before, but I was kinda into it. Not sure how long we at watching the game but something happened and we were both up and cussing the refs I think and when we sat down I was a lot colder to him and had butterflies in my stomach. I kept thinking what the actual fuck is wrong with me today. A little later we were up cussing again and I stumbled because one of legs kinda gave out and he caught me before I could fall. I felt an electric type of feeling go through me but I dismissed it quickly. I went and grabbed another beer and feeling playful I guess, I kinda shook my ass at him. He just damn, I wondered he was talking about the game again. I was bringing him a beer and I didn’t see one of his shoes and I tripped. He caught me again but now we were face to face very close. He leaned up quickly and gave me a really quick peck on my lips. I was totally shocked, but before I could stop myself I leaned to him and gently kissed his lips. Then sat his beer on the table. Suddenly, he pulled me to him and our lips locked, instantly or tongues were tangled, one hand slid to my ass. OMG I was dying and nervous and didn’t know what to do. He pushed me away, apologizing like crazy.
“I’m so sorry I don’t know what came over me I’ve never ever been attracted to a guy, fuck man I’m sorry if you wanna leave I understand. ”

I sat back on the couch”I’m not mad, it was kinda nice I think. It happened so fast I’m not sure. I’ve never done anything like that before so I’m not sure how to feel about it.”
“You sure you’re not mad?
“Yes I’m sure.”
Sitting there I could only think about kissing him again, I must be going crazy, I’ve never even wondered of this before. WTF do I do.

Finally a commercial came on
“Can I ask you something?”I asked nervously
“Off course, anything. ”
” Ummm, would you want to do that again? Sorry I asked it’s cool just forget it I’m sorry” I was stammering
“Do you want to?” He asked
” Yeah kinda, you know just because last time happened really fast and I don’t know how I feel about it”
He just pulled me over to him and we started kissing we were both nervous we could feel that from each other. It was hard to relax but once we did, things escalated quickly. The kissing for really intense, at some point I ended straddling him as we were pulling each other tighter kissing hard. I could feel his dick begin to get hard as his hands were squeezing my ass and grinding me against him, my nervousness got worse but I couldn’t stop, I just couldn’t, it felt so good. His cock was raging hard and he broke our kiss. He looked in my eyes”do you want to try?” He asked, the look in his eyes was lust mixed with terror.
“I think we have to, or we both going to regret not trying. I’m scared, but I don’t want to stop”
“I’ve never even done anal with a woman. ”
“I’ve never done anything like this at all. We’ve got to. ”
Holding on to my ass with my arms around him our lips came together again as he stood up and lifted me with him.
I’m kinda small I guess about 5’7 130lbs he’s around 6′ strong athletic create. Tongues still fighting, he carried me to the bedroom and gently placed me on the bed while crawling on top of me.
With wild abandon I started trying to push his shorts down, he took over and removed them completely.
I reached between us and felt his swollen cock for the first time. I don’t know how big it was but it felt quite long and my hand wouldn’t close around it. I almost panicked at this point. I mean I’ve seen porn and seen guys fuck women in their ass and all the time wondered, that cannot feel good at all.
” How do we do this” he asked breathlessly.
“I don’t know. Maybe try lifting my legs up.”
He hooked my legs with his arms and lifted them. I reached for his cock but the angle still wasn’t working.
“Push them back more” I said still trying not to panic.
He gently pushed my legs back as my ass started to lift of the bed, his erect cock brushed against me” this might work”I said nervously.
“You need to take the panties off. ”
“I think I can pull them to the side. Besides I don’t want keep waiting or I’ll chicken out. ”
At this point I had no idea what the fuck I was doing. Neither one of us ever wondered about any type of lube at all. I pulled the thong out of the way and started to guide his cock to me. Not being able to see what I was doing, the head of his cock touched just below my hole, I moved it up and as soon as it touched my ass hole it sent chills through me. I could feel the slick precum oozing from his cock head as it pressed against me.
“Is that the spot?” He asked very anxiously.
“Yes. Just keep holding my legs back and see if you can get in. ”
He started trying to push into me, it wouldn’t go so he pulled back and pushed again.
“FUCK! STOP! AHHH FUCK THAT HURTS!!”I almost yelled when the head went in.
He immediately stopped leaving the head inside”I’m sorry. We’ll stop.”
“No. We have to try. Just go real slow.”
“Maybe if we kiss more you can relax again” as he lean down to kiss me.
It was awkward at first, then the fire started again. He started to push into again slowly.
It hurt like hell, but as he began to slowly work his cock in and out of me it started to feel good. I remember seeing cock on the night stand don’t remember the time, but he fucked me slow for what seemed like hours, the whole time we’re still kissing. He working his full length into me now and It felt amazing.
“Are you ok?” He asked
“It’s amazing, don’t stop. ”
He was fucking me with a steady rhythm by now.
Suddenly he pushed all the way into and stopped being our kiss”AHHH FUUUCCCKKKK!!!! I’M CUMMING!!!!!”He almost shouted.
As his cock started to go down is slid from inside me, he let my legs down and sat up on his knees.
“I’m so sorry, I didn’t mean to cum inside you. ”
“I don’t mind, I loved it actually. Besides, not like I can get pregnant. ”
We laughed and I woke up.

Any comments would be appreciated. Remember this was an actual dream that I keep having. I don’t know what I need to do. Should I try to make that happen or just try to forget about it.

NSFW: yes

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