Then I made my first mistake by mentioning my weekend away plans to my friend Jeff (less the cross dressing plans of course). Jeff is a good friend. He is currently COVID-19 laid off and wants out of the house as much as anyone else. He asked if he join me and would split all the costs and driving. There was no good reason to refuse my friend so I had to agree. I also needed to adjust my plans. I would have to take advantage of Jeff's love of beer to obtain some alone time. We agreed to take his SUV because it was bigger than mine and so he could go out and about if he got bored in the cabin.
It took a little effort to pack a bag with straight and fem clothes yet look like it was a guy's bag for a weekend but I managed. I packed my fem clothing in a very small bag and stuffed it in the bottom of my large pack back bag. I had no idea how this weekend was going to work but I had what I needed to dress even if for only one hour in my room.
The drive up on Friday was un-eventful and easy. I started my weekend by wearing purple bikini cut panties for the drive up. Casual conversation and light traffic. Checking in was even easier as it appeared there were only three or four other cabins being rented. We threw our bags in the cabin and picked bedrooms. Then we took off to explore the local eateries that were open. Main Street was a few miles away but it had everything we needed for the weekend. We picked up food, beverages and pizza menu's and headed back to the cabin. I quietly pushed Jeff to buy plenty of beer. I don't drink very much but it seemed like my best bet for the weekend was to keep Jeff buzzed and passed out.
The weather was good but we were not going swimming. It was going to be a sports shorts and blue jeans weekend. We ordered a pizza Friday night and enjoyed it by the lake edge. Little did Jeff know I was wearing purple panties under my board shorts. It was not the first time I wore panties outside the house but it was first time I did while sitting that close to another person. It was quite exciting.
We returned to cabin as the sun was setting and watched some TV. Jeff found one those Friday night wrestling programs and settled into the couch with his beer. I was still a little excited and started thinking about what to do for the first night. It was already getting late so I decided that I would just sleep in my panties and a T shirt. Wigs can be a lot of work and the bra is too tight for sleeping. All the while I was day dreaming and scheming Jeff watched his program and drank his beers.
After the show ended Jeff used the bathroom and announced he was going to sleep. And then, straight out of blue, he said that his girlfriend liked him to keep himself trimmed south of the border. You have to love the effects of beer LOL. I responded with it's a good idea to go sleep off the beer and that it's OK to keep neatly trimmed down there.
Then, out of blue, I stood up, dropped my shorts and slowly peeled down my purple panties and exposed my fully shaven crotch to him. It was a huge moment of truth for me and a major stunner for Jeff. He was absolutely speechless for a minute. I was scared that I just ruined our weekend and possibly a friendship. After he regained his thoughts, he tried to have the whole "are those panties, why are you wearing panties and are you gay" conversation but he was just to drunk. None of this was part of my weekend dressing plan but here we were. I pulled up my panties and turned around showing him how good my butt looks in panties (my butt is my only fem feature but at least it's small and round). I pulled my panties real tight and bent over slightly as I prepared myself for Jeff to announce that we were leaving. He was a little un-steady as he stood up so I moved in close to help him stand. He mumbled the "are you gay" thing and I told him that I occasionally dress for me and not to have sex with other guys. By this time, he had leaned into me for support and had his hands on my ass (whether he knew it or not).
We were basically wrapped around each other as I walked him towards his bedroom and got him down on the bed. He kept pulling at my panties all the while but I managed to keep them up and on. He was still drunk, still stunned and still unable to complete a sentence as I covered him with the blanket. My advice to him was to sleep it off and consider it a bad dream. As I was about the leave the room, I ran my hand over his crotch for a quick boner check. I think every cross-dresser wants to be responsible for a hard on. The results were inconclusive.
I left him mumbling, closed down the cabin lights and TV and retreated to my room. Panic set it quickly. It was not the plan to show my shaven crotch and panties to Jeff. The plan was to sneak in some dress up time. I laid down to sleep knowing there might be some issues in the morning.
Then, in the wee hours of the morning I was awakened by movement. Jeff was naked and rubbing his hard on against my panties covered ass. It took me a few moments to gain my senses from a dead sleep but here was my friend hot dogging me. I wasn't sure what to do so I just laid there until I felt Jeff pushing my panties aside. Then I felt his fat cock trying to get deep into my buns and his grunting increased. I may have been pushing back at him, I'm not sure. I knew what was about to happen and I didn't want to sleep in a wet bed or have my back covered. And there was no way I was going to take it inside my ass, so I spun around and asked him if he wanted me to put it in my mouth? I didn't wait for answer. I just slide down and put my mouth around the head. I'm glad I did not have time to think about it as this was not the plan either, but here I was with a hard cock in my mouth. And there was Jeff, exploding in my mouth right on cue. I clinched my cheeks and swallowed the warm fluid.
Everything happened so fast my own boner went un-noticed. I stood up, pulled my panties off, wrapped them around my cock and jacked off while looking at Jeff's limp and spent dick. Jeff quietly watched me finish into my panties then left my room. Nothing was really said.
Saturday morning was awkward to say the least but we agreed to go get fast food breakfast. We sort of talked about what happened Friday night. I did my best to explain my actions and he did his best to explain his reactions. We agreed that it was "night of secrets" and never to be spoken of again. Merely a night when four full balls were emptied.
The afternoon was uneventful for the most part. Drove around town, listened to the radio and ended up on the local National Forest Park roads. Jeff pulled into a roadside pull off and turned off the engine. He wanted to know more about my cross dressing. I told him that panties felt and looked good but didn't really hold "a guy" in very well so I was always careful with my choice of pants or shorts. He said he agreed that the panties felt good while he rubbed off on me and my quick action took him by surprise. He asked me why I only put the head in my mouth and I told him that I had no sexual experience in that area but I always had vision of super sucking just the head. I asked him how it felt and he said it felt good but he was going to blow his load either way at that point. We both laughed.
I reminded him that my dressing was for me and not for other guys and that he was the one and only male I had been with although it wasn't much of a date. We both laughed again. He also wanted to know why I stared at his spent cock while I jacked off. I said probably for the same reason he laid there and watched me stroke while I was staring at his limp dick, the dick that just gave me my first load of man juice. Sometimes, things are just what they are.
We had about an hour before the games started so Jeff suggested we head back to the cabin. I suggested a quick hike in the forest. There was a trail right behind the pull over so away we went. We were certainly alone in the Park so I took the opportunity to let him know that I thought he had a nice cock even though it was dark and quick. He thanked me for that and mentioned that seeing my fully shaven crotch was a bit of a turn on. I tried to explain that I had no plans of doing that or how it even happened, but what's done is done. He smirked and said he was glad it happened.
I pushed us towards the side of trail and put Jeff between a large tree and myself. I pulled the waistband of my shorts out to show him that I had changed my panties. Just a quick tease peek. Then I started to rub his groin area and said I deserve the chance to see his trimming skills in a better light. You know, I showed you mine now show me yours. Another moment where we both ended up stunned.
He was timid about this but having his crotch rubbed loosened him up. He let me open his fly button and pull his zipper down without much hesitation. I worked his jeans down over his thighs and dropped to my knees and started my inspection. I quickly commented that his trimming skills needed practice. He laughed and said his girlfriend said the same thing.
I apparently have a new fascination with limp cocks. As I kneeled there staring at his soft manhood my fresh panties started getting wet. I was frozen in place until it started to grow. He was getting a hard on right in front of my face.
Then Jeff said, well now what? I responded by fondling his tool and thinking about sticking it my mouth balls deep. But he didn't shower so the crusty fluid remains and scent were still there. I wasn't sure what to do. In my mind I wasn't doing anything. In reality I was stroking him right in front of my face.
He started moaning something about my sweet mouth and pushing my head forward with his hands. My plan was to just lick the tip but Jeff just stuffed it in. I pulled back a bit and probably gave him the worse blow job ever (first time you know). I felt the tension building so I pulled him out of my mouth and stroked him with a fury until he finished on the ground. After a few minutes I stated that it was time to go and that he needed a serious shower.
Back at the cabin Jeff said he was going to jump in the shower. I said "me first" and that he should go into town and grab us some Subs and Salads for the games. He agreed and headed out. I jumped in the shower and stayed in there for a long time. I dried off and started thinking about tonight's outfit. I only brought a few things so my choice was easy. Bikini cut panties, purple bra, dark leggings (for under the short shorts) and slip-on tennis shoes and the short hair bangs wig. A tight crop top that will show that there are breasts under there. No make-up because I have little practice at that anyway. Just a mask and round rim glasses.
Jeff returned just as they were kicking off and went straight to the shower. I would dress later so at this point I was going commando under my sports shorts and T-Shirt. I approached the shower door and asked if needed any help washing up. He laughed and replied that he had been "helped" enough in the last 2 days. But he did ask if I would help him trim someday. I said yes when we had access to the proper equipment.
I went to couch and watched the game while he finished up with the shower and came out in his sports shorts and jersey. We ate our meals on the couch and watched the games. Of course, Jeff was drinking his beer during and after our meal. At half time I announced that I would be in bedroom for a few minutes and would return before the second half.
Once in the room I stripped and started to dress for the evening. I slipped on the panties first and then the leggings. I wish I had brought some nylon stockings but leggings were all I had. They add shape to the legs and hide the leg hair (I do not shave my legs). I slipped the bra on and placed the silicone inserts into the cups. I need something better than this in the future. I put on the little crop top and started to get the wig in place. Nothing is easy about this. Even X Large size female leggings are very tight, large size panties are tight and the wig takes several minutes. I grabbed my glasses and mask and was ready for to present myself fully dressed to another person for the first time. I took a couple of deep breaths and opened the bedroom door.
I casually entered the room just in time for the second half kick off and sat on the other end of the couch. I curled my legs up and under me a bit and did my best to present my breasts. As I mentioned earlier, I am not passable by any means other than a nice round butt so I pointed it at Jeff. Jeff was back in his stunned phase and kept staring at my chest. I really wish I had bought bigger inserts but the one's I had seemed to be working.
To bring Jeff out of his trance I explained that I always wanted to be dressed in front of another person. The mask helps shield my non female face and the leggings covered my leg hair. I told him that the fem clothing felt good and I liked it. He said I looked good and that we should have ordered delivery so I could answer the door. I laughed but totally agreed with him (missed opportunity).
I was away from home, watching college football and I was dressed, so I was happy. Jeff was drinking his beer, not saying much but slowing scooting closer to the middle of the couch. I mentioned that the leggings were cutting into my circulation and pushing my panties into my crack. He said I should take them off and I reminded him that they hide man leg hair and they are much smoother to the touch. I took his hand and placed it on my leg and ran it up and down my thigh and said "see how much smoother and sexier"? He agreed and continued to rub my thighs. I straighten my legs and kicked off my slip-on shoes.
Then throwing caution to the wind I flipped over him like a reverse lap dance and pressed my stuffed bra right into his chest. I was careful not to put my face in his face. I said he could touch my breasts as I rubbed his crotch with my crotch. His sports shorts left little to the imagination. He was getting another boner so I flipped again into a proper lap dance position and began to gyrate. Another sexual activity I had no experience with but I was giving it all I could.
He begged me to take off the leggings and grind him some more. I stood up right in front of him and started to remove the shorts and leggings. I had to bend over to remove my shorts and then again to remove the leggings. He was rubbing my panties while I was removing these articles of clothing. When I was just in my satin panties and shirt, I reminded him that things may not be as attractive from the front as they are from the back. He didn't look at the bulge in my front, he just pulled me down on his lap so the gyrating activities could continue.
I mentioned that we had crossed many lines this weekend. He said I started it by pulling my panties down the day before to show off my hairless crotch. He followed with the fact that I was riding his crotch pretty hard even though the game wasn't over. I quickly reminded him that the first sexual act was when he snuck into my bedroom and started rubbing off on my sleeping ass.
I asked him what else he wanted and replied by reaching in my panties and touching my very tight hole. I said "no". Even though I got through having his cock in my mouth twice that is far as is goes. This was about the time he reached into the front of my panties and started stroking my hard cock. My head was starting to spin. It feels great when it's someone else's hand.
None of this was the weekend plan but here I was grinding on a boner and being stroked at the same time. I said I would let him fuck my mouth and he said "been there, did that" as he rolled me onto the floor on my knees. Jeff came around to the front of me, dropped his shorts and pointed his manhood right at my mouth. I thought I was in the clear and I tried to suck his cock better than before.
Plus, this position allowed him feel up my fake breasts. Even though I didn't get as much out it as I thought I would it was nice to have my boobs massaged. I said he could suck on them but he had other plans. Little did I know that his plan was to use my mouth just to get his dick wet.
He reached for my butt and ripped my panties clean off, pushed me down on my elbows and swung behind me. I was shocked for what might be happening. I was a little afraid but I didn't move. I may have actually raised my ass up some, not sure.
He spread my cheeks and told me to reach back and hold them spread. It shocked me when I did just that. I was fully presented to Jeff, just as he wanted. He rambled off a few slut comments and I fired back with a comment or two about him wanting to fuck his friend straight up the ass. Then he began pushing his cock against my very virgin butt hole. He pushed and rubbed, he rubbed and pushed and it wouldn't go in (whew) until all the attempts pushed him over the edge and he squirted all over my crack. I dodged a bullet but didn't say anything. He collapsed and left me with a thick coating of extremely warm fluid all over my still virgin butt. I could feel it running down my legs.
I gathered my composure, grabbed the ripped panties and wrapped them around my aching member as I straddled Jeff's chest. I jacked it right in front of his face while performing another reverse lap dance on his limp dick until I shot off into the ruined panties. I should have shot it onto his face for forcing me into an attempted doggie position butt fuck session. But either way, my tight little hole is still a tight little hole and we both emptied ourselves.
I think we laid on the floor for 30 minutes when Jeff noted that the game was over. He also stated that we would be sleeping in the same bed later that night. I said "fine but you better go get some lubricated condoms".
Jeff was out the door on his way into town to find a store and I laid there wondering what I had gotten myself into.