** This is based on true events. My first time writing about my experience. I have added my fantasies to a few instances which did not take place but I wish they would have. To be true more than 80% of this story is true with actual events. **
A bit about myself, I am 29yo married to a beautiful woman of 28. My name is Vince. I am 5′ 7″ with an athletic skinny body. I weigh about 128lbs. Due to the pandemic, I have grown my hair until neck and usually tie them together. I hardly have man hair on my body with no facial hair. At a time when I do crossdress wearing lingerie of my wife at home when she is gone, I do pass for a very feminine body and look. My workout at Crossfit has kept me in good shape with the right body curves for man and enough for a feminine body. My wife is about the same height and weighs about 110lbs. So her clothes and lingerie fit perfectly on me.
It was summertime and my wife and I were ready to leave for our long weekend cottage trip. Living in downtown Toronto, we always took the opportunity to escape city life and enjoy some time to ourselves. This time it was different as my whole life changed during our stay of 3 days at the cottage. It started with us leaving on Friday evening just before the September Labour day long weekend. My wife and I headed to our regular spot (The Blue Mountains, Collingwood ) which took us approx. 2 hours. We reached at around 5 pm, got settled, and started to turn on the barbeque at the deck. We usually rent a cottage which is few kilometres off the highway backed by the lake view. This time our cottage was located on the slope which was 2nd from the lake on top. This means our cottage was pretty close to the lakeside and had it’s one side facing the large balcony with deck and large windows of this massive cottage above us on the slope. It means they had a direct view of our cottage which had large windows. The front was facing the gravel road having car parking and loading zone with the other 2 remaining sides having tall trees. The back was a ravine with huge trees and going onto the woods.
Just as we started to put on the barbeque, my wife got a call from her clinic. She picked up the call as being in the medical profession, you are expected to be on call for any emergency to your patients. She had a brief discussion and then hung up.
She came to me and said, “Honey, I have to leave as my patient is in critical condition and the supporting doctor has been called for another emergency.”
I was a little disappointed as this was the last long weekend of summer and we had plans to spend it erotically by trying different positions. However, due to the nature of their work, I respected her decision and see her off. As she was directly headed to the hospital, she left her clothes at the cottage to be used when she will be back on Monday evening. I had 2 full days and tonight to myself. I thought of trying something new and challenging this time.
I had tried to crossdress many times at home wearing my wife’s clothes and looking into the mirror but never outside. I thought I have my chance today and started to think of various situations I can enjoy.
To start with, I turned off the barbeque and went inside to see what my wife had left me behind. She had brought a few Victoria’s Secret lingerie and a pair of baby dolls and a couple of high heels. She had also got few shirts and loose pants with a body-tight swimsuit. I quickly went to the bathroom, grabbed the razor, and shaved off the hair off my legs and arms. I had few hairs at both places so shaving them off would not raise doubts to my wife after a couple of days. I also made sure to clean the place near my cock. I then applied the moisturizer on my whole body and wrapped up the towel from the chest down to my thighs. Just the way my wife does when she comes out of the shower.
I directly went in front of the dressing table and sat there. I saw that the window behind me was regular size and was open having direct access view to anyone who would have seen. Due to the private cottage, no one was allowed access to the backside of it which made me relaxed thinking of not getting caught, however, the cottage behind us was having open space on the second floor with french windows which made it easy for them to see everything going on in the bedroom and other areas of the cottage. Due to the difference between the height of floors (Our rental cottage having ground floor rooms and cottage behind us with the first and second floor) and also the location of both properties on the slope (Our’s on the lower end of the slope than the one behind) the view of my place was restricted to half the size of the room (meaning anyone watching could only see me half from the chest down).
I made a slight turn to see if anyone was standing on the balcony or near the window which would give them my view. To my surprise, I was only able to see a balcony deck with a table and few chairs which were faced down to the table (seemed no one was around there) and the large window had reflection from the sun (It was only 6:15 pm and due to summer sunset happens around 8:45 pm) on it which made it impossible for me to figure out if anyone was standing behind it or not. Thinking about being watched or caught crossdressing by a neighbor made me excited (not that I knew them and would have trouble facing them) which gave it more courage to carry on with what I had planned.
I opened the bag and took out a black panty with a red border and a small red bow on the back. I slid my right leg in it and then the left to slowly pull it up opening my towel when I reached the spot. It felt so soft on my skin as I had just shaved and applied lotion throughout to make it look more feminine and shiny. Now I was sitting in front of the dresser with my back facing the window on a square-shaped box wearing only black panties and nothing else. I grabbed the hairdryer in front of me and started to blow my hair, while doing it, I felt the feminine version taking over me. I then grabbed the matching bra which was 34C in size. It was a regular t-shirt bra that would wrap around my boobs leaving minimal room as I barely had boobs to fill in the gap.
By now I was pro putting a bra on slid both my hand in the strap and got it up resting on my shoulder. Took the hook and moved my hands behind locking it in one go.
Adjusted it to fit me and feel the soft mesh fabric around me. I had done my hair sideways just like a girl to give me a perfect feminine look. I stood up to have a full view of myself in the mirror. My cock perfectly sitting in the panty as it was not fully grown gave a great look. The black Victoria’s Secret lingerie felt so smooth on my skin having a perfect bodily curve with 34C on top and a waste of 30″.
My wife always said that I had feminine love handles and that she was jealous of them of me. I opened the drawer of the dresser to keep the hairdryer in. A small thing rolled out from the drawer. It seemed a small pointy thing – definitely not a dildo (Not that I have used it but seen it many times online) I grabbed it to have a closer look. It had a greasy substance applied to it. After looking at it for a while, I finally figured it was a butt plug. The previous renter had left it behind. Ohh my, I immediately released the butt plug as I realized that I held a butt plug used by some random person in my hand which could have not being washed. Just as it rolled a little far away on the floor from me, a thought of using it came to my find. This thought slightly excited me making me semi-erect.
Without any delay, I grabbed it still facing sideways to the window not giving front exposure. I went to the washroom and washed it with hot water and cleaning it came out. I had never used this before and was curious to see the effect of it on me. I tried to now hold the dresser table with both my hands and then slightly bent forward to open my butt cheeks. Then I grabbed the plug and moved my hand behind. From another hand, I moved the side of the panty opening my ass to it. I looked in the mirror and saw my face turn red with the excitement and feel of the plug touch my anal. I tried to push it in but it barely went inside. I took a deep breath and then held it tight and with my other hand move my butt cheek sideways to open my anal as much as possible. It was painful when the whole thing slid in but then I was determined to try it. It did give me a feeling of excitement when completely in. I adjusted the panty again and stood again in front of the mirror.
I walked out of the bedroom to the living room when I realized it was already 7:45 pm and that I had to start with the barbeque. I always wanted to wear lingerie under my clothes and go out. The thought of getting caught or being watched by women or men who realize what I have been wearing inside gave me a different rush in my body every time. Today was the day to bring my fantasy to life. I grabbed my half sleeve white shirt and light grey shorts.
The bra was not visible from the shirt unless I wrapped my hands around the shirt to cling the bra and make it slightly visible due to the black/red color and a slight bulge on it. I tied my hair as I usually did being a man and headed outside to start the barbeque. The wind was normal but every gust of it had a different effect on me as I was being cautious of not making my inner clothes visible to anyone. Time was flying by as I was being very cautious of my dressing, not realizing that I was alone and nobody was watching me. I finally decided to not think much and act normal.
Just then I heard a voice from my left side “Hello! That smells nice.”
It was the neighbour from the large cottage who saw me outside and wanted to start a conversation.
I replied, “Yes it’s seasoned spicy potatoes and marinated chicken breast”.
Hearing these words he replied with a weird smile “Chicken breast does smell great.”
I simply replied saying “I will barbeque roast one for you. These are marinated by my wife with her special seasoning”.
He thanked me and winked at me. That was weird but then I thought it was normal for his age as he seemed around his 60’s retired and just came to enjoy the time. Just to give everyone a quick view There was a metal fence approx 5″ tall between the two cottages making them separate but still visible of everything. He was sitting in his pullback chair with a beer in his hand. It was already 8:15 pm and it was obvious that he already had his dinner and was now enjoying his beer while I spend time to make my fantasy come true and was preparing for food now. I saw him a couple of times turning towards me and trying to find something. I couldn’t figure it out but then I was not interested to know either as I wanted to relax.
After some time I took the prepared dinner near the fence calling him “Hey, I hope you are still hungry as I just got you the specialty of this season.”
He stood up from his chair and started to walk towards me. He smiled and took the plate from me. He wanted to personally thank the person who invented the dish my wife Lindsay. I told him she was gone out for a personal reason and that I was alone.
He quickly turned to surprise and said “Ohh I thought she was with you as I saw you guys pull up a few hours ago and unloading the car.”
My expressions changed as I feared what could come next. But just then he said “Never mind, I guess you are here to enjoy the last few days of summer. This is a great cottage as many people come by every season and then some are repeats as they love the location and the neighbor he again winked and made a chuckle. ahahaha”
I agreed saying this is a wonderful place as it has lots of activities to do.
He continued saying “How could I forget to introduce myself. My name is Greg and I bought this cottage 5 years ago. My wife and I came here every summer to spend time but since she passed by a couple of years ago, it has only been me visiting this place since then.”
He wanted to talk and make friends as it seemed he had no one to or else who would share details of his dead wife when they are on vacation. Anyways I tried to make it sound that he was living the life his wife wanted at this cottage and tried to escape the conversation. As soon as I turned to leave, there was a ripping sound of something and was loud enough to be noticed even by Greg. Both of us turned back to see what it was and at that time I realized how much trouble I was in as it was my shirt that got caught in one of the hooks of the fence as it was to my chest height and might have got stuck the time I reached out to offer him food.
The shirt got ripped from the second button to the left pocket making my bra cup of 34C visible. Greg on the other hand saw this and stood there not knowing what to say. I quickly tried to remove the shirt from the fence and held it to my chest, trying to find words to say and explain what happened. It seems like a microsecond to me when all this took place but in reality, it was fair about 5 seconds. This was enough for Greg to realize that I was wearing a bra inside the shirt. I think I said something like “These hooks are not bent properly. I hate that my favorite shirt is now torn.”
Just then Greg cut me and said “So was it, not your wife?” and paused there with a questioning face.
I was not sure what he was referring to and instantly said “No, my wife and I are together. But didn’t I tell you that she was away for personal reasons and had to leave?”
While I was saying this Greg’s eyes were fixed at my chest as the torn shirt was flipping out due to strong wind and I was not able to hold the full part as it was bigger than my hand. It gave him a nice look of the inner line of bra having a red border and black strap on me.
He said with a different tone “We both know what I am saying.” Deep inside I knew what he was referring to by watching me wearing my wife’s lingerie and also inserting a butt plug. But I did not dare to speak up.
I stumbled trying to say “I think you…. mission..”
He again cut me and with an affirmative voice said “I know what you are and I think I can help you. Why don’t you come by my cottage and I can help make your stay more exciting!!” I had nothing to say. I turned and started to walk.
“Hey, Vince. I am sure Lindsay would love to know about our little encounter here,” he said.
I stopped and turned to him asking how did he know my name?
He said “The cottage I was renting was his brother’s and he is the caretaker of it. He has the list and contact details of all visitors.” Just as he finished saying this he took out his phone and clicked a picture of me holding my torn shirt barely covering my bra. He added saying this will surely be a good conversation once your wife sees it. I knew I was caught in the worst situation as now he has my photo which could ruin my marriage. I came close and asked him politely, how about we make a small talk tonight like a grown-up man and sort this out.
He burst laughing “Like a MAN, hahaha. How about you come to dress the way I want you to and then we can talk.”. I agreed instantly as I wanted the day to end as quickly as possible.
He added “Wear your girly clothes and just arrive here in them and nothing else. You can use the back door from here if you want or being the girl you always wanted to be and come from the front letting everyone watch you.”
I agreed and walked into my cottage when he yelled from far ” Make sure you don’t remove what’s in your butt.”
I entered the living room and sat there for few minutes analyzing what had just happened to lose my appetite. That’s when I realized that he had seen me getting dressed in the bedroom and because I was facing the dresser and had a similar length of hair like my wife, he thought it was her. And I could not see him as the sun rays reflected his window making it impossible for me to view if he was standing behind. After some time I gathered the courage to face what was coming next. I stood up and walked to the bedroom. Closed the curtains and sat in front of the dresser completely undressing.
I opened the bag and took out all my clothes. I picked up a bright red Vctoria’s Secret babydoll. It was a very fine thin messed fabric with lightly pushed-up cups. The straps were very thin and satin red. The back was completely open except for the hook to close similar to the bra. It had a matching red satin thong which I wore first. It barely covered my cock from the front but then I was not worried. I then pulled up babydoll and slid the thin straps on my shoulders and then closing the hook from behind. I adjusted the length. From the front, it had a clear view of my chest and slight cleavage which appeared due to the pushing of the band and the cups. I could have made a great front view in 32B I suppose.
Down the front was full mesh fabric covered slightly above the mid of my thigh making thong visible. The back was open until the top of the butt cheeks except for the hook. It only covered the butt from behind in length. My butt was giving a good shape due to the plug inside and also constant squats during my workout. I did my hair to complement the look.
I stood up to have a clear look in the mirror. I could not believe this lingerie perfectly fit me and took my body shape. It did give a slightly feminine look. Yet something was missing. I open the bag again and found my wife’s makeup pouch. I opened the cherry lipstick and applied it (Was the only one I could find). Then grabbed the mascara and applied it to my eyelashes, it enhanced the look.
There were other beauty products but did not know how to use so left them alone in the pouch. To my surprise, my wife also got a jewelry box. I found a chain that had 3 different sizes of chains in it. So wearing it had the first one right at the start of my neck and then second a little bigger and then the third reaching my cleavage. Also found a bracelet which I wore on my right hand. I don’t know why but I just got excited and got carried away and to get all dressed up. Lastly, I wanted to finish by wearing heels, but couldn’t find them of my size. I decided to go barefoot.
It was already 9 pm and past sunset so the light got dim but not completely dark. I reached the door but did not dare to open the door the way I was dressed. I took a deep breath and turned on the knob to open the door. As soon as I stepped out, a cool breeze of wind blew past turning me on wearing this sexy outfit. I gathered the courage and walked out to the back of the cottage. There was no one as I stayed in the second cottage from the lakeside and the back of all cottages were facing the ravine lots or reserves with tall trees.
I had to walk to the end of the lot and then open the fence door and enter Greg’s cottage. I walked slowly barefoot on the grass thinking as soon as I leave this cottage, things will change for me. I will expose myself to Greg in full view and he can demand anything of me. As I was thinking, I reached the fence door. Without taking a second thought, I opened it and crossed the fence. I could see few people sitting near the firepit about 7-8 cottages away. I could not imagine they can see me from that far, but by now I was not afraid and wanted them to see me dress as a woman.
I walked past the backyard and, reached the back door of his cottage. My heart racing and mind thinking this is it. Either you knock on the door which will change your life or go back and tell Lindsay everything (Maybe she will understand). But my fantasy of getting caught and submitting to someone took over and my hand reached to knock on the door. It seemed like Greg was expecting me as he appeared tight away from the other room. He opened the door and looked at me. I could say he wasn’t expecting I would come or even put on such a show for him. He let me in and walked behind me checking me from the back.
I was amazed at how big his cottage was as it had a massive ceiling and chandelier in the main room. While I was walking looking up, I hit the couch and bent forward to take support at which point Greg got a clear view of my buttplug still in. He quickly came and grabbed my hand and showed me the way. He asked me to sit on the couch with him and went to prepare the drink.
I would say Greg was well built about 5″ 9′ and 180lbs. Seemed he worked out even now to be in good shape. He was wearing a golf shirt and pants. He came to me with scotch and 2 ice cubes in it and offered it. I took it from him and chugged it right away as I was nervous about what will happen next. He sat beside me with his glass in his hand. I realized that I drank my scotch even before he could sit. He smiled as he sat near to me. He asked if I wanted another drink to which I said not at this time. I could smell him near me.
Looked like he took a shower and was ready for me to arrive. My breath got heavier and was obvious to him as he looked at me in my eyes and put his one hand on my lap and asked to relax. His direct touch on my thigh got an adrenaline rush in my body. His hand was firm and I could feel he let it sit there with heavy feeling to calm me. I made myself stable and looked back to him in the eyes to make sure he understands that he cannot force me to do anything against my will.
He calmly said “Vince I did not believe you would come. But I should admit that you look amazing in this outfit. You are so feminine that you surpass most women I have seen.”
Somehow his words seemed pleasant to me and slightly calmed me down. I kind of smiled and blushed a little came naturally as I was in the character. Slowly he started talking about himself and his wife and how they met. How he fell in love with her and that he misses her a lot now.
By now it seemed like a normal conversation and I think an hour had passed by as I was already 3 glasses down. I could not figure out how but I was sitting closer to him than first I sat maybe he came closer each time he went to grab a drink for me. I did not mind him sitting closer to me as I had my legs folded and occasionally he would touch me on my thighs and at back or maybe rub his hands on my neck flicking my hair.
After some time he got quiet and stopped talking about his wife. Seemed like the more he talked he went quiet. I wanted to make him feel better so I held his hand and smiled. He looked back and came closer to me. He grabbed my head from behind and brought his lips near me. I suddenly realized what was going to happen and moved his hand from my back. It was weird for him as he was not expecting this from me. Before he could say anything, I stood up and walked to the bar, and poured a drink for both of us. Brought back the glasses and gave him his sitting very close to him and keeping my one hand on his shoulder. He did not understand what happened but went with the flow.
He chugged it and took a sigh from it resting his head on the back of the couch. I moved my hand on his face to help him relax and as soon as he closed his eyes, I slowly moved my other hand down his pants and unlocked the belt. Moving both my hands I unbuckled his pants and unzipped them. As I tried to pull it down, he realized and look at me with a smile. I looked him back and blinked my eyes in satisfaction showing him the trust I had now. As his pants were down, I could see his semi-erect cock starting at my face and the warmth of it was pulling me near. I grabbed his shaft holding my hand and started to pull it down. I could see him close his eyes again and let me play with it. I moved close to it and opened my lips to lick the top of it. Slowly moving to the side and down to his balls to lick them up. I could feel the warmth in his cock as it grew bigger and thicker. It was almost 7″ long and had decent size thickness.
By now his cock was erect and facing me straight as I was leaning on his one leg from the side and grabbed his balls and cock on the other hand. I move the shaft up and down and started to suck. I could feel his breath increasing slowly. After few pumps, I stood up and came in front of him and on all fours. This gave him a better view and control over me. Without any further invitation he, grabbed my head from the back and pulled me closer to his cock holding my hair. I took the whole of it in my mouth. It was big and think. I did not expect it would go in but to my surprise, I was able to take it deep in. I never thought I would give someone a blowjob and also enjoy it at the same time. By now he was fucking my mouth.
His cock was so wet with my gagging and saliva that the balls were dripping in them. I grabbed his balls and sucked them dry and slowly moved again to his cock. This time I only worked on his upper shaft to relax it a little. Greg bent over and moved his hands on my back. with both his hands on my back, he could easily grab me and moved me towards him. I was not facing him and without any delay, he grabbed my head from behind and kissed me.
His kiss felt amazing and, made me, excited and got me erect. My cock was pocking out of my thong from the side. At the same time, the butt-plug did its job and gave me another electric moment. Greg knew what to be done and so moved his one hand to my butt-plug and moved it up and down and using his second hand pushed me back to suck his cock.
I started to pace myself sucking his cock up and down to bring him to climax. After few pumps, I tasted his pre-cum and knew he was near to release it. I kind of liked the taste of his pre-cum but did not want him to unload inside me. I pulled my head up and Greg realized it trying to push me back. I suddenly snapped my head back releasing his cock. I was out of breath as I used a lot of energy to release myself. I was sitting my on legs in front of him. Greg saw me out of breath and took this opportunity stood up and brought his cock in front of my face. I was so excited that I would cum with him, so I opened my mouth and let his cock in again thrusting it. He held my head from behind to make sure I finish sucking him to dry. I did not mind this time as I was very excited and wanted to release the load.
Just a few more full thrusts deep throat sucking and Greg’s cum started to shoot inside my mouth. The first release hit my throat deep down and at the very back. The second thrust was thick and just kept coming. I had no time to swallow all of it and so it started to drip out from the side. Greg made sure he emptied every drop in my mouth and then remove his cock. But since my mouth was overflowing he removed it out and thrust the last load on my face.
By now I was covered completely by his cum in my mouth and overflowing out to my chin, throat, chest, and going to my feminine boobs. The one on the face was little and covered a portion of my cheek on one side. He looked at me and smiled moving his hand on my head. Look at him, I swallowed the one in my mouth and even licked the one on the cheek using my finger. I rubbed the one on my chest and boobs to show him he painted me in his cum. This was like a fantasy of mine for a long time to be sucked in a way I saw on porn videos but never thought I would do it myself to a man.
Greg was relaxed and lay down on the couch. I stood up and sat beside him putting my head behind the couch to relax. I just realized that my excitement to cum did not reach climax and was satisfied by finishing Greg. It was already 11 pm by now and Greg offered me to stay as it was cold outside. I accepted his offer and went to sleep with him in his bed. Rest will be continued in the next chapter with my imagination. So far it has been true with everything in detail as to how it happened. The next morning I grabbed the courage to open the front door of Greg’s cottage and walk past the gravel road to my own. I think a couple of young guys in the woods saw me walk past wearing the only lingerie and messed up in drips of mascara and shiny cum over my chest.
I hope you liked the story firsthand from me as it was my first experience and I am now an official cocksucker.