Thelma and Me Summer of 65 part 2
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The Surprise In The Summer House free porn video
(Caution– a story with a lot of non-porn, non-quick turn-ons, written by a non-native English speaker)
Each year the summer house needs to be opened up, including all the necessary work. Sometimes my city neighbor volunteers to help me with the work. I return the favor by providing free and ample food and booze and let him and his family spend some holidays there. Because of the virus it was late in the year, when I decided to go. My neighbor unfortunately had no time, but offered his 23-year-old son could join me. He is a bit disoriented as university is pretty much closed and his future is uncertain. Since weeks he sits in front of his computer and smartphone, so some fresh air and exercise would help. I did know his son since c***dhood, and we always went along ok. To be sure I talked to his son whether he really want to come along. I realized that he was not his usual cheerful self, but that he was also not too depressed. I said to him, although both of us had very limited outside contact, we should still be on the cautious side, keep distance and might even wear masks and gloves, when working closer together. We need to fix some wood on the house, paint, bring the boat into ship shape and into the water. I also got some new fire wood, which we have to cut in small pieces. I said he could stay on the second floor, where my daughters usually stay and I will be on ground floor. Late afternoons will be free and we could take his mountain bike with us. That cheered him up and we agreed to leave the day after tomorrow.
Before we started, I suggested he takes the back seat to have more distance. I never was a talker during driving, which annoyed my family, but which suited him, because he was occupied with his smartphone anyway. When we arrived, I noticed that we will have quite some work to do. We were late in the year, so everything has grown significantly and there were quite some storms at the coast, which caused damages. The positive side was, that the longer days have already warmed and dried the house. We had dinner together, some discussions and a couple of beers.
Day 1: We worked hard and stopped about 3 o’clock. I wanted to go for a bike tour, but he wanted to stay and relax. After a couple of kilometers, I noticed a lot of rare birds on their rest before flying to the northern parts of the country. So, I went back to the summer house, fetching the camera. I announced myself that I am back to get the camera. Shortly afterwards I bumped into him. He has not heard me and was standing with ear plugs in front of the mirror, half naked wearing some clothes of my daughters, stockings and a skirt. The most astonishing thing was the big bulge in the skirt. It was very awkward situation. We both apologized. He was very embarrassed, so I told him, he should not be. It was my fault forgetting my camera. He could do whatever he wanted, when he is alone. And I will tell nobody, what I have seen. I said, let’s have a coffee and get over it. Fortunately, we started smiling about our special encounter. I said, it really did not matter, what just happened. He then opened up. He told, that he liked to dress as a woman, from time to time. It turns him on wearing ladies’ clothes. But he feels also embarrassed, guilty about it. He does not want to be “gay” or “kinky”. It does depress him, that he has this urge to wear woman clothes and even enjoys it. I asked him, if his parents or others do know. He said no, and he presumes they will detest it. As he still lives at home, he cannot act as he wants. I told him, he should take it easy and befriend himself with his situation. Sexuality is a strange thing. There is not one normal. There are fetishes, special behaviors, turn-ons, techniques which are not really explainable “in full daylight” or rational discussions. And that each man and woman have different mixes of “male” and “female” hormones. There are men who are quite feminine and women who are quite masculine. If he wants, we could talk later more about it, after my bike tour. On my tour, I thought a lot about what happened. I hoped, that this occurrence did not destroy our relationship and that he did not do something foolish. When I came back, I was relieved, that he was still around and did not escape, out of embarrassment. He was dressed normal, no make-up and preparing meals. I told him which birds I have seen, opened a bottle of wine and we sipped our first glass. During the good meal, we drank more and getting relaxed. He explained that the suppression of his “strangeness” is probably the reason of his depressed mood. I explained, that this is not worth the pain. He would have several options. Talk to his parents about it or find another place to live and finish quickly his studies. As long as we are here, he could wear women’s clothes and find out whether his mood gets better. I will give him money for his work and that tomorrow he could shop clothes he likes to wear. He cheered up.
Day 2: We worked at the house and drove in the late afternoon into the next bigger city. We agreed to meet three hours later, so we have enough time for ourselves. I went to the local museum, which had an interesting exhibition, aswell as to a photo and a book shop. When we met again, he had several bags and was very excited. He got everything he wanted in the department store, second hand and specialty shop. We bought some take away food on our way home and ate it, with some beers. Then I let him enjoying his shopping and said to him, when he feels ok, he could show me his bargains. Indeed, after two hours he came down. I could not believe my eyes. He had a brunette wig on which fitted perfectly to his brown eyes, long eye lashes and a nice make-up. A beautiful woman. Even the walk was quite womanly. He asked me whether he looks good? I told him, that he looked very attractive. We had a night cup together, and called it a day.
Day 3: We worked on the boat and we brought it to sea. As it was a nice day, I suggested to do a boat tour. He brought a bag with him and when we were out at sea he went under deck and returned as – a girl in a bikini. Again, he looked good. He put a lot of sun milk on and asked me to do his back, which I did after washing my hands. He had very smooth skin. I took off my shirt too, and he applied sun milk in return. After being out two hours, we got a tan and returned. He went to the house to cook meals, whereas I cared about the boat. When I came back, he had changed again into a pretty woman and we had meals together. After a glass of wine or two I suggested to him that he could reach out to other “girls” or like-minded men of his age to enjoy their likeness. He could do it via social media and under a pseudonym. I’m happy to do some nice photos of him or even videos. He said, that he would enjoy posing. So, I took the camera and started shooting. He could see the pictures live on the computer screen, as I have a wireless connection camera. We both were amazed how photogenic he was. He really played with the camera, as I encouraged him to do so. We transferred the photos to his computer and he spent the rest of the day selecting the best ones and starting to write a description of him, to be used in social media. I also analyzed the photos and saw that his left side was the “better” one.
Day 4: He behaved different. More self-confidence, smiley and happy. He contributed actively and suggested improvements in the work-flow. In the afternoon I took more photos of him, in different clothing’s. Also, videos. In a tight dress he showed a bulge again. We laughed about it. He said his clothes turn him on. But I also enjoyed the views and my little annex showed also some life. We talked about which social media channels he would like to use and whether also naughty channels could qualify. As I have an account in …. I offered him, to have a look in the member area under hash tags like X-dresser etc. He took the computer with him. After two hours he came back, because the computer had no power anymore. He had a red head and was very excited. He said he has seen wonderful things; he also would like to try out. And meet other cross-dressers, she males, transvestites. He asked me whether I could also shoot some kinky photos and videos of him, that he could use as reference. He also mentioned that on my profile, there are many videos and pics he would like to mimic. I asked him which ones, he preferred most. He mentioned several ones: close shots from every angle and walking around. And some other hot stuff, but he would not like to mention now, but may be later, because he is still a bit shy about it. I said that’s fine, we already a have a lot of work to do. We started with the close ups. He looked very sexy. I encouraged him to take some clothes off. Then I told him to walk around more or less naked. There he hesitated and said he feels uneasy, me full in clothes and him naked. I said no problem and took of my clothes. When he walked around, he got an erection and I too. We both enjoyed it. He mentioned that I have a much bigger cock than him. I said mine is thicker but not really longer and we both laughed again. The longer the session went the more excited we got with dropping precum from our cocks. I said I need to jack off otherwise my balls will hurt later. He said, he too. Then let’s do it together, I said, we could watch us, doing it and I could film him shooting. We sat opposite in different chairs and started slowly to masturbate. I pinched also my nipples, caressed my balls and tickled my anus. After few minutes we climaxed, more or less together. We were both exhausted and agreed to relax on our own. Later on, we met to have dinner and wine. I said I feel a bit strange because we masturbated together. May be shouldn’t have. He said, he feels the same, but on the other hand it was stimulating and interesting for him. How I played with myself, with my cock, nipples, butt hole and how I exploded. And he was a bit proud that he seemed to look so convincing as a woman, that I got so excited. I said he looks really fantastic. He said he would never have thought I would act like I did. I asked him about what was his earlier impression about me. Well, he has seen me always as very rational, serious. Because I am so big, masculine and controlled, one would never expect emphatic sexuality. That I have an interest in bisexuality. I said my main interest is in women. I worship the female body and female sexuality. I like all types of women, but especially mature ones. I like also an erect phallus, especially in combination with the female body. A stiff cock proofs excitement. Typically, when I see one, I get a bit excited, too. The empathy to experience pleasure. That is the reason, why I like seeing him with a bulge or walking around naked with his stiff cock. I can feel his pleasure, just by watching. He asked me whether I had ever sex with a man. I said not outright, but fooled around together with a woman and her partner. He said, that he would like to be fucked, whether I could imagine doing it. I said I could, when he is dressed like a woman and the situation is right. He said, he would enjoy that I would practice with him, because I am so understanding and gentle and wanted immediately to go change into women’s clothes. I asked him to wait. There are lot of things to consider. There is the virus, there is my thick cock, which is not easy to take without pain and preparation. And there is the emotional side. The fucking could mean an extraordinary bonding situation. We could fall in love with each other, which is unacceptable. I am married, too old for him, and the friendship of our families could be destroyed. So, let’s go step by step. I am happy to share my experience with him and help him to go forward in his “sex” life. But not more. He said, he understands. He likes me but does not see the “danger of real love”. He sees it playful. He starts to accept, that his sexuality is ok and that he will move forward. He wants to live his desire. He will finish his studies quickly, find a job, move into his own place and live his good life. He is sincerely motivated now. I showed him a way. And he wants to meet people, who have a similar orientation. Ok, I said, tomorrow, we go to the next adult shop and buy helpful stuff. I explained how sex needs preparations, not to hurt and being messy.
Day 5: He was very quick with his tasks so we could go earlier and buy the stuff. In the shop, we bought lube, condoms, enemas and a smaller but plug and dildo for him, and bigger ones for me. I also bought some flavored condoms. He was interested in strap-ons. I explained that he might find a woman, who is ok with his urge to dress from time to time as a woman and have anal sex with him. Then she could strap the dildo on her and fuck him. What is in it for her? Well if she loves you, she will bring you pleasure, get her clit stimulated and may be feel good, because she is the one to penetrate. Some women like it. In the lingerie section was a black corset, a half bra and black stockings on sale, which he liked very much. We asked the shop assistant, whether it could fit him? He said yes, because it was adjustable. He said that there were also black high heels on sale, which are also available in bigger size. So, I bought everything. On the way back, he said that he was astonished how professional the shop assistant was, and that he did not laugh at him, buying girly stuff. Well, I said, you see, that he is used to it, and you are not alone with your tastes. At home, I explained to him how to use the enema and that we should meet again in two hours clean, with a butt plug applied and dressed for adventure. I also used the enema, showered and put on the butt plug, my black leather boots and a black leather wasp I still have from my biker days. I put blankets on the sofa chairs and put the lube and the condoms, a bucket, black rubber gloves and masks at the side of the chairs. He came down in his new gear, very excited and with a big hard on. I filmed and photographed him parading. What a sight. I wanted to fuck him on the spot, but fortunately could hold my breath. He was also positively astonished, seeing me in my outfit, which of put my cock in the foreground. I ordered him to sit down in the opposite chair and do exactly what I do. I spread my legs showing the butt plug. Then I pumped my cock and played with the butt plug. That was too much for him. He shot a big load of semen on his body and even on his face. I smiled and said that he seems to like what we do. I slowed down my exercise, knowing that he will recover quickly at his age. And indeed. After about 10 minutes he was rock hard again. I removed slowly my butt plug and throw it in the bucket and lubed the dildo. I played long with the dildo just caressing the outside if my anus. It’s such a good feeling. Then I entered very slowly the dildo and let it rest for a minute. He did exactly the same, and I enjoyed watching him pushing and pulling the dildo in an out, in and out again. And then I started fucking myself with the dildo and going deeper and deeper. He came again quickly, but I was now concentrating on myself and did not stop. I had a very strong orgasm. He was very puzzled, first about his own experience but also about my show. I said to him he knows now basically the trick. We met later again for dinner and talked about our experience. We were a bit shameful, but not too much. He said he would now even more like to be fucked by me. He would also like to suck my cock. I asked him when I ordered him to do something, how he felt? Did he like to act as a sub? Would he like more of that kind? He quickly affirmed and I agreed to introduce him gently into this different world next time. He wanted to come closer to me and cuddle, probably also kiss. But I had to stop him and remind him, we have to stay cautious, because of the virus. The risk was very low, because we were now a couple of days together and have been healthy before, too. But I wanted no danger of getting ill and also feared that we could enter emotionally in a deep affair. To help him grow and have some sexual fun myself was enough.
Day 6: The house was now in much better shape. We had painted two sides already so we took the liberty in the afternoon, to follow the same procedure as the day before. But I had a long sleeve shirt on, did wear a mask and rubber gloves, and had an old pair of freshly washed jeans on, in which I cut a hole to show my cock with a condom on and my butt plug applied. When he came down, I ordered him to also wear the same stuff like me, I already had laid out. That will protect us widely from skin contact and it looks sexy, too. I said he should come over to me. He walked to me, with his semi erect cock directly in front of me. He probably thought I will suck him, because he breathed heavily. And I did briefly. Then I commanded him to turn around and bent over. His ass was now directly in front of my face. It looked nice. I took his butt plug and turned it, pulled it and shove it back. With my other hand I pumped his cock. Then I hit him on his ass cheeks, still my other hand around his cock. His cock did no go limp. Then I pinched his nipples. His cock did no go limp either. I increased the pressure and also the hitting, and he even got more excited. So, both of us, know now that some pain could increase his pleasure. I removed his butt plug and wanted to see how he accommodates my bigger dildo. I played quite long with his butt crack, and then shoved it in slowly. He took the big dildo courageously and later on enjoyed it really. Shortly after his anus spasmed, and he shot his load into the condom.
I sent him over to his chair. After a while, I removed teasingly my butt plug and walked slowly to him, stopping just so that my cock was nearly touching his mask. Does he still want to suck my cock? If yes, pump your cock and caress my balls and butt and anus with your other hand. Do you want my cock in your mouth? Then remove your mask and lick the head of my cock. I had a flavored condom on, so he liked it even more. Then I took his head in my hand and asked him to open his mouth, because I will now fuck him orally. But he should go on pumping his cock and with his other hand finger my still lubed anus from the removed butt plug. I fucked him slowly and gently, but as he got accustomed, I was putting more force to it. He moaned with pleasure and I joined in. Within minutes I had my orgasm in his mouth and he climaxed, too.
As he was now ready for the real fuck, I asked him if I could buy him some nice wobbly silicone breasts, because that would make him even more fuckable from my point of view. I have seen them in the adult shop. You pull them over your head like a second skin and they look very natural if you hide a little bit the edges.
Day 7: So next afternoon we bought the stuff and he looked gorgeous. I filmed him extensively and I got very, very randy. We went to bed and I sucked cock. I then ordered him to lie on his side, and I lay behind him. I lubed my condomed cock and his anus and started to penetrate him extremely slowly. I reached around and massaged his cock. He gasped a lot, because my member was even thicker because of all this excitement. When he was accustomed to my cock, I lay on my back and asked him to mount me. He could better do what pleasures him and I could see his lovely cock and big breasts. It was really wonderful how my cock disappeared in him and despite the masks we could see each other into the eyes. This is my favorite position. Shortly he shot his load. I told him to stay put because I was pretty sure he will be stiff soon again. I admired his looks and gently squeezed his cock. As his anus was so tight and he looked so sexy, my prick stayed hard waiting for his revival. So indeed, the show started again and after a couple of minutes I orgasmed and with my helping hands, he climaxed too and shot his load into the condom. During his orgasm he squeezed my cock in several waves, which massaged my cock nicely. We were both very exhausted, but very satisfied. After cleaning ourselves and our gear, we dressed and had dinner together.
Day 8: We were working hard and I had the feeling that he was even in a better mood. After work, we took a boat trip to a nearby small island. As it was a weekday and quite early, there were not a lot of people on boats. As nobody seemed to be around and it was warm and sunny, we removed our clothes, put on sun oil, which made us already excited. We decided to go on a little tour, with our blankets, some food and wine. We had fun with each other by wanking our cocks during walking. Suddenly we met a naked couple in their 50’s or 60’s, also walking. They looked at our stiff cocks and said, what a nice sight to relax the situation. We all laughed. She had a nice laugh, very nice breasts and he a long cock, who seemed to enjoy walking naked, too. She took her man’s cock in her hand and said teasingly that if wanted to be stiff like ours? And indeed, he started to grow. As I liked to see her breasts dangling around when wanking her man, my cock kept stiff. So, the situation was not embarrassing at all, but developed interestingly, due to her wits and boldness. She noticed clearly that I liked to see her and that her partner was not put off. Why not share a little time with each other? They were also equipped with food and blankets, so we rested a few meters apart. They had their summer house not very far. After some drinks, we were getting more relaxed and she said that both of them like sex very much, and that they still try to vary their sex life. As we might have noticed, she is the active part and also somewhat dominant. What about us? Are we gay or bi? I said I prefer women, but I also like cock. My friend said that he discovered recently to enjoy cross-dressing including “gay” sex and that I helped him to come to terms with it. She said that all this is very exciting and may be we could have sex together? I said, we do practice “safe sex” because of the virus. That includes everything like masks, rubber cloves, condoms, top hygienic standards and no kissing for example. She said that this sounds very responsible and understandably. As it was getting colder they invited us to their place later and she suggested that my friend comes dressed as he likes, implying as a woman. We agreed to meet in two hours and went to our boats.
We went home, showered etc., and drove over, my friend dressed as a woman. It was a nice summer house, with a cozy interior. Both of them very extremely surprised by the looks of my friend. They gave him endless compliments. She did wear a very nice red dress, with ample cleavage, stockings and high heels. They offered us drinks and a light meal, and we were chatting amiably. She suggested that the girls will offer a show for us and asked my friend to follow her to the “girly” rooms. After a while they came back. She was wearing long sleeve gloves, over-knee boots, a red corset lifting her breasts, a red mask and – a black strap-on. My friend had also her corset, gloves and mask on, and his cock in condom was showing full strength. They started caressing each other’s bodies, breasts and cocks and asked us whether we liked it. We applauded and had to remove our clothes, put on masks, rubber gloves and condoms. Then they came over. My friend went over to the host, pinching his nibbles and wanking his cock. She did the same with me. Then they started sucking our cocks. Then we had to suck their cocks. Then my friend sucked my cock after cleaning it with alcohol spray, and she sucked her man’s cock. Then I had to go over and suck the hosts cock and vice versa. So, we were all randy like hell. Then she mounted him, and my friend me. It was wonderful watching them fucking. They enjoyed their sex to the fullest. She smiled and screamed and her breasts were wobbling so beautifully. She turned twice around, so I could see her from all angles. My friend was mimicking her and was in full extasy. He looked terrific too. My friend and I climaxed earlier, so we could enjoy their fucking and pleasure undividedly. We smiled at each other and complimented each other. Then we redressed and had drinks together. It was a wonderful evening. Sex can be so pleasurable. We agreed to meet again in future. They said to my friend how adorable he looked and acted in women’s clothes.
Day 9: He activated his profiles on social media. Within hours he got hundreds of friend requests, invitations to chat, video calls and comments. He was very excited and wanted to accept more or less all requests and invitations. I recommended to him, to have a better look on the requester profiles because he does not want to be connected to rude, racist, brutal, psycho etc. ones. On the sex channel, many might see him only as “fuck meat”, have no respect, offend him. I like some kind of “dirty talk” as playful, teasing, stretching limits, but not if it is too abusive, hateful, disgusting. After two hours he came back to me, a bit disillusioned and puzzled and said he now knows, what I mentioned. Requests and comments are still coming in plentiful, from all over the world. Mostly older men, she males, crossdressers etc., only a handful of women. I said laughingly, the world is full of pervy old blokes like me. Funny enough there was one very sympathetic request from a CD living nearby, who detected the spot we shot the outside pictures. His profile was very interesting and it stated that he loves to photograph and film. We had a nice chat with him and we agreed to meet him at the local burger next day at 4 in the afternoon, when the restaurant is usually quiet. The rest of the day my friend was occupied dealing with all the social media request, so I enjoyed myself alone.
Day 10: Today, was our last full day, because he had to leave tomorrow for a university meeting. In the afternoon my friend dressed up as a woman and we went to the burger a bit nervously. He was already there nicely and tastefully dressed as an attractive woman. I went buying the coffee and when I came back, they were chatting vividly. He was indeed nice and I liked him. He said he rarely meets men, because they are often chauvinistic, rude etc. He made the exception, because of my friend, he did find very attractive. My friend said that he should not worry about me. I am very respectful, gentle, emphatic. I was the one, who encouraged him to befriend himself to dress as a woman. And I was the photographer of her. Both of them talked at length, where are good places to shop, how to apply make-up, and whether and how to take hormones. As the burger filled up, we left and went to our house for further talks. I let them alone to chat. Unfortunately, he had to leave at 7 and whether he could redress here, because in the car it is less comfortable. He took a bag from the car and disappeared in the bathroom. After half an hour he returned. Unbelievable. Looking so different. But in doubt I thought he was more attractive as a woman. He wished my friend all the best for his ”coming out” and offered further advice, if needed. We both arranged a photo-tour for Saturday. When he has left, my friend has told me that our new acquaintance was really nice and helpful. He had enquired, how our sex life was and whether I really was gentle and respectful. I should not hesitate to meet him Saturday and develop the relationship further. Then we had dinner together, talked a lot about the last couple of days, but also about many other subjects. We did not have sex together; it was fine without it.
The next morning, I drove him to the train station, because I wanted to stay longer. We were not sad at all. We thanked each other, for everything. My friend was inclined to change his life and meet lots of new people. And I wanted to kayak, sail, read and was looking forward to meet my new friends.
Each year the summer house needs to be opened up, including all the necessary work. Sometimes my city neighbor volunteers to help me with the work. I return the favor by providing free and ample food and booze and let him and his family spend some holidays there. Because of the virus it was late in the year, when I decided to go. My neighbor unfortunately had no time, but offered his 23-year-old son could join me. He is a bit disoriented as university is pretty much closed and his future is uncertain. Since weeks he sits in front of his computer and smartphone, so some fresh air and exercise would help. I did know his son since c***dhood, and we always went along ok. To be sure I talked to his son whether he really want to come along. I realized that he was not his usual cheerful self, but that he was also not too depressed. I said to him, although both of us had very limited outside contact, we should still be on the cautious side, keep distance and might even wear masks and gloves, when working closer together. We need to fix some wood on the house, paint, bring the boat into ship shape and into the water. I also got some new fire wood, which we have to cut in small pieces. I said he could stay on the second floor, where my daughters usually stay and I will be on ground floor. Late afternoons will be free and we could take his mountain bike with us. That cheered him up and we agreed to leave the day after tomorrow.
Before we started, I suggested he takes the back seat to have more distance. I never was a talker during driving, which annoyed my family, but which suited him, because he was occupied with his smartphone anyway. When we arrived, I noticed that we will have quite some work to do. We were late in the year, so everything has grown significantly and there were quite some storms at the coast, which caused damages. The positive side was, that the longer days have already warmed and dried the house. We had dinner together, some discussions and a couple of beers.
Day 1: We worked hard and stopped about 3 o’clock. I wanted to go for a bike tour, but he wanted to stay and relax. After a couple of kilometers, I noticed a lot of rare birds on their rest before flying to the northern parts of the country. So, I went back to the summer house, fetching the camera. I announced myself that I am back to get the camera. Shortly afterwards I bumped into him. He has not heard me and was standing with ear plugs in front of the mirror, half naked wearing some clothes of my daughters, stockings and a skirt. The most astonishing thing was the big bulge in the skirt. It was very awkward situation. We both apologized. He was very embarrassed, so I told him, he should not be. It was my fault forgetting my camera. He could do whatever he wanted, when he is alone. And I will tell nobody, what I have seen. I said, let’s have a coffee and get over it. Fortunately, we started smiling about our special encounter. I said, it really did not matter, what just happened. He then opened up. He told, that he liked to dress as a woman, from time to time. It turns him on wearing ladies’ clothes. But he feels also embarrassed, guilty about it. He does not want to be “gay” or “kinky”. It does depress him, that he has this urge to wear woman clothes and even enjoys it. I asked him, if his parents or others do know. He said no, and he presumes they will detest it. As he still lives at home, he cannot act as he wants. I told him, he should take it easy and befriend himself with his situation. Sexuality is a strange thing. There is not one normal. There are fetishes, special behaviors, turn-ons, techniques which are not really explainable “in full daylight” or rational discussions. And that each man and woman have different mixes of “male” and “female” hormones. There are men who are quite feminine and women who are quite masculine. If he wants, we could talk later more about it, after my bike tour. On my tour, I thought a lot about what happened. I hoped, that this occurrence did not destroy our relationship and that he did not do something foolish. When I came back, I was relieved, that he was still around and did not escape, out of embarrassment. He was dressed normal, no make-up and preparing meals. I told him which birds I have seen, opened a bottle of wine and we sipped our first glass. During the good meal, we drank more and getting relaxed. He explained that the suppression of his “strangeness” is probably the reason of his depressed mood. I explained, that this is not worth the pain. He would have several options. Talk to his parents about it or find another place to live and finish quickly his studies. As long as we are here, he could wear women’s clothes and find out whether his mood gets better. I will give him money for his work and that tomorrow he could shop clothes he likes to wear. He cheered up.
Day 2: We worked at the house and drove in the late afternoon into the next bigger city. We agreed to meet three hours later, so we have enough time for ourselves. I went to the local museum, which had an interesting exhibition, aswell as to a photo and a book shop. When we met again, he had several bags and was very excited. He got everything he wanted in the department store, second hand and specialty shop. We bought some take away food on our way home and ate it, with some beers. Then I let him enjoying his shopping and said to him, when he feels ok, he could show me his bargains. Indeed, after two hours he came down. I could not believe my eyes. He had a brunette wig on which fitted perfectly to his brown eyes, long eye lashes and a nice make-up. A beautiful woman. Even the walk was quite womanly. He asked me whether he looks good? I told him, that he looked very attractive. We had a night cup together, and called it a day.
Day 3: We worked on the boat and we brought it to sea. As it was a nice day, I suggested to do a boat tour. He brought a bag with him and when we were out at sea he went under deck and returned as – a girl in a bikini. Again, he looked good. He put a lot of sun milk on and asked me to do his back, which I did after washing my hands. He had very smooth skin. I took off my shirt too, and he applied sun milk in return. After being out two hours, we got a tan and returned. He went to the house to cook meals, whereas I cared about the boat. When I came back, he had changed again into a pretty woman and we had meals together. After a glass of wine or two I suggested to him that he could reach out to other “girls” or like-minded men of his age to enjoy their likeness. He could do it via social media and under a pseudonym. I’m happy to do some nice photos of him or even videos. He said, that he would enjoy posing. So, I took the camera and started shooting. He could see the pictures live on the computer screen, as I have a wireless connection camera. We both were amazed how photogenic he was. He really played with the camera, as I encouraged him to do so. We transferred the photos to his computer and he spent the rest of the day selecting the best ones and starting to write a description of him, to be used in social media. I also analyzed the photos and saw that his left side was the “better” one.
Day 4: He behaved different. More self-confidence, smiley and happy. He contributed actively and suggested improvements in the work-flow. In the afternoon I took more photos of him, in different clothing’s. Also, videos. In a tight dress he showed a bulge again. We laughed about it. He said his clothes turn him on. But I also enjoyed the views and my little annex showed also some life. We talked about which social media channels he would like to use and whether also naughty channels could qualify. As I have an account in …. I offered him, to have a look in the member area under hash tags like X-dresser etc. He took the computer with him. After two hours he came back, because the computer had no power anymore. He had a red head and was very excited. He said he has seen wonderful things; he also would like to try out. And meet other cross-dressers, she males, transvestites. He asked me whether I could also shoot some kinky photos and videos of him, that he could use as reference. He also mentioned that on my profile, there are many videos and pics he would like to mimic. I asked him which ones, he preferred most. He mentioned several ones: close shots from every angle and walking around. And some other hot stuff, but he would not like to mention now, but may be later, because he is still a bit shy about it. I said that’s fine, we already a have a lot of work to do. We started with the close ups. He looked very sexy. I encouraged him to take some clothes off. Then I told him to walk around more or less naked. There he hesitated and said he feels uneasy, me full in clothes and him naked. I said no problem and took of my clothes. When he walked around, he got an erection and I too. We both enjoyed it. He mentioned that I have a much bigger cock than him. I said mine is thicker but not really longer and we both laughed again. The longer the session went the more excited we got with dropping precum from our cocks. I said I need to jack off otherwise my balls will hurt later. He said, he too. Then let’s do it together, I said, we could watch us, doing it and I could film him shooting. We sat opposite in different chairs and started slowly to masturbate. I pinched also my nipples, caressed my balls and tickled my anus. After few minutes we climaxed, more or less together. We were both exhausted and agreed to relax on our own. Later on, we met to have dinner and wine. I said I feel a bit strange because we masturbated together. May be shouldn’t have. He said, he feels the same, but on the other hand it was stimulating and interesting for him. How I played with myself, with my cock, nipples, butt hole and how I exploded. And he was a bit proud that he seemed to look so convincing as a woman, that I got so excited. I said he looks really fantastic. He said he would never have thought I would act like I did. I asked him about what was his earlier impression about me. Well, he has seen me always as very rational, serious. Because I am so big, masculine and controlled, one would never expect emphatic sexuality. That I have an interest in bisexuality. I said my main interest is in women. I worship the female body and female sexuality. I like all types of women, but especially mature ones. I like also an erect phallus, especially in combination with the female body. A stiff cock proofs excitement. Typically, when I see one, I get a bit excited, too. The empathy to experience pleasure. That is the reason, why I like seeing him with a bulge or walking around naked with his stiff cock. I can feel his pleasure, just by watching. He asked me whether I had ever sex with a man. I said not outright, but fooled around together with a woman and her partner. He said, that he would like to be fucked, whether I could imagine doing it. I said I could, when he is dressed like a woman and the situation is right. He said, he would enjoy that I would practice with him, because I am so understanding and gentle and wanted immediately to go change into women’s clothes. I asked him to wait. There are lot of things to consider. There is the virus, there is my thick cock, which is not easy to take without pain and preparation. And there is the emotional side. The fucking could mean an extraordinary bonding situation. We could fall in love with each other, which is unacceptable. I am married, too old for him, and the friendship of our families could be destroyed. So, let’s go step by step. I am happy to share my experience with him and help him to go forward in his “sex” life. But not more. He said, he understands. He likes me but does not see the “danger of real love”. He sees it playful. He starts to accept, that his sexuality is ok and that he will move forward. He wants to live his desire. He will finish his studies quickly, find a job, move into his own place and live his good life. He is sincerely motivated now. I showed him a way. And he wants to meet people, who have a similar orientation. Ok, I said, tomorrow, we go to the next adult shop and buy helpful stuff. I explained how sex needs preparations, not to hurt and being messy.
Day 5: He was very quick with his tasks so we could go earlier and buy the stuff. In the shop, we bought lube, condoms, enemas and a smaller but plug and dildo for him, and bigger ones for me. I also bought some flavored condoms. He was interested in strap-ons. I explained that he might find a woman, who is ok with his urge to dress from time to time as a woman and have anal sex with him. Then she could strap the dildo on her and fuck him. What is in it for her? Well if she loves you, she will bring you pleasure, get her clit stimulated and may be feel good, because she is the one to penetrate. Some women like it. In the lingerie section was a black corset, a half bra and black stockings on sale, which he liked very much. We asked the shop assistant, whether it could fit him? He said yes, because it was adjustable. He said that there were also black high heels on sale, which are also available in bigger size. So, I bought everything. On the way back, he said that he was astonished how professional the shop assistant was, and that he did not laugh at him, buying girly stuff. Well, I said, you see, that he is used to it, and you are not alone with your tastes. At home, I explained to him how to use the enema and that we should meet again in two hours clean, with a butt plug applied and dressed for adventure. I also used the enema, showered and put on the butt plug, my black leather boots and a black leather wasp I still have from my biker days. I put blankets on the sofa chairs and put the lube and the condoms, a bucket, black rubber gloves and masks at the side of the chairs. He came down in his new gear, very excited and with a big hard on. I filmed and photographed him parading. What a sight. I wanted to fuck him on the spot, but fortunately could hold my breath. He was also positively astonished, seeing me in my outfit, which of put my cock in the foreground. I ordered him to sit down in the opposite chair and do exactly what I do. I spread my legs showing the butt plug. Then I pumped my cock and played with the butt plug. That was too much for him. He shot a big load of semen on his body and even on his face. I smiled and said that he seems to like what we do. I slowed down my exercise, knowing that he will recover quickly at his age. And indeed. After about 10 minutes he was rock hard again. I removed slowly my butt plug and throw it in the bucket and lubed the dildo. I played long with the dildo just caressing the outside if my anus. It’s such a good feeling. Then I entered very slowly the dildo and let it rest for a minute. He did exactly the same, and I enjoyed watching him pushing and pulling the dildo in an out, in and out again. And then I started fucking myself with the dildo and going deeper and deeper. He came again quickly, but I was now concentrating on myself and did not stop. I had a very strong orgasm. He was very puzzled, first about his own experience but also about my show. I said to him he knows now basically the trick. We met later again for dinner and talked about our experience. We were a bit shameful, but not too much. He said he would now even more like to be fucked by me. He would also like to suck my cock. I asked him when I ordered him to do something, how he felt? Did he like to act as a sub? Would he like more of that kind? He quickly affirmed and I agreed to introduce him gently into this different world next time. He wanted to come closer to me and cuddle, probably also kiss. But I had to stop him and remind him, we have to stay cautious, because of the virus. The risk was very low, because we were now a couple of days together and have been healthy before, too. But I wanted no danger of getting ill and also feared that we could enter emotionally in a deep affair. To help him grow and have some sexual fun myself was enough.
Day 6: The house was now in much better shape. We had painted two sides already so we took the liberty in the afternoon, to follow the same procedure as the day before. But I had a long sleeve shirt on, did wear a mask and rubber gloves, and had an old pair of freshly washed jeans on, in which I cut a hole to show my cock with a condom on and my butt plug applied. When he came down, I ordered him to also wear the same stuff like me, I already had laid out. That will protect us widely from skin contact and it looks sexy, too. I said he should come over to me. He walked to me, with his semi erect cock directly in front of me. He probably thought I will suck him, because he breathed heavily. And I did briefly. Then I commanded him to turn around and bent over. His ass was now directly in front of my face. It looked nice. I took his butt plug and turned it, pulled it and shove it back. With my other hand I pumped his cock. Then I hit him on his ass cheeks, still my other hand around his cock. His cock did no go limp. Then I pinched his nipples. His cock did no go limp either. I increased the pressure and also the hitting, and he even got more excited. So, both of us, know now that some pain could increase his pleasure. I removed his butt plug and wanted to see how he accommodates my bigger dildo. I played quite long with his butt crack, and then shoved it in slowly. He took the big dildo courageously and later on enjoyed it really. Shortly after his anus spasmed, and he shot his load into the condom.
I sent him over to his chair. After a while, I removed teasingly my butt plug and walked slowly to him, stopping just so that my cock was nearly touching his mask. Does he still want to suck my cock? If yes, pump your cock and caress my balls and butt and anus with your other hand. Do you want my cock in your mouth? Then remove your mask and lick the head of my cock. I had a flavored condom on, so he liked it even more. Then I took his head in my hand and asked him to open his mouth, because I will now fuck him orally. But he should go on pumping his cock and with his other hand finger my still lubed anus from the removed butt plug. I fucked him slowly and gently, but as he got accustomed, I was putting more force to it. He moaned with pleasure and I joined in. Within minutes I had my orgasm in his mouth and he climaxed, too.
As he was now ready for the real fuck, I asked him if I could buy him some nice wobbly silicone breasts, because that would make him even more fuckable from my point of view. I have seen them in the adult shop. You pull them over your head like a second skin and they look very natural if you hide a little bit the edges.
Day 7: So next afternoon we bought the stuff and he looked gorgeous. I filmed him extensively and I got very, very randy. We went to bed and I sucked cock. I then ordered him to lie on his side, and I lay behind him. I lubed my condomed cock and his anus and started to penetrate him extremely slowly. I reached around and massaged his cock. He gasped a lot, because my member was even thicker because of all this excitement. When he was accustomed to my cock, I lay on my back and asked him to mount me. He could better do what pleasures him and I could see his lovely cock and big breasts. It was really wonderful how my cock disappeared in him and despite the masks we could see each other into the eyes. This is my favorite position. Shortly he shot his load. I told him to stay put because I was pretty sure he will be stiff soon again. I admired his looks and gently squeezed his cock. As his anus was so tight and he looked so sexy, my prick stayed hard waiting for his revival. So indeed, the show started again and after a couple of minutes I orgasmed and with my helping hands, he climaxed too and shot his load into the condom. During his orgasm he squeezed my cock in several waves, which massaged my cock nicely. We were both very exhausted, but very satisfied. After cleaning ourselves and our gear, we dressed and had dinner together.
Day 8: We were working hard and I had the feeling that he was even in a better mood. After work, we took a boat trip to a nearby small island. As it was a weekday and quite early, there were not a lot of people on boats. As nobody seemed to be around and it was warm and sunny, we removed our clothes, put on sun oil, which made us already excited. We decided to go on a little tour, with our blankets, some food and wine. We had fun with each other by wanking our cocks during walking. Suddenly we met a naked couple in their 50’s or 60’s, also walking. They looked at our stiff cocks and said, what a nice sight to relax the situation. We all laughed. She had a nice laugh, very nice breasts and he a long cock, who seemed to enjoy walking naked, too. She took her man’s cock in her hand and said teasingly that if wanted to be stiff like ours? And indeed, he started to grow. As I liked to see her breasts dangling around when wanking her man, my cock kept stiff. So, the situation was not embarrassing at all, but developed interestingly, due to her wits and boldness. She noticed clearly that I liked to see her and that her partner was not put off. Why not share a little time with each other? They were also equipped with food and blankets, so we rested a few meters apart. They had their summer house not very far. After some drinks, we were getting more relaxed and she said that both of them like sex very much, and that they still try to vary their sex life. As we might have noticed, she is the active part and also somewhat dominant. What about us? Are we gay or bi? I said I prefer women, but I also like cock. My friend said that he discovered recently to enjoy cross-dressing including “gay” sex and that I helped him to come to terms with it. She said that all this is very exciting and may be we could have sex together? I said, we do practice “safe sex” because of the virus. That includes everything like masks, rubber cloves, condoms, top hygienic standards and no kissing for example. She said that this sounds very responsible and understandably. As it was getting colder they invited us to their place later and she suggested that my friend comes dressed as he likes, implying as a woman. We agreed to meet in two hours and went to our boats.
We went home, showered etc., and drove over, my friend dressed as a woman. It was a nice summer house, with a cozy interior. Both of them very extremely surprised by the looks of my friend. They gave him endless compliments. She did wear a very nice red dress, with ample cleavage, stockings and high heels. They offered us drinks and a light meal, and we were chatting amiably. She suggested that the girls will offer a show for us and asked my friend to follow her to the “girly” rooms. After a while they came back. She was wearing long sleeve gloves, over-knee boots, a red corset lifting her breasts, a red mask and – a black strap-on. My friend had also her corset, gloves and mask on, and his cock in condom was showing full strength. They started caressing each other’s bodies, breasts and cocks and asked us whether we liked it. We applauded and had to remove our clothes, put on masks, rubber gloves and condoms. Then they came over. My friend went over to the host, pinching his nibbles and wanking his cock. She did the same with me. Then they started sucking our cocks. Then we had to suck their cocks. Then my friend sucked my cock after cleaning it with alcohol spray, and she sucked her man’s cock. Then I had to go over and suck the hosts cock and vice versa. So, we were all randy like hell. Then she mounted him, and my friend me. It was wonderful watching them fucking. They enjoyed their sex to the fullest. She smiled and screamed and her breasts were wobbling so beautifully. She turned twice around, so I could see her from all angles. My friend was mimicking her and was in full extasy. He looked terrific too. My friend and I climaxed earlier, so we could enjoy their fucking and pleasure undividedly. We smiled at each other and complimented each other. Then we redressed and had drinks together. It was a wonderful evening. Sex can be so pleasurable. We agreed to meet again in future. They said to my friend how adorable he looked and acted in women’s clothes.
Day 9: He activated his profiles on social media. Within hours he got hundreds of friend requests, invitations to chat, video calls and comments. He was very excited and wanted to accept more or less all requests and invitations. I recommended to him, to have a better look on the requester profiles because he does not want to be connected to rude, racist, brutal, psycho etc. ones. On the sex channel, many might see him only as “fuck meat”, have no respect, offend him. I like some kind of “dirty talk” as playful, teasing, stretching limits, but not if it is too abusive, hateful, disgusting. After two hours he came back to me, a bit disillusioned and puzzled and said he now knows, what I mentioned. Requests and comments are still coming in plentiful, from all over the world. Mostly older men, she males, crossdressers etc., only a handful of women. I said laughingly, the world is full of pervy old blokes like me. Funny enough there was one very sympathetic request from a CD living nearby, who detected the spot we shot the outside pictures. His profile was very interesting and it stated that he loves to photograph and film. We had a nice chat with him and we agreed to meet him at the local burger next day at 4 in the afternoon, when the restaurant is usually quiet. The rest of the day my friend was occupied dealing with all the social media request, so I enjoyed myself alone.
Day 10: Today, was our last full day, because he had to leave tomorrow for a university meeting. In the afternoon my friend dressed up as a woman and we went to the burger a bit nervously. He was already there nicely and tastefully dressed as an attractive woman. I went buying the coffee and when I came back, they were chatting vividly. He was indeed nice and I liked him. He said he rarely meets men, because they are often chauvinistic, rude etc. He made the exception, because of my friend, he did find very attractive. My friend said that he should not worry about me. I am very respectful, gentle, emphatic. I was the one, who encouraged him to befriend himself to dress as a woman. And I was the photographer of her. Both of them talked at length, where are good places to shop, how to apply make-up, and whether and how to take hormones. As the burger filled up, we left and went to our house for further talks. I let them alone to chat. Unfortunately, he had to leave at 7 and whether he could redress here, because in the car it is less comfortable. He took a bag from the car and disappeared in the bathroom. After half an hour he returned. Unbelievable. Looking so different. But in doubt I thought he was more attractive as a woman. He wished my friend all the best for his ”coming out” and offered further advice, if needed. We both arranged a photo-tour for Saturday. When he has left, my friend has told me that our new acquaintance was really nice and helpful. He had enquired, how our sex life was and whether I really was gentle and respectful. I should not hesitate to meet him Saturday and develop the relationship further. Then we had dinner together, talked a lot about the last couple of days, but also about many other subjects. We did not have sex together; it was fine without it.
The next morning, I drove him to the train station, because I wanted to stay longer. We were not sad at all. We thanked each other, for everything. My friend was inclined to change his life and meet lots of new people. And I wanted to kayak, sail, read and was looking forward to meet my new friends.
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