Catherine and Callie
- 2 years ago
- 47
- 0
The First Time All The Way free porn video
I had been crossdressing for a some time but it was only when I became single again that I could really let myself go and have some fun. Most of my earlier fun was with guys meeting in cars and feeling and wanking each other off as I was nervous about taking them back to my house at the time. Then one day I was on a well known crossdressing dating site when a message came in from Vicky. The message simply said “Hi, we live very close to each other and seem to have similar tastes, do you want to meet for a chat”. I quickly checked her profile and we certainly seemed to have the same tastes. I quickly replied and that was the start of a lovely relationship.
It was a month or so later when we were at Vicky’s house having a drink before we went upstairs to have some bedroom fun together when an e mail came through on her phone. “That’s interesting” she said. “There is a new club opening at an old pub only a couple of miles away, its being opened by the same guy who is running a similar place I used to go to but stopped as it was too far away”. She then told me it was a swingers club that has one evening a week for crossdressers and trannies. She used to go there with some other CDs but hadn’t been there for a while because it was about 50 miles away.
It was an hour or so later when we were lying in bed together after another sexy time that Vicky asked whether I would be interested in going to the club with her. I told her I would love to but was a bit concerned about my lack of experience and my nervousness about anal sex which I thought would hold me back as I was still an anal virgin. Vicky told me not to worry as the old club catered for all sorts of people and she couldn’t see why the new one would be any different.
It was the following Friday when Vicky, in male mode, came over to pick me up from home to drive the venue which was an old country pub about 4 miles out of town. We paid our entrance fee and we were shown around by the owner. There was a small bar but the majority of the place was given over to sofas and armchairs. There a small dance floor where a couple of CDs were dancing together. We were then showed to a dressing room where our host left us. I had put my underwear, black stockings, suspender belt, panties and bra, on at home and so it was just the case of taking off my top clothes and putting on my red dress and high heeled shoes on. Vicky had done the same except her underwear was blue with a cream dress and shoes. We sat in front of a mirror and put some make up and our blonde wigs on. We put our bags in a locker and walked out indoor the bar. The place was not very busy with other CDs and admirers yet as we walked to the bar but we certainly turned a few heads on our way. I bought a drink for us, wine for me, a soft drink for Vicky and we chatted to each other for a while getting some admiring glances from a number of other guests.
After about 10 minutes or so there was a lot of helloing as 4 of Vicky’s friend came in. They were all already dressed as they had waited until nightfall before driving to the club. Introductions were made and we sat on some sofas together and chatted and occasionally danced together all evening. Although we got a lot of looks from some admirers nobody came up and chatted to us, whether this was because we looked to be enjoying ourselves too much or it was opening night and people were wondering how things worked I don’t know. It was getting towards the end of the evening when Vicky and I went to the bar to get one last drink when to guys came up and started chatting to us. Their names were Paul and Chris and they were both nice looking but I really liked Paul who was very complimentary to me about my clothes. I had to go to the toilet and when I came back to the bar but Vicky and Chris were dancing together. Paul asked if I would like to dance and we went over to the dance floor. We danced to a couple of R&B songs and then a slow ballad came on. We put our arms around each other and slowly moved to the music. His hands were caressing me as we danced and then he moved his head and said “kiss me”. I opened my mouth and we kissed slowly and passionately, our tongues exploring each others mouths. I could feel him getting hard as he pressed against me as I also was getting turned on by him. The song ended and we went to a sofa in another room. We sat down and Paul started to kiss me, our hands all over each others backs and we pulled each ourselves tighter. Then he moved his hand from my back down to my bottom and squeezed my bum which was delightful. His hand then moved to my thigh and under my dress and back up until he was stroking my leg above my stockings. He almost growled “ I love stockings, they are so sexy”. I could only moan with please and say “yes”. Then I heard a voice saying “It's time to go guys they are shutting soon”. I looked up and it was Vicky and Chris standing watching. We stood up and Vicky said that we could all go back to her house if we wanted to. We collected our bags set off to the car park. Vicky has given the address to Chris and we set off with the boys behind us.
We got separated when we went through traffic lights and the boys were stopped as the lights had changed. We got to Vicky's house and went inside, we looked at each other and I said I wonder if they will come . Vicky went in to get some wine from the fridge and was just coming back out with the bottle as the doorbell rang. We all went into the lounge and Vicky offered wine which only Chris and Vicky wanted, I thought I had had enough, and Paul was driving. Vicky looked at me and said “if you want to carry on where you left off at the club can use our room. “Okay” I said and taking Pauls hand I took him upstairs to the second bedroom where Vick and I had so much fun together. “Excuse me for one moment” I said and I went to the bathroom, when I returned to the bedroom call Paul was just behind the door waiting. He had taken his shoes off, so I was a little taller than him I still have my stilettos on. I slipped them off and we kissed and embraced again our hands exploring each others backs and bottoms. I said to Paul “this dress has a zip at the back”. His hand went to the top off the dress and slowly pulled the zip down. We parted so I could let the dress fall and Paul could see me just in my underwear. He looked and just said “wow your gorgeous”. I said “thankyou” and reached to him and began to unbutton his shirt, then I unbuttoned his trousers and pulled the zip down . Paul took his shirt off and let his trousers fall to the ground, he was wearing black boxer and they had a lovely bulge in them. I just dropped in my knees and pulled his boxes down and over his hard cock which was in front of my face. It was my turn to say “wow you're gorgeous” I took cock in my hand and began to caress it, my mouth opened and took his cock head in my mouth and began to suck him. He moaned slightly as my head bobbed up and down on his now hard as a rock cock from which I could taste pre cum. “Pandora can you stop please as I am not going to last long if you carry on like that”. I let his cock out of my mouth and looked up at him. I knew then that this was a man who I would like to take my anal virginity.
I looked up at Paul and said, “I've never been fucked before but tonight will be the first time if you want to”. “I would love to he said, I have some condoms in my coat”. I stood up and let him get to his coat. Like a gentleman he stopped to take his socks off. He turned around and held me in his arms again. His hands reached in the top of my knickers and slid them down and over my cock. This time it was Paul who dropped to his knees and took me in his mouth. My knees seemed to go week at this and Paul let me go so I could lie down on the bed. He lay down on top of me and we kissed again, he then slid back down the bed and took my cock in his mouth and again. He only sucked me for a short while before he moved down lower and began to kiss my balls and then he lifted my legs to expose my love hole. I felt his tongue licking all around me and then he pushed it into me, I gasped with pleasure as he rimmed me. He then slowly worked his way back up to my balls, cock, tummy, chest and then to my mouth where we kissed open mouth. “Are you sure you want to do this” he said, and I just nodded. He moved back to the bottom of the bed and took a condom out of its packet and rolled it in to his beautiful hard cock. While he was doing this I reached to the drawer of the bedside cabinet and took out a tube of lube which I handed to him. He coated his cock with some and then put some on his hand and said to me “lift” I lifted my legs and he liberally applied lube to my already damp love hole. He shuffled forward and took my legs in his hands and lifted them up and put them on his shoulders. I then felt his cock just touching me as he used his hand to guide himself in to me. I shut my eyes let my arms fall either side in a spread-eagle fashion and said “yes”. I felt his cock head just pop into me and I gave a little gasp, he let slide almost out before pushing again a little further, and then again and again until I could feel he was all inside me and his balls were resting on my bottom. My legs were hurting in this position so we changed to a missionary position, this didn’t last long as I wanted to feel all of him in my so I wrapped my legs around his back and hugged him to me. He started a steady rhythm his cock sliding beautifully inside me. I was enjoying him so much as we fucked, kissed and caressed each other. Pauls breath was getting faster so I knew he was enjoying himself as well, then he let out a huge grown and began to shudder as he came. It was a wonderful feeling as he spent himself deep in me and I hoped it would always be this good. He slowed to a stop and then smiled at me and said “wow, that was so good, thank you”. I smiled back and closed my eyes. After a couple of minutes I felt him slowly slide out of me and he led on my side. I looked down at his cock with the condom still on it but now full of cum. He looked at me again and said “I cant wait for the next time”. “Neither can I”, I replied.
But that is another story………
It was a month or so later when we were at Vicky’s house having a drink before we went upstairs to have some bedroom fun together when an e mail came through on her phone. “That’s interesting” she said. “There is a new club opening at an old pub only a couple of miles away, its being opened by the same guy who is running a similar place I used to go to but stopped as it was too far away”. She then told me it was a swingers club that has one evening a week for crossdressers and trannies. She used to go there with some other CDs but hadn’t been there for a while because it was about 50 miles away.
It was an hour or so later when we were lying in bed together after another sexy time that Vicky asked whether I would be interested in going to the club with her. I told her I would love to but was a bit concerned about my lack of experience and my nervousness about anal sex which I thought would hold me back as I was still an anal virgin. Vicky told me not to worry as the old club catered for all sorts of people and she couldn’t see why the new one would be any different.
It was the following Friday when Vicky, in male mode, came over to pick me up from home to drive the venue which was an old country pub about 4 miles out of town. We paid our entrance fee and we were shown around by the owner. There was a small bar but the majority of the place was given over to sofas and armchairs. There a small dance floor where a couple of CDs were dancing together. We were then showed to a dressing room where our host left us. I had put my underwear, black stockings, suspender belt, panties and bra, on at home and so it was just the case of taking off my top clothes and putting on my red dress and high heeled shoes on. Vicky had done the same except her underwear was blue with a cream dress and shoes. We sat in front of a mirror and put some make up and our blonde wigs on. We put our bags in a locker and walked out indoor the bar. The place was not very busy with other CDs and admirers yet as we walked to the bar but we certainly turned a few heads on our way. I bought a drink for us, wine for me, a soft drink for Vicky and we chatted to each other for a while getting some admiring glances from a number of other guests.
After about 10 minutes or so there was a lot of helloing as 4 of Vicky’s friend came in. They were all already dressed as they had waited until nightfall before driving to the club. Introductions were made and we sat on some sofas together and chatted and occasionally danced together all evening. Although we got a lot of looks from some admirers nobody came up and chatted to us, whether this was because we looked to be enjoying ourselves too much or it was opening night and people were wondering how things worked I don’t know. It was getting towards the end of the evening when Vicky and I went to the bar to get one last drink when to guys came up and started chatting to us. Their names were Paul and Chris and they were both nice looking but I really liked Paul who was very complimentary to me about my clothes. I had to go to the toilet and when I came back to the bar but Vicky and Chris were dancing together. Paul asked if I would like to dance and we went over to the dance floor. We danced to a couple of R&B songs and then a slow ballad came on. We put our arms around each other and slowly moved to the music. His hands were caressing me as we danced and then he moved his head and said “kiss me”. I opened my mouth and we kissed slowly and passionately, our tongues exploring each others mouths. I could feel him getting hard as he pressed against me as I also was getting turned on by him. The song ended and we went to a sofa in another room. We sat down and Paul started to kiss me, our hands all over each others backs and we pulled each ourselves tighter. Then he moved his hand from my back down to my bottom and squeezed my bum which was delightful. His hand then moved to my thigh and under my dress and back up until he was stroking my leg above my stockings. He almost growled “ I love stockings, they are so sexy”. I could only moan with please and say “yes”. Then I heard a voice saying “It's time to go guys they are shutting soon”. I looked up and it was Vicky and Chris standing watching. We stood up and Vicky said that we could all go back to her house if we wanted to. We collected our bags set off to the car park. Vicky has given the address to Chris and we set off with the boys behind us.
We got separated when we went through traffic lights and the boys were stopped as the lights had changed. We got to Vicky's house and went inside, we looked at each other and I said I wonder if they will come . Vicky went in to get some wine from the fridge and was just coming back out with the bottle as the doorbell rang. We all went into the lounge and Vicky offered wine which only Chris and Vicky wanted, I thought I had had enough, and Paul was driving. Vicky looked at me and said “if you want to carry on where you left off at the club can use our room. “Okay” I said and taking Pauls hand I took him upstairs to the second bedroom where Vick and I had so much fun together. “Excuse me for one moment” I said and I went to the bathroom, when I returned to the bedroom call Paul was just behind the door waiting. He had taken his shoes off, so I was a little taller than him I still have my stilettos on. I slipped them off and we kissed and embraced again our hands exploring each others backs and bottoms. I said to Paul “this dress has a zip at the back”. His hand went to the top off the dress and slowly pulled the zip down. We parted so I could let the dress fall and Paul could see me just in my underwear. He looked and just said “wow your gorgeous”. I said “thankyou” and reached to him and began to unbutton his shirt, then I unbuttoned his trousers and pulled the zip down . Paul took his shirt off and let his trousers fall to the ground, he was wearing black boxer and they had a lovely bulge in them. I just dropped in my knees and pulled his boxes down and over his hard cock which was in front of my face. It was my turn to say “wow you're gorgeous” I took cock in my hand and began to caress it, my mouth opened and took his cock head in my mouth and began to suck him. He moaned slightly as my head bobbed up and down on his now hard as a rock cock from which I could taste pre cum. “Pandora can you stop please as I am not going to last long if you carry on like that”. I let his cock out of my mouth and looked up at him. I knew then that this was a man who I would like to take my anal virginity.
I looked up at Paul and said, “I've never been fucked before but tonight will be the first time if you want to”. “I would love to he said, I have some condoms in my coat”. I stood up and let him get to his coat. Like a gentleman he stopped to take his socks off. He turned around and held me in his arms again. His hands reached in the top of my knickers and slid them down and over my cock. This time it was Paul who dropped to his knees and took me in his mouth. My knees seemed to go week at this and Paul let me go so I could lie down on the bed. He lay down on top of me and we kissed again, he then slid back down the bed and took my cock in his mouth and again. He only sucked me for a short while before he moved down lower and began to kiss my balls and then he lifted my legs to expose my love hole. I felt his tongue licking all around me and then he pushed it into me, I gasped with pleasure as he rimmed me. He then slowly worked his way back up to my balls, cock, tummy, chest and then to my mouth where we kissed open mouth. “Are you sure you want to do this” he said, and I just nodded. He moved back to the bottom of the bed and took a condom out of its packet and rolled it in to his beautiful hard cock. While he was doing this I reached to the drawer of the bedside cabinet and took out a tube of lube which I handed to him. He coated his cock with some and then put some on his hand and said to me “lift” I lifted my legs and he liberally applied lube to my already damp love hole. He shuffled forward and took my legs in his hands and lifted them up and put them on his shoulders. I then felt his cock just touching me as he used his hand to guide himself in to me. I shut my eyes let my arms fall either side in a spread-eagle fashion and said “yes”. I felt his cock head just pop into me and I gave a little gasp, he let slide almost out before pushing again a little further, and then again and again until I could feel he was all inside me and his balls were resting on my bottom. My legs were hurting in this position so we changed to a missionary position, this didn’t last long as I wanted to feel all of him in my so I wrapped my legs around his back and hugged him to me. He started a steady rhythm his cock sliding beautifully inside me. I was enjoying him so much as we fucked, kissed and caressed each other. Pauls breath was getting faster so I knew he was enjoying himself as well, then he let out a huge grown and began to shudder as he came. It was a wonderful feeling as he spent himself deep in me and I hoped it would always be this good. He slowed to a stop and then smiled at me and said “wow, that was so good, thank you”. I smiled back and closed my eyes. After a couple of minutes I felt him slowly slide out of me and he led on my side. I looked down at his cock with the condom still on it but now full of cum. He looked at me again and said “I cant wait for the next time”. “Neither can I”, I replied.
But that is another story………
Hester
- 25.11.2020
- 21
- 0
