01 - Weekend To Remember (Adult Content)

Weekend to remember

I was crossdressing many years ago when I was first married. My ex-wife caught me wearing some of her shapewear and she was not very happy at all. Our marriage was not doing well at that time and her finding me didn’t help. So, I stopped. I have always thought about it but I was scared to do it again. I thought stopping would help our marriage but it really was destined not to be a success.

Some new toys

Give it a year or so later, I had stopped crossdressing, but I stumbled on a porn video which had a woman fucking a guy with a strap-on. I was so turned on, I went out and purchased a couple of dildos. First one was a little narrow and short but, at that time, I took it as a suggestion from the girl at the sex shop as a good one to start with. A couple of months later, I am back at the same shop, talking to the same girl about getting something bigger. But this time I had a plan in my head and I wanted to make sure that this one would fit a strap-on harness. This one was much bigger! It was about 8" long, very thick, and very realistic with proper veins, balls, and a nice large tip. It even felt realistic instead of a "plastic/rubber" feel.

Let me just say that I had many fun nights playing with both of those dildos!

Jump ahead a couple of years later. My first wife and I were separated and I started to date my current wife.

At the very beginning of our relationship, we would have phone sex all the time. I found out that she had her favorite toy (a cock shaped vibrator) that she would bring out. Well, one night and I don't know why, I felt brave and asked her while she used her toy, if I could use one of mine? "Oh wow. You have one? Go ahead!" I was so happy but also shocked with her reaction. I think she was even more shocked when I told her that I had two of them. 

Tell Her I Like to Cross Dress

So, we are on a date at one of our favorite restaurants and I think we must of had a couple of drinks and we were talking about what my ex didn’t like about me and I blurted out that I liked to cross dress and she caught me by surprise again when she said, “Oh really. That is cool.” I was surprised but we kept on talking. She said that there is nothing wrong with a man wanting to wear women's clothing and she said that she would love to see me in some women's clothes some time in the future. I was shocked and so euphoric about what she had said. The conversation ended and we continued along with our date as if nothing weird had happened. Because of that, I didn’t think much about it.

Weekend in Niagara Falls

I think it was only a couple of weeks had passed, and she and I went away for a weekend to a hotel in Niagara Falls. When we were packing, she asked me if I can bring my toys with me in my bag. This woman is surprising me left, right and center!

We had planned to stay for a couple of days. When we arrive at the hotel and get our room key, she takes a key and asks me to get some small things (pop, chips, and stuff) from the convenience store. I agree not thinking of anything.

When I came back, to my surprise, when I walked in the room, laying on the bed was a very sexy bra, panties, garter with stockings, a cute dress and some heels. She said she is going to step out for a bit and asked me if I would get changed for her? Well, **smile** I thought I had died and gone to heaven.

That night started with her giving me a little mini-makeover with some separate make-up that she had bought for me. She said and I thought that I looked pretty good. The only thing she could not afford to get me was a nice wig. She told me that if I was wearing a wig, we might have gone out for a walk.

The night was so memorable because during the evening, we brought out her toy and my toys. Then I noticed there was something new with all of this fun adult stuff and that was a strap-on harness. We played with her toy while I made her cum a couple of times and then she said, "I want to have some fun now". I lay down on my back and spread my legs for her. She got out the smaller dildo and played with my ass. She lubed up my asshole and slid the toy slowly inside me. I was in heaven. As she slid the toy deep inside of me, even she noticed how easily it was sliding and said, "Now I understand why you have this bigger toy but you are sure that I am not going to hurt you." I said, "No you won't. Just take it slow to start and then you'll see me open up for you."

So with that said, she slid the large dildo into the harness and then slowly started to push the dildo inside my tight ass. It felt so big but it also felt so good. She adjusted the angle and then the toy could slide in deeper. It felt so good deep inside of her. She looked me in the eye and she could see the pleasure I was feeling.

With a couple more pushes deep inside of me, I has an incredible anal orgasm. It was incredible! After that, she slowly pulled the toy out of me and then we collapsed together in each other's arms.

The next evening, we came back to our room, after being out for most of the day, to have a rest before going out to dinner. We have our quick nap and both of us start to change and get ready for dinner. She pulls out the bra, panties, garter and stockings out of my suitcase. She turns to me and asks, "Can you wear these tonight under your clothes?" I turn to her and say, "Really? Do you think anyone will notice?" "No." she replies. The only thing that anyone might notice is that you are wearing a bra and no one will think twice about it. 

With that said, I turned to her and said, "OK" and put on all of the lingerie and then my normal clothes. "Turn to me and turn around." As I turned to her and turned around, she says, "You can't even notice. I wonder if we have some fun and give your bra some padding." She goes to her suitcase and pulls out some socks and one of her bras. She takes the lining out from the bra, unbuttons my shirt, stuffs the socks and lining into my bra. She steps back, looks at me and says, "Much better. You still really can't see much but the both of us will know and it will be fun."

We had a great time that night. We went out to dinner and then went to a bar for a couple of drinks. Throughout the night, I was trying to see if anyone noticed my padding and bra.  

Note: This is what I have noticed is that people don't really care or even want to notice. No one really noticed or showed that they noticed or even cared.

As you can imagine, we came back from a great, fun evening and had even more fun. 

Fully Dressed

This continued for a couple more months. We would go away for the weekend, and she would bring along the clothes and the toys. Eventually, we bought a wig and I felt complete. We even went for a walk down the street to find a small bar (**huge smile**) and had a drink. I was in heaven. I was nervous as anything but she told me that I looked good and I passed as a very tall woman (I am 6’0 and I was wearing 2″ booties). I got some strange looks but no one said anything to me or her so I thought it was a success! After a couple of drinks, we would head back to our hotel/motel room and have incredible sex. I would make her cum and then she would fuck me until I came.

Final Thoughts

So, ever since those nights when I felt a dildo deep inside of me, I have always been curious about how it would feel to have the real thing, a nice real hard cock, sliding deep inside me. Fucking my ass and then to feel him shoot his cum deep inside of me.

Also, I want to please a man with my mouth. I have watched many porn movies and read many blogs on how to such a cock and I think I would be really good at it.

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