Travelling

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Cross dressing discovery.
1.2k words
4.49
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vinceh23
vinceh23
206 Followers

I am a retired widower and have been taking road trips of a week or ten days through the west. This trip took me to Arizona and today I was in Scottsdale looking at a property I own there.

I had checked the property and spent the night in a nice hotel and was having breakfast at a nearby coffee shop. I like to wear panties and bras and have gotten rather bold lately, wearing a bra with forms. I am a big guy and it isn't real obvious, though, if you look you can tell.

I was wearing a blue oxford shirt with a white bra, so I didn't think it was too obvious.

The restaurant was crowded, and I was shown a just vacated booth in the back. I had set up my Kindle to read while eating and was looking at the menu deciding what to order when the waitress, a pretty middle-aged woman, asked if I would share my booth with, indicating with a sweep of her hand as she said, "this nice gentleman."

Ted was a nice-looking man in his early 60's, dressed in khaki cotton trousers and pink cotton oxford, like my blue shirt. Not wanting to be churlish, and thinking I'd just as well talk with someone than eat alone, I said "of course." Ted was a local who had moved to Scottsdale from the San Francisco Bay Area recently. He, too, was a retired widower, enjoying his leisure time in that desert community. The small talk progressed easily throughout breakfast and we got to the dating and women aspect towards the end. He had dated a few ladies but nothing serious. There is an easy openness with strangers as we know we will never see them again and don't really care what they think of us. He talked about friends he had and then, looking at my shirt said how many of them liked to wear lady's underwear. Some cross-dress completely and asked if I did that too.

I was a bit taken aback, but secretly thrilled that he noticed and brought it up. I replied saying I just like wearing the bra and panties and had no desire to try to be a woman or dress completely. It was then that I looked closely and noticed the outline of a bra under his shirt. It must have been pink because there was no color contrast. He noticed me looking and said, "yes I am wearing a bra."

"That is why I am sitting here, Vince. Lisa, our waitress, knows I like to wear bras and had noticed yours and thought we would enjoy being together.

I have wondered just how often women notice my bra. Of course, they would never say anything, but I do wonder what they are thinking.

As I had no specific travel itinerary Ted suggested I stay a while and meet some of his friends, take in a few art shows and other "things to do" in Scottsdale. Maybe even go shopping for bras and panties. We both get a thrill of buying bras and panties from sales women, wondering if they are even thinking about it at all. Or, just making a sale. I have gone to Lane Bryant a few times and have been fitted for a bra. At one store, the sales woman was very interested in the fit and wanted to help a great deal, adjusting the straps and cups. She wanted to sell me matching panties and had her helper bring the panties and wanted to see both on me. I was wearing my own black panties, and wore the new ones over that. I got a real thrill out of that little encounter.

We wandered to a few places and Ted suggested we go back to his place for lunch. We could wander around in our bras and panties together.

Ted was about my height, 6 feet but a few pounds lighter. A nice-looking man, clean shaven with short hair. Neither of us were trying to pass, we just liked wearing bras and panties.

We stood before each other, each pitching a tent in our respective panties. We came together for a hug, to feel our tits, he had put in some inserts and was a C cup like me. I felt his bra strap, a thrill in itself, I even enjoyed it on women, then down to his panty clad buttocks. I so love the feeling of smooth nylon under my fingers. I also enjoyed the feeling of his erection against my body. We each wiggled a bit to enhance the feeling.

"That feels great" I said, and he replied that "it sure does. Let me see that boner of yours."

I was wearing white size 8, Vanity Fair panties with just a bit of lace at the sides. My erection visible through the semitransparent fabric. He was wearing black and didn't really expose anything. I stood back so he could see, then got down on my knees to pull his panties down to see his. What a sight. It was at least six inches long, but what girth. I just could not help myself. I had to have that in my mouth and with one hand held it as I wrapped my lips around the head and slid down the shaft. Ted let out a moan of delight as I pulled his panties to his ankles and tickled the spot just behind his hanging balls. I was so excited feeling a bit of pre cim on my tongue. I then pulled his panties back up as I stood up and we kissed. He had soft lips the sensation making for a very sexy kiss. As our tongues started to tangle I felt his hard penis poking my body, making me even more excited. We pulled apart a bit and put our respective cocks in the others panties, adding even more energy to this playtime.

Ted whispered that we should slow down, and I agreed, pulling back and looking at each other, smiles beaming on our faces.

My desire to suck his cock overcame me and I got down on my knees again and took his penis, his throbbing cock, that pulsating member in my mouth and slowly engulfed his erection, tasting the saltiness as I caressed his balls with one hand and began to stroke my cock with the other. His moans grew guttural and he started to thrust. I took my wanking hand and gently touched his anus, that tender spot men have, and Ted just bucked and started shooting his hot semen in my waiting mouth.

The next moments were wonderful, his hands were gripping my head and he was moaning with pleasure. My mind was totally absorbed with sucking his cock and swallowing his cum. It was slippery, tasty and so very sexy. My hand was stroking my rigid penis with ever increasing lust as I, too, started to cum. The whole of the action so very sexy and thrilling.

We finally finished and sat on the floor together, panting through our big smiles, as we recovered from our sexual excitement.

We both knew that more was to "come."

vinceh23
vinceh23
206 Followers
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BiGuyNextDoorBiGuyNextDoor9 months ago

I’m thinking how nice it would be if the waitress, Lisa, would show up. You mentioned that she was middle aged and pretty. Probably wearing some sexy panties and bra herself.

AnonymousAnonymous12 months ago

I love this story and have come back to it many times. And cum. I love wearing a bra but I’m too shy to go out.

AnonymousAnonymousover 1 year ago

very nice its great when a plan comes together

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