Crossdressing, Sex and Covid-19 , part 1

Recently I heard from ‘Mary’. A number of years ago we had a brief but interesting friendship and then we drifted apart. To say the least I was surprised to hear from her. I was flattered to hear that she had been keeping tabs on me through this column.

We had met up at a Tri-Ess group meeting in the Orlando area. At that time the group was meeting at one of the resort/conference centers along State Road 192 near Disney World.

Neither of us were exactly Tri-Ess type gals so at an appropriate time we slipped away from the group and headed to the hotel bar. Long story short: we met two nice gentlemen whose wives and kids were at Disney while the boys had been playing golf all day. Well, golf and then at the bar. They were not expecting anyone back until after the Disney fireworks.

It turned out Mary was the flirtatious type and the guys were keen to play along. It also turned out that Mary had a room at the resort and the boys were just as happy not to be seen around the resort playing with two t-gals. Yes, they had read us. So we all went back to Mary’s room. I remember thinking ‘this is weird’ and ‘Mary must have been expecting company; this room is very tidy’.

But as they say, ‘What happens in a resort/conference center in Orlando stays in a resort/conference center in Orlando.’ Mary and I exchanged emails for a while and then like most of my one-night relationships we stopped hearing from each other.

So you can see how it was a surprise for me to hear from Mary.

Her first email was short and a bit of a teaser, ‘I hope you are fine and staying safe in this crazy world,’ it read. Yes, the Covid pandemic was well ramped-up. Half of America was encouraging wearing masks and social-distancing and the other half was crying ‘hoax.’

I was truly happy to hear from her and told her so. Fact is I am always happy to hear from anybody and during the pandemic even more so. My partner has put her foot down about ‘Linda’ going out.

‘Can we Skype?’ Mary asked, ‘I want to talk with you and see you, too. We arranged for a date and time late enough in the evenings that our partners would be in bed. I also wanted to look good and I know Mary would, too. We only had to meet once to know that ‘present-ability’ if not ‘pass-ability’ was important to both of us.

At the agreed time we were both there on Skype. Right away I noticed why she wanted to Skype. “My God, did you have a boob job?” I exclaimed.

“Nice, aren’t they,” she replied. “I ordered them from the Breast Form Store,” she replied, “They come as a molded set. Isn’t that cleavage nice? No more taping for me.”

I remembered how we had discussed the trials and tribulations of using athletic taped to achieve a cleavage illusion. Ohhh, the pain when a tape job was too tight or stayed on too long!

“They are really nice,” I concurred, “How do your men like them?”

“Well I know one guy who likes them to see them and like you he thought I’d had a ‘boob job’ as you call it but I haven’t yet given them the heavy-duty test and that is what I’d like to ask you about. I know you are good and careful with your advice.”

“You flatter me,” I smiled. “How can I help?”

Mary launched into her story. “I was out at our nearby Ross store — thank you by the way for turning me on to them — I was looking at the dresses and thinking of temporarily buying some to take home for try-on. I was a bit self-conscious as it was my first time out with my new boobs. I was thinking that perhaps I should not be wearing such a low-cut blouse. You know it is not just the men whose line of vision lowers when the cleavage comes out. But I noticed a guy looking at the dresses or was he looking at me, I wasn’t sure.”

I didn’t get to ask her but I think THIS is the style of breast plate that Mary was wearing. Realistic looking isn’t it?

“Isn’t that a pain that Ross has closed their fitting rooms? Good for you finding a way around their ban. I think I must have bought about 50 dresses since their fitting room closure. . .and returned about 48 of them,” I interjected. I quickly got back on subject, “however just like for the GG’s when the attention is unexpected or unwanted the boob watching can be very disturbing, can’t it?”

“I moved over to the kids’ department and he didn’t follow,” she continued, “I guessed it was a false alarm. He just wanted to catch a glimpse of these lovely full babies.

“But when I went over to the lingerie racks there he was again.”

“Was he stalking you?”

“No, this time he did not seem to notice me. He was too engrossed in feeling and sizing up the bras and then the panties?”

“Was he a crossdresser?” I asked.

“My thought exactly. He certainly wasn’t looking at the lingerie or the dresses the way a man would look at them as if he were trying to pick out something for his wife.” She winked.

That was my cue to ask Mary what she had done. I still had no clue why she wanted my advice.

“So don’t tell me you seduced him?” I asked feigning jealousy.

“Not so fast,” she replied. “I knew if I confronted him directly he’d probably bolt out of the store. I asked for his advice. I picked out a bra and held it loosely across my breasts. ‘I want to wear some new lingerie for a friend. Do you think he’ll like this?’ she asked.

“’He’d be a fool not to,’ he replied. I was so glad he didn’t run, that he had the nerve to stay and talk with me. Did I mention he was very cute? It wasn’t until a little later that I figured out that he had not yet figured out that I was TG.”

“Wow!” was all I could say. Those breasts are good, I thought. “So what did you do?”

“I asked if he was buying for a special someone. He replied evasively, ‘sort of’. I pretty well knew then that at some level he was interested in crossdressing.

“Is it for you?” Mary says she asked and of course he blushed but again he did not turn and run. Instead he confessed that it was, that he had a costume party to attend and he asked how she knew.

“Because I’m a crossdresser, too” she had explained to him. Of course he looked shocked and exclaimed that she looked so good. ‘How do you do it?’ he had asked. He told her that when he tried to dress and use make up he looked a mess but she looked so natural.

Mary told me that they were both wearing the protective masks required by the store but she said she could tell by his aqua blue eyes that he was a kind and gentle person.

‘How do I do it?’ Mary says she said, ‘Take me to lunch and I’ll tell you.’ Mary had noticed that he had barely been able to take his eyes away from her new cleavage. She was pretty confident that he would take up her invitation to invite her to lunch. She was right. In that state, restaurants were at least open for reduced indoor dining. They were soon settled at a table but as Mary explained their conversation was as much about life and current politics as it was about crossdressing. They discovered both loved movies and Jeopardy! At that time they were rooting for the late Alex Trebek and they both identified as progressive Democrats.

For most of their time together Mary and her friend were wearing their masks. They did slip them down to drink their drinks and eat their meals but they were cautious, just the same.

Now I’m pretty sure that every crossdresser who gets into a casual date with a nice looking man eventually comes to the question: ‘What’s next?’ Do they settle the bill and agree to meet again? Do they go their separate ways? Or like Mary and I would favor do they find a place to ‘take it to the next level’?

I think most men found Mary to be an enthusiastic bedroom partner because she loved being in the bedroom (if you know what I mean). And this time with her new breasts I’m sure she was anxious to give them a go.

“But here’s the thing,” said Mary finally turning her attention back to me, “in normal times there is no question that I would have hinted that if he found a hotel room we could spend a lovely afternoon together. But these are not normal times. Tell me Linda, Is there such a thing as safe sex in a Covid world?”

“You got me there,” I replied. Since the pandemic hit I hadn’t given much thought to having any casual sex, that plus the fact that my partner was pretty well keeping me under lock and key. “I know we are supposed to keep six feet apart and even six inches distance makes sex difficult for me,” I joked.

“And what about the masks,” chimed in Mary, “kissing seems difficult. A blow job might technically be possible but would it be safe?”

“I have heard you cannot spread the virus through sexual contact but you certainly can through close oral contact so no kissing is a certainty.” I offered.

“Yes, but if I’m lying in bed with a man and we are both wearing masks are we at risk of spreading Covid?” Mary asked.

“Well you are not if neither of you are infected,” I tried to be helpful.

“But I don’t know that, do I?” Mary retorted, “I’m a senior citizen. . .Almost!” she corrected herself, “I’m ALMOST in a high risk group. For all I know he could have been Covid-19 positive even if he didn’t know it.

“But I see I’m not going to get any help from you.”

“Well what did you do?” I asked in frustration.

“We are going to get together again and I’m going to help him dress and pick a femme name. And we are both going to get tested for the coronavirus as well as the usual STD tests that I insist on.”

“That’s a lot of effort,” I commented, “You must really like this guy.”

“He’s nice and he’s a nice retirement project for me,” Mary retorted, “but I’m disappointed that you, my fountain of transgender knowledge does not know how Covid-risky is sex for the average crossdresser. Bye.”

With that Mary was gone. That’s just her style, I thought.

But I also thought that I should look into the risks of casual sex in the Covid world. I’m doing that. You will get my report in four weeks. So will Mary. But what I can tell you now is that according to one leading medical authority it seems crossdressing might play an important role in keeping sex partners safe. They wrote it. I’ll tell you about it. Stay tuned.

Tags: crossdressing, featured

Category: crossdressing