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Dublin: 2°C Saturday 27 November 2021

The Diaries: The 20-something man going out with a transgender woman

“This morning woke up snuggling with my partner…

Image: Shutterstock/GU_Ani

This article contains content of a very explicit nature. 

EVERY NIGHT THIS week as part of our Sex Week series TheJournal.ie will be running a seven-day diary submitted by readers.

The Editor asked each diarist to anonymise their entries but to be as honest as possible in terms of activities and thoughts.

The diaries have been lightly edited for style and length but are the diarist’s own words.

Tonight, a man in his 20s who is going out with a pre-op transgender woman…


“This morning, woke up snuggling with my partner so that got us excited we exchanged oral with each other and went for a shower together (nothing sexual in the shower although it can be playful. The showering together is more practical than anything else and quicker).

“I work in an office with 18 women and one male (me). It’s an extremely open and safe space to discuss sexuality. They usually spend 30 to 40 minutes every two days exchanging stories or banter and asking questions or complaining to me about men and just want a ear.

“When I got home me and my partner had a bit of a makeout session in the kitchen while waiting for the Chicken Maryland to finish.

“And that was Thursday – nothing happened at night just went to sleep. Of course, when you sleep as a male big spoon there will be some horny thoughts before bed because of the closeness to your partner.”


“It was a busy day at work so did not really feel anything sexual. Friday is my partner’s girls’ night so when she got home her libido was very high.

I was awakened with a lovely sloppy kiss of garlic and cheese chips breath so I gave her oral.

“She was returning the favour and then I fell asleep. I was so tired it took my partner two minutes to cop on I was asleep. As I was too silent, she woke me up and gave out to me for falling asleep haha.”


“It was fight night so that was the day really. My partner was hungover in bed and I was going around collecting drink and food for the night. We had a couple of friends over and we played strip beer bong, which is a lot of fun. How it works: couple A loses to couple B then couple B decides what sex act couple A has to perform on each other in front of the winners. Or say couple A loses then the husband performs oral on the winner’s wife or the wife performs oral on the winner’s husband.


Nothing – just painfully hungover so only some mild cuddling.


“I came home and was just wrecked from work so nothing happened. I had a small make out session with my partner.”


“I prepared for anal and my partner topped me in the morning. It was pretty intense I came from my prostate being massaged.”


“On Thursday night, it was my turn to top. It was more sensual than Wednesday.”

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About the author:

The Diarist

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