I Doubt that Those Are Standard Military Issue

Submitted by Anonymous:

Alan and I met through an online dating site. I was skeptical about meeting anyone on there since I’d had a few weird experiences in the past, but this one takes the cake!

The first warning signal occurred before our first date.  Alan asked me out and said that he would text me before the weekend with the details. I never heard from him, so I assumed that he’d changed his mind.

Then on Monday he wrote to tell me that he’d left his phone in his friend’s car over the weekend and just got it back. He asked if I’d like to meet sometime during the week. Despite my better judgment, I agreed. We decided to meet at a bar close to Alan’s house since he mentioned that his car was giving him trouble and he didn’t want to travel too far.

When I got to the bar, I figured Alan would be there since I was running a bit late. As he was not, I sat down to have a drink and wait. I sent him a text to see where he was and to find out how much longer until he arrived. He said that he was only a few minutes away and that he’d be right there.

When he finally walked in the door, 15 minutes later, I was pleased to finally meet him.  He was very tall with a lean, athletic build and deep brown eyes.

Alan began with stories of how he’d spent his years since high school in the military, fighting in the Persian Gulf, and that he was pursuing a career as a surgeon. He told me that he had a scar on his abdomen from where he’d been shot with an AK-47 but his Kevlar vest had protected him and he’d only been burned.

He then told me to feel an area on his thigh under the shorts he was wearing... I expected to feel another battle scar. Instead my fingers brushed up against a pair of satin and lace underpants! Alan then told me that he liked to wear women’s lingerie and that he would also like it if I could use a strap-on dildo on his behind.

My reaction was controlled – I’m in the medical field and have been trained not display my facial expressions when presented with a case that is shocking. I’m also a very open-minded and non-judgmental person so I didn’t want to make him embarrassed. After all, everyone has their own quirks and kinks. But I did find a way to end the date as quickly as possible after that. 

Needless to say, I didn’t contact Alan again and when I finally heard from him several days later, he wrote me a text to say “Where have you been? I left my phone at the gym and just got it back.” I never responded and have also taken my profile off the dating site. There will be no more online matchmaking for me after that!


  1. Alan needs to keep his phone on a leash.

  2. Good thing you sent this to Jared anonymously. Don't want guys blowing up your phone/email looking for the type of chick who's willing to stick her hands up some guy's shorts on command the first time she meets them.

  3. Glad you got away from that psycho!

  4. Were you going to move that hand higher up if the lacies weren't there?

  5. lol I dated a guy like that once. He handed me a box and inside was a vibrator. I said "baby I don't need that" and his response was "it's not for you". That relationship didn't last much longer than your date after that!!

  6. So you finally meet an honest man, and you find his honesty frightening?

    I will never understand white women.

  7. 2:50 Don't be just counting the white women, all women are equal when it comes to not understanding them.

  8. That's right, 2:50 and 3:53. There's no understanding why the entire female sex isn't beating down the doors trying to get at an 'honest' (surgeon / combat veteran? oh YEAH) guy like this one.

  9. Perhaps if his dating priofile mentioned "I'm 100% straight but I like to wear women's panties and take it up the arse" he might have better luck. Just a thought...

  10. Anon 6:04, you're making the huge assumption that this guy is straight!

  11. JD is back...oh joy...now the comment section if FUN again. In HIS mind. yawn

  12. i just LOVE the emphasis 12:07 PUT on his WORDS in HIS post.

  13. well guys, actually transvestic fetishism (as this obviously was) only ever really presents in straight (or occasionally bi) men. he wasn't exactly subtle or tactful letting his date know however lol

  14. Some of these comments come from some obviously close-minded people.

    I happen to be a guy that would love to have a girl use a strap-on on me... and did, in the past. Current girlfriend won't do it, sadly.

    It doesn't feel good because I think it's a real penis -- I've been that route, it isn't actually enjoyable. No, it's enjoyable because of stimulation of the prostate. That, and just like many women who enjoy anal for the same reasons, there are tons of sensitive nerves in the anus.

    A few days ago, I tied her hands up with rope our bed, we had sex, and I covered her mouth with my hand. She pretty much said it was the best sex we had ever had afterwards.

    The whole point of this post: you'll live a happier and more fulfilled life if you have an open mind.

    Anonymous 6:04, I like your post.

  15. Ok, while I see the freakiness factor in that he didn't even get to know you before he pulled this, the actual fetish isn't the freakiness. My boyfriend is into forced femme (I'm a girl) and he loves it up the ass, because that's where the prostate is located. There's nothing wrong with it, at all, ever. It may not be your turn on, but that doesn't make or break a relationship.

  16. ^ Really? Is THAT where the prostate is located? ;-)

  17. My favorite line is "I’m in the medical field and have been trained not display my facial expressions when presented with a case that is shocking."

  18. As a straight woman, I think this guy sounds like a hoot. You found it necessary to end the date "as quickly as possible"? If I was still single I think I'd want his number. As long as he promised not to stretch out my lingerie.

    That been said, Anon 9:34 - I totally agree there's nothing wrong with it, at all, ever, and that it shouldn't make or break a relationship. Sadly, that happens all too often because people tend to be very closed-minded. Sad, really.


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