Dressing and dating

I'm 32 and have been curious about dressing for years. I've only ever been with women but that changed last year. I finally bought myself a pair of women's boots and then clothes followed soon after.

I dressed most evenings in private and started posting pics on Reddit. I loved the compliments from both women and men. After that I started going into Grindr and chatting with men, especially older. I hit it off with one man, he's 61 and a week later we met up for a coffee. Things went fast from there.

He lived alone and provided a space I could dress more regularly and dress for someone in person too. This turned into a regular meet 2-3 times a week and still continues now!! I absolutely love dressing for a man and getting sexual too. I love exploring and sucking cock. It turns me on so much.

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u/Eskimoheels — 8 days ago

Dressing and now dating

I've had an interest in dressing for years. I'm 32 and have been with women most of my life. In the past year however I've changed. I finally got myself a pair of women's boots and then clothing. I love dressing up in private whenever I can.

Over Christmas last year I was dressed one evening and decided to post some pics. I absolutely loved the compliments from men. I felt amazing and turned in. I continued to do so for the following couple of weeks and then found myself on Grindr. I was especially attracted to older men. I hit it off with one man. He's 61.

Things progressed quickly. A week later we met for a coffee and we hit it off. He lived alone and that gave me a space to dress more and dress for someone else. I was over in his house 2-3 times a week, dressing every time. Since then we've got romantic too. I absolutely love sucking cock and being with a man. It just feels so right.

I'm looking forward to exploring the fem side of me more !

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u/Eskimoheels — 8 days ago

I love older cock

Nobody knows but I've been curious for a couple of years now and always chickened out with men. I'm in my early 30s now and recently out of a ltr with a woman and decided it's my time to explore.

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I got onto Grindr and matched with a few guys, I like older men. Matched with one man, he's 61 and I'm 32. I enjoyed our chats and I was happy to see where things went. We met for a coffee a few weeks ago and things have escalated.

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He lives alone so that makes things easy. I call over 2-3 times a week and we kiss, cuddle and I suck him off most a lot. I absolutely love it and love exploring my sub side. I can't wait to take his cock inside me.

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u/Eskimoheels — 19 days ago

Crossdressing for an older man

I've been interested in crossdressing for years. Being in relationships with women though, I never really could explore properly. As of last year I'm single and bought myself more stuff.

At first it was just me and looking/feeling cute. But then I wanted more. I posted on here and got such nice compliments, especially from men. I then found myself on Grindr and chatting with guys. I hit it off with one. He was 59. A top and had a Dom side. Anytime we spoke I'd dress and we'd videochat.

We eventually met up for a drink and really hit it off. I felt so horny and wanted more. A few days later he invited me to his to dress and to chill. I was super nervous but I knew I wanted this. I got to his and got dolled up and we spent the day together. That evening we kissed, fondled and I eventually got to suck his beautiful cock. I sucked it 2-3 times over the night and made him. I absolutely loved the taste of a man's cum. Since then we meet up regularly, I love being able to explore and have fun. So glad I found this side of me

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u/Eskimoheels — 28 days ago

Hooked up with a leather daddy!

I've started dabbling in crossdressing the past few months. More for myself and enjoying how awesome I feel. I started doing it more and grew more curious, I downloaded Grindr.

I spoke with many men and sent pics of me dressed. I enjoy kink and matched with one guy who wears leather and enjoys someone who CDs. We hit it off and spoke for a few weeks before eventually meeting.

We met for a drink first and we went back to his. I quickly got myself dressed up and he got his leathers on. We cuddled on his couch before I sucked his cock & balls for the night. It was such a turn on and it felt so right.

Since then we meet up twice weekly and explore and have fun.

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u/Eskimoheels — 1 month ago

Got with my gay friend

I recently broke up with my ex gf and am going through the motions.

My friend invited me over to chill and watch a movie/vent. We opened a bottle of wine and had a fun night. We were lying on his couch and he lay beside me. I didn't think much of it and continued watching the movie. We finished off the bottle and both were tipsy.

He leant in against me and I started getting hard. Suddenly his hand is on my thigh and he looked at me and leant in for a kiss. I tried to stop at first but I couldn't and let it happen. We kissed for a bit before he took of my jeans and started stroking me, it felt so amazing. I decided to return the favour and I actually loved. We fondled around more and he eventually gave me head. We weren't done there, he asked would I like to suck his cock and I didn't say no. He thought ms as I sucked it and it was so hot.

Nothing is awkward with us since and to be honest I wouldn't mind trying it again

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u/Eskimoheels — 1 month ago

Crossdressing for an older man!

I've been curious to crossdress for years and never actually acted upon it. It all started from a boot fetish I have. My most recent relationship ended early last year with my gf and because I now had so much free time to myself, I bought my first pair of boots. Soon after I was wearing a full outfit with a wig.

At first it was just my private time, but I posted a pic on reddit and got a lot of compliments and I started getting curious. Soon after I found myself on grindr chatting to men. I loved the compliments and being called sexy. I hit it off with one man, older than me but I secretly loved it. We chatted and everything swapped numbers. Anytime I dressed I sent him pics.

A few weeks later we met for a drink and it was hot. I brought my clothes with me and ended up back at his fully dressed and so turned on. That night, we touched, kissed and I sucked his cock twice. It was amazing. I felt so girly.

Since then we've been seeing each other more regularly and exploring more

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u/Eskimoheels — 1 month ago

Met a man at the sauna

I've been going to my local sauna a lot recently for a sauna and cold plunge.

Had a day off work and decided to go early one day. Had the place to myself or so I thought. I was in the sauna and walked in an older man with a dad bod in a towel. Quiet at first but we struck up conversation. We did 15 min and cold plunged a few times. The last round he removed his towel and his cock was....sexy af. I stared and he caught me.

There was a brief silence until he got up and sat beside me. I got so hard. He asked if it was okay to keep the towel off and I mumbled yes. The 15 minutes was up and off we went to the showers, I kept thinking about this man's cock. He was in the shower next to me and I dunno what came over me but I suddenly was knocking on his door. He opened with a smile and pulled me in before long I was on my knees sucking him off.

We both got dressed and he passed me his number before we went our separate ways before he said he'd see me here again soon

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u/Eskimoheels — 1 month ago

Crossdressing for an older man.

I'm 30. Been with women most of my life but for the past 5 years I've started dressing in private. It all started with a boot fetish and it expanded from there.

I recently came out of a relationship with a woman last year. Having more time to myself I dressed more and wanted to start showing people. I'd always thought about cock. I decided to download Grindr and explore. I spoke to many guys and really hit it off with one. He's 56 and he was so complimentary of my style and was happy to go slow. We swapped numbers and a week later we met for a coffee (when I got over my nerves)

We continued to text all the time and anytime I dressed I was sending photos. A few weekends later he asked me over to his for the day to dress and chill, which I did. It was such an awesome day.

We spoke and had drinks. I was so horny we ended up kissing and getting touchy. I was dressed in a top, skirt, panties, tights and boots. Eventually I got around to sucking his wonderful cock and I made him cum three times over the whole day. I found my place lol! Since then we're pretty much fwb for now, I get to go to his and dress whenever I like. And mess around.

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u/Eskimoheels — 1 month ago

Met an older man I was texting

I've a girlfriend. Been curious for a while but that was it. Went out in my city a few weeks ago with work and we got separated as the night went on. Ended up in this bar/club and I was at the bar and got chatting to this older chubby guy.

He's 56 and I'm 30. We got on well and he ended up getting me a drink. He told me he was gay and me being in a relationship didn't really bother him. I won't lie I was turned on. He gave me his number and we went our separate ways

I kept thinking of him a few days later so I decided to text and again our conversation flowed. He suggested meeting up for a coffee. My gf was away so I did. It went really well and he invited me back to his.

I ended up kissing him and sucking his cock. It was so hot and I get so erect thinking about it. He wants to meet up again soon.

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u/Eskimoheels — 2 months ago

Met up with an older guy I was texting

I've a girlfriend. Been curious for a while but that was it. Went out in my city a few weeks ago with work and we got separated as the night went on. Ended up in this bar/club and I was at the bar and got chatting to this older chubby guy.

He's 56 and I'm 30. We got on well and he ended up getting me a drink. He told me he was gay and me being in a relationship didn't really bother him. I won't lie I was turned on. He gave me his number and we went our separate ways

I kept thinking of him a few days later so I decided to text and again our conversation flowed. He suggested meeting up for a coffee. My gf was away so I did. It went really well and he invited me back to his.

I ended up kissing him and sucking his cock. It was so hot and I get so erect thinking about it. He wants to meet up again soon.

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u/Eskimoheels — 2 months ago

Keep thinking about sucking

In a relationship with a woman. However I keep thinking about cock and especially older men.

I was in my gym changing room recently and saw a guys cock. He must've been about 60 but I instantly went super erect. I wasn't even embarrassed but nobody saw.

Since then I keep fantasizing!

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u/Eskimoheels — 2 months ago

Falling for an older guy at the gym

As the title says. Been with my gf for a few years but I'm friends with this guy at the gym and have developed feelings. He's 57. I'm 30.

He asked me for a coffee recently and I went along. He gave me his number and said if I ever want to chat outside the gym to text him. Well I have and now can't stop!

He's very complimentary and always says I'm in great shape and when I wear certain gym fits he says I look great!

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u/Eskimoheels — 2 months ago

Loving cock!

I've been hooking up with an older man for a few months now and I can't get enough. I'm 31 and he's 58.

I was in a relationship with a woman for years and that ended last year. I had curious thoughts for years but never acted on them. Well that changed when I found myself on grindr. I chatted to a few men and eventually met this guy. We spoke for a few weeks and ended up swapping numbers.

We eventually got around to a date and despite being super nervous I loved it. Since then we meet up regularly at this apartment. I suck his cock all the time and I love it. I love the taste of cum. We have stated having sex and having an erect cock inside me is such a turn on. I can't get enough now

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u/Eskimoheels — 2 months ago

My first time dressing in public

So I met a guy who's bit older than me. I'm 31 and he's 55.

We've been chatting for quite some time and I feel comfortable around him. We've been on dates. Well this weekend I'm going to finally bite the bullet and dress for a coffee date. He's encouraging and supportive but obviously I'm still super nervous!

Wish we luck and I love following along in this sub!

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u/Eskimoheels — 2 months ago