Ashley_1962
04-02-2009, 06:52 PM
PART III - "Back to the apartment" now posted...PART II Now posted below....
Warnings:
1) This is a long post…
2) This post deals with bisexuality; I understand and support the fact that a large percentage of this cross-dressing community define themselves as heterosexual. I therefore would ask that those who may be offended by this topic a) move on to the next thread or b) refrain from commenting in a negative way.
For those of you who have not read one of my previous posts (http://www.crossdressers.com/forums/showthread.php?t=95731) – due to my cross-dressing and a number of other contributing factors my SO and I agreed to separate sometime before Christmas. We are still living together, and overall the arrangement is ‘amicable’ – and quite honestly less stressful in a number of ways that it was before we decided to take this step; I no longer feel like I am walking around on egg shells – and there is no longer any ‘sexual’ tension between us either.
Since then, I have taken a number of steps to explore my femme side, this has included a few things like building up my feminine wardrobe – made some good progress, but that’s a job that never finishes, improving my femme appearance by getting more comfortable with putting on make-up, tweezing eyebrows, dropping a few more pounds and a few other little things. In addition to focusing on the physical aspects I have also been trying to find someone (anyone??) to a) go out ‘en femme’ with and b) explore/confirm my bisexuality. Well, I finally succeeded – on both fronts!!
Bit of a long story, but I joined one of those on-line dating sites catering to those of us who are interested in ‘non vanilla’ relationships. After numerous false starts and email exchanges I finally found ‘a couple’ that seemed to be just what I was looking for (and more!). When I say, “what I was looking for”, quite honestly – it was a no strings attached bisexual experience while cross dressed; I was/am still not looking to get into a long term relationship. In a nutshell, they are a couple where he is a bisexual cross-dresser and she is a very supportive bisexual GG. They have been in this relationship for several years and have had a number of ‘dates’ with other cross-dressers and also with some GG’s. It actually all happened quite quickly - after our initial email exchange, we chatted about ½ a dozen times to get to know each other better and to work out the details of our date; all of my communication was through the GG. Of course I was very nervous/leery about the whole thing – the list of things that ‘could go wrong’ was longer than the list of things that ‘could go right’ – but somehow I felt that this couple was genuine and not a psycho (or couple of psycho’s) setting me up for who knows what. The positive ‘clues’ for me were that our chats were not focused on sex – more general discussions really about getting to know each other; they did not want me to send pictures in compromising positions etc.. and also a big confidence builder was when she sent the address where they live and we were to meet – I knew it was a very good location; she also provided a cell phone number. The plan (after a few adjustments here and there) was for me to meet them at their condo – I was to be dressed casual ‘en femme’; we would have a drink and chat (or I could ‘bail’ right then and there before entering the apartment..), and then I would get dressed for the evening out and she would do my makeup for ‘going out on the town’ (did I mention that she also does make-up as a side job?) . After meeting at the condo, the plan was to go out to dinner at a restaurant downtown in our gay community (Toronto), followed by a visit to a club that had a drag show and then back to their place for….???
Needless to say, the anticipation and preparation for the evening was almost as exciting as the evening itself. So many questions – some in my control (What to wear? What to bring? What time to start getting ready.. etc) and a lot out of my control (What if they look nothing like their pictures? What if they smell bad? What if it was all a big setup/hoax? What if they want to tie me up as soon as I walk in the room?). At the end of the day, I just convinced myself that ‘it was time’ – I could chose to stay alone in my femininity forever or take the leap..
So… the following are the specific details of the preparation and the actual night. There are 3 parts – I) the prep, II) the apartment and night out, and III) the return to the apartment. I will only publish parts I and II.. but will be selling part III on ebay to the highest bidder (just kidding)
Part I – the prep
Even though I thought I had a pretty decent wardrobe, there was a whole bunch of shopping for various things during the week to prepare. All done in 'drab', but I certainly pushed the envelope by trying on a couple of blouses at Winners (our equivalent of TJ Maxx) and also trying on boots and shoes at a local discount mall. I ended up buying a couple of new tops, a tight pair of woman’s jeans, a women's wallet, some nice 'chunky' jewellery, a pair of really sexy black boots, a spring jacket, and finally a MAC compact powder kit. This being a woman thing ain't cheap!!
My (x)SO left the house around 3pm in the afternoon so I could get ready - we had discussed the plans for 'the date’ in detail - and she surprisingly was quite supportive; her major fear was that the couple I was meeting could be psychos or something and I wouldn't ever be coming back home.. (Not sure if it was a fear or a hope..).
I had spent a large part of the morning preparing, a nice long relaxing shower, shaved my legs and all other non essential hair; applied lot’s of moisturizer; painted my toes. I had also packed a bag with my evening wear and a variety of ‘back to the apartment’ options. When my wife left the house, I did my 'day time' make-up, glued on my breast forms; got dressed in my tight new jeans and one of the new tops. The only issue was that I hadn't done my nail polish.. what a friggin’ nightmare it was trying to put that on while I was in a bit of a rush – lesson learned - next time I am going to plan to stop in a nail salon.. or just get some stick-ons.
Ended up leaving my house around 4:45, I was supposed to meet them at 5:30 at their place. Anyhow, pulled out the garage.. sans wig and earrings (just in case any neighbours happened to be milling about..) - no issues. Pulled in behind a warehouse and put on the wig and earrings - I looked fabulous (if I don't say so myself.. :o)
I had planned to make a few stops on the way there.. filled up the car, picked up some cash at a bank machine and picked up a bottle of wine at the liquor store. One little twist, as I was walking out of the liquor store, I passed by someone I know - she is a waitress at the bar we go to every Friday night after hockey; I am sure she did a double take when I walked by.. I just kept my cool and kept on walking. It will be interesting to see if she mentions anything.... I doubt it; maybe I will mention it to her…
Was running about a 1/2 hour late by this time.. definitely was feeling like a woman at this point! Anyhow, got to their place after a bit of a detour because of lousy directions from Google Maps. They live in a beautiful condo right on the waterfront (Lake Ontario) - had to check in with the security guard; I am sure he has seen everything under the sun - so no issues.. Make it up to the 6th floor and getting off the elevator, the only thought in my head was "I can't believe I am actually going to go through with this - last chance to turn around...". Anyhow - I made it to the door and knocked….
Part II to follow shortly.. but before part II; some things I would be interested in getting feedback on;
1) Has anyone gone this far with an ‘online’ relationship?
2) Normally I am a very ‘risk averse’ person – this was definitely pushing me way out of my comfort zone; was this taking too much risk?
3) Any other suggestions/comments on ways to meet ‘like minded’ cross dressers?
Warnings:
1) This is a long post…
2) This post deals with bisexuality; I understand and support the fact that a large percentage of this cross-dressing community define themselves as heterosexual. I therefore would ask that those who may be offended by this topic a) move on to the next thread or b) refrain from commenting in a negative way.
For those of you who have not read one of my previous posts (http://www.crossdressers.com/forums/showthread.php?t=95731) – due to my cross-dressing and a number of other contributing factors my SO and I agreed to separate sometime before Christmas. We are still living together, and overall the arrangement is ‘amicable’ – and quite honestly less stressful in a number of ways that it was before we decided to take this step; I no longer feel like I am walking around on egg shells – and there is no longer any ‘sexual’ tension between us either.
Since then, I have taken a number of steps to explore my femme side, this has included a few things like building up my feminine wardrobe – made some good progress, but that’s a job that never finishes, improving my femme appearance by getting more comfortable with putting on make-up, tweezing eyebrows, dropping a few more pounds and a few other little things. In addition to focusing on the physical aspects I have also been trying to find someone (anyone??) to a) go out ‘en femme’ with and b) explore/confirm my bisexuality. Well, I finally succeeded – on both fronts!!
Bit of a long story, but I joined one of those on-line dating sites catering to those of us who are interested in ‘non vanilla’ relationships. After numerous false starts and email exchanges I finally found ‘a couple’ that seemed to be just what I was looking for (and more!). When I say, “what I was looking for”, quite honestly – it was a no strings attached bisexual experience while cross dressed; I was/am still not looking to get into a long term relationship. In a nutshell, they are a couple where he is a bisexual cross-dresser and she is a very supportive bisexual GG. They have been in this relationship for several years and have had a number of ‘dates’ with other cross-dressers and also with some GG’s. It actually all happened quite quickly - after our initial email exchange, we chatted about ½ a dozen times to get to know each other better and to work out the details of our date; all of my communication was through the GG. Of course I was very nervous/leery about the whole thing – the list of things that ‘could go wrong’ was longer than the list of things that ‘could go right’ – but somehow I felt that this couple was genuine and not a psycho (or couple of psycho’s) setting me up for who knows what. The positive ‘clues’ for me were that our chats were not focused on sex – more general discussions really about getting to know each other; they did not want me to send pictures in compromising positions etc.. and also a big confidence builder was when she sent the address where they live and we were to meet – I knew it was a very good location; she also provided a cell phone number. The plan (after a few adjustments here and there) was for me to meet them at their condo – I was to be dressed casual ‘en femme’; we would have a drink and chat (or I could ‘bail’ right then and there before entering the apartment..), and then I would get dressed for the evening out and she would do my makeup for ‘going out on the town’ (did I mention that she also does make-up as a side job?) . After meeting at the condo, the plan was to go out to dinner at a restaurant downtown in our gay community (Toronto), followed by a visit to a club that had a drag show and then back to their place for….???
Needless to say, the anticipation and preparation for the evening was almost as exciting as the evening itself. So many questions – some in my control (What to wear? What to bring? What time to start getting ready.. etc) and a lot out of my control (What if they look nothing like their pictures? What if they smell bad? What if it was all a big setup/hoax? What if they want to tie me up as soon as I walk in the room?). At the end of the day, I just convinced myself that ‘it was time’ – I could chose to stay alone in my femininity forever or take the leap..
So… the following are the specific details of the preparation and the actual night. There are 3 parts – I) the prep, II) the apartment and night out, and III) the return to the apartment. I will only publish parts I and II.. but will be selling part III on ebay to the highest bidder (just kidding)
Part I – the prep
Even though I thought I had a pretty decent wardrobe, there was a whole bunch of shopping for various things during the week to prepare. All done in 'drab', but I certainly pushed the envelope by trying on a couple of blouses at Winners (our equivalent of TJ Maxx) and also trying on boots and shoes at a local discount mall. I ended up buying a couple of new tops, a tight pair of woman’s jeans, a women's wallet, some nice 'chunky' jewellery, a pair of really sexy black boots, a spring jacket, and finally a MAC compact powder kit. This being a woman thing ain't cheap!!
My (x)SO left the house around 3pm in the afternoon so I could get ready - we had discussed the plans for 'the date’ in detail - and she surprisingly was quite supportive; her major fear was that the couple I was meeting could be psychos or something and I wouldn't ever be coming back home.. (Not sure if it was a fear or a hope..).
I had spent a large part of the morning preparing, a nice long relaxing shower, shaved my legs and all other non essential hair; applied lot’s of moisturizer; painted my toes. I had also packed a bag with my evening wear and a variety of ‘back to the apartment’ options. When my wife left the house, I did my 'day time' make-up, glued on my breast forms; got dressed in my tight new jeans and one of the new tops. The only issue was that I hadn't done my nail polish.. what a friggin’ nightmare it was trying to put that on while I was in a bit of a rush – lesson learned - next time I am going to plan to stop in a nail salon.. or just get some stick-ons.
Ended up leaving my house around 4:45, I was supposed to meet them at 5:30 at their place. Anyhow, pulled out the garage.. sans wig and earrings (just in case any neighbours happened to be milling about..) - no issues. Pulled in behind a warehouse and put on the wig and earrings - I looked fabulous (if I don't say so myself.. :o)
I had planned to make a few stops on the way there.. filled up the car, picked up some cash at a bank machine and picked up a bottle of wine at the liquor store. One little twist, as I was walking out of the liquor store, I passed by someone I know - she is a waitress at the bar we go to every Friday night after hockey; I am sure she did a double take when I walked by.. I just kept my cool and kept on walking. It will be interesting to see if she mentions anything.... I doubt it; maybe I will mention it to her…
Was running about a 1/2 hour late by this time.. definitely was feeling like a woman at this point! Anyhow, got to their place after a bit of a detour because of lousy directions from Google Maps. They live in a beautiful condo right on the waterfront (Lake Ontario) - had to check in with the security guard; I am sure he has seen everything under the sun - so no issues.. Make it up to the 6th floor and getting off the elevator, the only thought in my head was "I can't believe I am actually going to go through with this - last chance to turn around...". Anyhow - I made it to the door and knocked….
Part II to follow shortly.. but before part II; some things I would be interested in getting feedback on;
1) Has anyone gone this far with an ‘online’ relationship?
2) Normally I am a very ‘risk averse’ person – this was definitely pushing me way out of my comfort zone; was this taking too much risk?
3) Any other suggestions/comments on ways to meet ‘like minded’ cross dressers?