A first time for everything!

[stlpenguin]

Hey everyone!

A lot of new things have been happenning for me recently, and I kinda wanted to keep a journal of all the stuff going on and new sexual doors opening to me. I figured since a great amount of it has to do with my crossdressing - and apparently now sexual encounters with another man - I'd keep that here, so you can all share in the experience.

So, to start : For those of you who don't know me yet, my name is Scott, and I'm a submissive crossdressing male. I'd classify as "straight" but only because I'm not generally attracted to men. Recently, though, I've had sexual exchanges with a man, so I'm not really sure where that puts me. "Straight, but willing" I suppose works. Who likes labels anyway?

I've been crossdressing in minor ways for years - I have a huge nylon fetish, and liked wearing them from time to time... I always just thought it was part of loving nylons, and never ascribed it to any sort of crossdressing. Over the years, though, I found my desire to try other clothes picked up. Along with my distaste for masculine qualities in general (beer / sex / sports) and my reverence for the more feminine qualities, my crossdressing picked up quite a bit of steam.

However, about the time that I was really giving serious fantasy time to entertaining my feminine side, I was getting married to my wonderful wife. I was petrified of admitting any of my deep desires to her - to dress and feel like a woman, and be treated like a woman in the bedroom... taken from behind and penitrated, etc. As it turns out, all my worry was for nothing, as about a year ago, we had a nice long talk, and all of this came out. She wasn't very surprised, and told me she had known for a while, but was waiting for ME to admit it to MYSELF.... that if I wasn't comfortable talking to her about it, she couldn't change that, and I had to come to terms with it first. She was right, of course, and having that off my chest feels great.

I endulged my crossdressing for a while, buying a wig and some wonderful fake breasts (cute little B/C cups!) and my wife even took me out shopping a couple of times so I would stop raiding her clothes. But in the bedroom, things failed to progress. She payed lip-service to my desires beyond just dressing, but something was missing. Shortly after, we realized what our problem was :

We're both submissives. BIGTIME submissives. I wanted her to take charge, and mentally, she just couldn't. Likewise, I felt unable to switch for HER to fulfil her needs. My wife used to submit to a Domme friend of hers, and that's how she got involved in the BDSM lifestyle. I was new to all of it - consequently, she knew what she was looking for, but I didn't. After some talking, we decided that both of us seeing a Dom/me(s) was going to be the best solution for us.

I ventured out on Collarme.com, and these boards, and some local BDSM communities here in the Detroit area. All seemed for naught - we didn't seem to have the budget for more than an hour / month for a pro Domme, ($200 / hour, ouch!) and paying for the sort of thing I was looking for just felt like prostitution... and being a romantic at heart, I didn't want payed-for affection.

Meanwhile, as I was failing to find anyone, my wife learned that a friend of ours was Dom, and had recently gotten married to a wonderful woman and was living about 40 minutes away from us. Feeling comfortable with him, and knowing that both he and his wife were very open, accepting, and affectionate people, asked permission to be Dominated by Him. He accepted, and my wife was happy! Sir's wife was a little timid, being new to the whole thing - not unaccepting, but perhaps a little overwhealmed. She very much liked to watch, though, and occasionally touch herself and my wife during their sessions.

I was failing to find anyone right for me... so out of curiosity, I asked my wife if it would be cool to come and hang out during one of their sessions. It was instantly agreed on by all involved parties, and we had a very nice evening - home-cooked dinner, a movie, and then clothes started coming off. Sir thought it was a good idea that I not just spectate that evening, and instructed his sub (my wife) to take my pants off and suck me off while everyone watched. It was a HOT evening, and I was thrown into the fire very quickly by them... and I loved every minute of it.

Sir's wife and I began talking regularly, being the two odd-ones-out in their Dom/sub relationship. At one point, (that pivital moment where everything changed) I made some smart-ass remark to her, purely in jest, and she grabbed the back of my head by my hair and demanded I appologize - she wasn't truly mad, but we both realized two things : I was looking for a Domme, and she was quickly finding out she loved being Dominant. It was a match made in heaven. My wife with her Husband, and now Ma'am with me! We could all four be together, keep communication open and transparent, cater to one another's desires, and continue being great friends outside of our respective roles!

So, Ma'am and I talked, and I told her all about my crossdressing, and how it played into my being a submissive. Her eyes lit up, and she told me she wanted to see me "en femme". I came over the next night with my little plaid jumper, wig, makeup, and these CUTE thigh-high stockings with little white bows on the bands. Top those off with these great black 4" heals I've got, and I nearly knocked her socks off! Ma'am is bi, and loves seeing me as a woman as much as she does a man! She treated me like a woman, and told me how she couldn't wait to penetrate my little ass. Again - match made in heaven!

(CONTINUED)

 

[stlpenguin]

Ma'am and I played around quite a bit over the next few weeks, until one night, we decided to go out for a fun Saturday evening (Cinco de Mayo) at the local gay/TG club renouned as THE place for crossdressers. I spent the evening getting all dolled up in a cute little silky blue dress with an oriental white floral pattern in it, and red trim along the deep V-neck / back and empress waist. White nylons, little strappy 1" baby heals, and a yellow flower berret in my hair, and I was ready to go!

We got to the club okay, and had the time of our lives! This was the third or fourth time I had gone out in public dressed, but it was the first time men had bought me drinks and flirted with me! Gay, straight... it didn't matter. One way or another, it felt wonderful to feel appreciated by a stranger - especially feeling as vulnerable as I did dressed up like that. So, mark that a successful night out with Ma'am all dolled up and playing the roll of Sara!

That night, I told her that I was feeling very comfortable with everything... and then when I was dressed, I felt a lot more like a woman, and had more womanly desires - and that included men. If She wanted, and if Her husband was okay, I wouldn't mind fooling around a bit with him. She was delighted at the idea of seeing me servicing Her husband!

So, the next night, I came over and Sir had my wife dangling from the rafters of their basement in bondage and a blindfold as he smacked her with a leather flogger. Ma'am was looking stunning, and after greeting me warmly, walked me over to Sir and instructed me to get down on my knees before him, and take him into my mouth. I was a little timid - this would be my first sexual experience with a man - but I sucked him hard, but not to completion. Ma'am was disappointed that I didn't finish, but understood that it might be a little much for me all at once, so didn't press the issue.

That evening, things progressed wonderfully, and all 4 of us were playing together. I was sitting in a chair in their livingroom, and Ma'am was cuddled up on my lap, kneeling in front of me with her arms around my waist. Sir came up behind her, and took her right there. It was incredibly hot watching Ma'am be fucked by Sir righ on top of me, and I became hard very quickly. Sir was delighted by this, and reached forward and grasped my cock in his big gentle hand, and began to stroke me off. It felt amazing, and I laid back and let it all wash over me. I exploded like a fire hose, coming all over everything! (Quite an embarasing mess, honestly) And that marked my first time fooling around with a man. I never had any regrets or second thoughts about it (like I thought I would - I always counted myself straight but curious, and I've often heard that fantasy seldom lives up to reality. I'm glad I was wrong!)

 

[stlpenguin]

Two nights ago, I went over to Ma'am and Sir's to cook them dinner. Apparently, my wife had let slip that I make a respectable stir fry, and they wanted me to prove it After dinner, we put in "Victor / Victoria" and watched that - an enjoyable movie, but maybe only once. Plenty of homosexuality and gender-bending, and an all-around fun time with great dialogue. Cute, but not a multi-watcher, I don' think.

Sir was falling asleep by the end of the movie, so Ma'am and I wanted to move Him to the bedroom and put him to bed for the evening. Neither of us had intentions of playing when we went into the bedroom, but as we were laying Sir down, He pulled me down onto the bed with him, and threw his arms around me to cuddle. I was wearing a pair of black pantyhose under my pants, and Sir loves nylon almost as much as I do! So Ma'am laid down next to me, and made a me-sammich on the bed. I was in bliss. Touching and kissing progressed, and Sir was fondling my cock through my pantyhose, and then inside of them. To make things easier for him, I pulled them down a bit, and he began jerking me off in ernest. Ma'am was loving the visual, and sat back more to watch us.

She told me, "Shhh. Just lay back and enjoy." To which I replied, "I kinda feel like touching back, though." Ma'am and Sir were more than willing to oblige. I reached down, and began returning the favor to Sir.

I felt like a change of position was necessary, since the angle from which I was touching his cock was a bit ackward for me - and I figure, any job worth doing is worth doing right. I knelt beside him and stroked, and he to me. After a minute, I gathered up the guts, and went down on him again... this time working him vigorously, and taking his whole dick into my mouth. I tried everything I knew to please him, even taking breaks and using my saliva as lube to jerk him off by hand with. It didn't take too long (and I was enjoying it all the same, even if it DID take long) before he began to groan to let me know he was about to cum. I plunged his dick deep into my mouth and swallowed ever drop he spurted. I wiped my lips slightly, and smiled at them. Ma'am looked like she was going to cum just from watching!

So, that was two nights ago... I'd love to hear other people's thoughts, feelings, comentary, etc on the subject. I'll even see about posting some pictures of me all dolled up for you guys and girls! I'm feeling better than I ever have about who I am, and about my sexuality, and I want to share with all of you here at Lit who tollerated my lurking on your boards for moral support and advice as I became more comfortable with me.

I'll be posting more as more things happen. If nothing else, I'll have some hot stories to tell

-- Scott / Sara

 

[omniavincet]

Hey Scott, it's great to hear about your experiences. If I could make my dream scenario happen it would look a lot like yours. It's also kind of eerie how similar our circumstances are - married, crossdressing inclinations, etc . Glad to meet you - look forward to hearing more.

OV

 

[Night_Jasmine]

It's great to see that you and your wife as well as your Dom/Domme are doing so well. I'm submissive but not to the whole get off on pain type of thing, not that I've tried it though.

When I was married (Before discovering I was lesbian), I kept trying to get my husband to take control but it was always the same thing over and over again. Vanilla is ok but not as a steady diet.

Maybe one day I'll find a lady who will make love to me but also has no fears of taking charge when the mood strikes.

 

[stlpenguin]

So, the other night, I got myself all showered and shaved (everything - I only have hair on my head) and that got me feeling all sexy and feminine... so on a whim, I decided I was going out to the Rainbow Room. I hadn't been out and dressed since Cinco De Mayo, and wanted to get out of the house for a bit.

I called up Ma'am. Sir FINALLY had a night off from his midnights job, so I told Her what I was planning, and asked if Her and Sir would like to come with me. Sir had been wanting to for a while, but just hadn't had the time or inclination. Sir said He wasn't feeling well, and wanted just a quiet evening to vedge on the couch.

I somehow got into my littlep plaid jumper, with some white tights and my cute black heels, and came over. When I got there, Ma'am and I evicted Sir from the couch, stripped him down, and forced him to get clothes on to go out with us. He put up a small fight, but we won over in the end!

With Sir in jeans and a nice black shirt, and Ma'am with Her "sexy librarian" look going on (and dear goddess is it hot!) in a long patterned skirt, a velvety black top, and her strappy heels, we were ready to go.

The club doesn't have a very large crossdressing crowd, but I've never been treated with anything other than courtesy there. We got a table, and more or less sat around drinking and talking the night away. Half way through the night, we met a cute guy who was just kinda staning around by himself - we invited him over, and we talked to him for the rest of the night. He was really nice, bi-curious, and just out after work for a relaxing evening but too timid to go talk to people. He'd never been with another guy before, but was kinda 'in the market.'

We took him back to Sir and Ma'am's place after we were done at the bar, and sat in the living room talking about everything until about 3:30 in the morning. People were falling asleep, so we all left. It was just a great evening all around, and it felt soooooooo good to be out in public all dressed again.

I know I promised pictures, but my digital camera's batteries were dead.

I'll see if Ma'am has any pictures I might be able to post.

-- Scott / Sara

 

[stlpenguin]

Two experiences to share today, each happened last weekend.

First was a little bit of playtime with Ma'am that got Sir involved. Ma'am had ordered me to please her, so I was going down on her and making Her squirm. She was having a wonderful time, and began telling me how much She wanted my hard cock inside of Her. Well, one of the rules my wife and I have with our Dom/mes is no actual intercourse. Everything else is fair game, but we want to keep that one thing sacred to us. So, my suggestion was, if she wanted a hard cock inside her, that I go ask Sir to join us so She could get the fucking She needed. She readily agreed.

So did Sir.

Sir's knee was injured, so it was uncomfortable for him to be suppored by it, so he lay on his side behind Ma'am and did Her that way. It was also wonderful for me, because I could see everything clearly then, and could have a little fun of my own. I leaned my head in, and began running my tongue over clit and balls alike! We changed it up a bit - me pinching Ma'am's nipples, Her sucking on my cock so she could feel the pleasure of two men inside her... then Ma'am began telling Sir that She wanted ME to make him come, and to pull out and let me work on him. He obliged, and I hungrilly began sucking his cock. Ma'am begged me to make her come at the same time - I was being ordered to give a simultanious orgasm! I wasn't sure I was up to the job! I tried anyway, and it went surprisingly well - I sucked Sir with my mouth and stroked him with my right hand, while furiously working Ma'am with two fingers of my left hand. It was the most multi-tasking I've ever done in a bedroom! And it payed off, too, because just as Sir began groaning and spurting his load into my mouth, Ma'am began crying out her passion as she came also! It was severely hot, and everyone was happy in the end.

The next night, Ma'am and I got all dressed up and went out to the Rainbow Room in Detroit. We had a great time just drinking and talking - I'm getting to know the other crossdressers that frequent there. They're a great bunch of people. We all sat at one table like a mini-tranny convention. I was even feeling confident enough to go up and sing some karaoke! (I tried Milk by Garbage, but it was some weird remix and was nothing like the album version, so I did poorly) We even called Matt, the cute guy we met last time, and told him to come have a beer with us. All in all, it was a great time with good friends!

Here are some pictures of me before we went out - Finally!

-- Scott / Sara

 

[Night_Jasmine]

I like the pictures! Really cute little outfit!

 

[MyFriend27]

Pics?

They are horrible. I hate to sound like Simon Cowell but that dress is atrocious. You have no freakin sense of style

 

[Riley_James]

Don't Listen

Sara/ Scott honey,

Don't listen to that nonsense. You are beautiful and sweet and charming.
You look wonderful.

Hugs,
Riley

 

[long_haired_lad]

They are horrible. I hate to sound like Simon Cowell but that dress is atrocious. You have no freakin sense of style

Do you have to be such a total cunt?

 

[stlpenguin]

It's fine. MyFriend27 is entitled to his/her opinion. That's the first complaint I've ever had on that dress. *shrug* I also never claimed to be a fashion model.

This weekend was a blast. I'll have pictures to share from that a little later, hopefully... I spent the entire weekend with Ma'am and Sir. We did all sorts of great stuff. Friday night was mostly playing around, just the three of us. My wife also came over that evening, and we enjoyed the evening together pleasantly.

Saturday was an absolute hoot. I made cheese omlets for everyone, and then Ma'am and I went downtown to go shopping at the thrift store. (Neither of us are particularly rolling in money...) I picked up a handful of really nice skirts and a top or two, and Ma'am got to really nice dresses. I decided we needed shoes, so we drove to the nearest DSW store, and got the sexiest red pair of heels I've ever seen!! (again, pics to follow) The best part, was they were $12. They're slightly trashy, but hey, who gives a fuck sometimes, eh? Armed with new clothes and some new makeup, we geared up to go out to the local TG friendly club, Gigi's. Saturday nights are drag queen nights, and the crossdressing crowd outnumbers those actually representing their own gender. It's a BLAST. Ma'am, Sir, and I did our fair share of people-watching, drinking, and listening to the music... none of us were much in the mood for dancing, and the fact that the absolutely GORGEOUS boy kept coming by with little $1 shots helped keep us (me, at least) glued to my seat. About 1ish, we decided to call it a night, and went back to Ma'am and Sir's where the real fun began.

Ma'am had me change into something a bit more ... comfortable. Black stockings, garter belt, black neglegé, and black opera gloves. Ma'am had me bent over and begging to be penetrated. It was a great time, with fingers and dildos, but unfortunately I'm a bit out of practice, and it was beginning to hurt before it went too terribly far. Sadly, I had to ask her to stop. While it lasted, though, it was a TON of fun.

The next morning I made french toast, then it was off to downtown Ferndale, MI for Motor City Pridefest! Michigan's largest GLBT Pride Festival! I was dressed in a cute little blue top, a dark blue skirt with a white floral pattern on it (that's just the most comfortable skirt ever made.) beige nylons, and my little 1" baby heals. We walked downtown, and spent the next 6 hours shopping and talking and collecting literature. Affirmations - a wonderful GLBT support center - was having its grand openning Sunday, so we got to take a guided tour with the absolute CROWD of people that were there. It was great, and I hope to be attending the TG Support group that goes on every Tuesday night.

Most of all, though, it was the first time I was in general public dressed up. I didn't have the wig and the makeup or anything... just a skirt, nylons, and heels... well, okay, a rather girly top too. But still... Ma'am has been such a huge source of strength and encouragement for me. With her by my side, I never flinched once, walking into public dressed as I was, bright red nail polish and all. Thanks again, Ma'am, for a great day!!

At Affirmations, they have a borrowing library. I picked up a copy of My Husband, Betty by Helen Boyd. I've only read the first chapter so far, but it's got to be one of the greatest, most accurate books about crossdressing EVER. The best part is that it's not written for the crossdresser, necessarily, but for their significant other, to help them better understand what goes on in their husband / boyfriend's head. I'd suggest the book to everyone who is either in a relationship with a crossdresser, or a crossdresser themselves.

Thank you everyone for your support! I'll keep posting here as I have new adventures to share with you all.

-- Scott / Sara

 

[CoastalTom]

Do you have to be such a total cunt?

No kidding. Get a thread and waste your time somewhere else...

 

[stlpenguin]

Well, I went to the Transgender support group at Affirmations, and it was great! What a wonderful bunch of people, who were all very encouraging. I didn't quite know what to expect - as it was a "Transgender" group, and I'm still a bit confused as to how a mildly dysphoric crossdresser fits into that - so I went as Scott. I brought Ma'am along, as she's a great source of strength for me. It seems to me that they all knew my story before I opened my mouth... apparently, the crossdresser who gets his first addicting taste of walking the other side of the gender line on Halloween is a regular tale. Next Tuesday, they're all looking forward to meeting Sara.

I'm about half way through My Husband Betty. It's been a really really informative book so far. Its helped me understand a lot clearer the problems my wife may be experiencing with my crossdressing, so I can better accomodate her and help ease some of the tension between us. Once again, to any other crossdressers out there, I can't suggest it enough.

-- Scott / Sara

 

[long_haired_lad]

Well, I went to the Transgender support group at Affirmations, and it was great! What a wonderful bunch of people, who were all very encouraging. I didn't quite know what to expect - as it was a "Transgender" group, and I'm still a bit confused as to how a mildly dysphoric crossdresser fits into that - so I went as Scott. I brought Ma'am along, as she's a great source of strength for me. It seems to me that they all knew my story before I opened my mouth... apparently, the crossdresser who gets his first addicting taste of walking the other side of the gender line on Halloween is a regular tale. Next Tuesday, they're all looking forward to meeting Sara.

I'm about half way through My Husband Betty. It's been a really really informative book so far. Its helped me understand a lot clearer the problems my wife may be experiencing with my crossdressing, so I can better accomodate her and help ease some of the tension between us. Once again, to any other crossdressers out there, I can't suggest it enough.

-- Scott / Sara

I'm glad things are working out for you.

 

[pagangrrl34]

Hi All

Know it's been a while since he posted, hopefully he'll have something to post about soon. Between other committments (wedding anniversary, ten days in the woods) and his computer graphics card taking a nosedive.............

So, yeah, Scott/Sara? Post something soon! Sheesh!

~Ma'am

 

[GentleSub_Ivy]

Scott/Sara,

Thank you or sharing your experiences. I'm in Michigan so I appreciate the references you are making to the area. Not that I'm brave enough to check places out yet but you do give me inspiration. I'm glad things are going so wonderfully for you.

Ivy

 

[stlpenguin]

Very soon. I've got some wonderful things to post here about recent experiences, but I haven't the time. I promise, in the next day or two!!

-- Scott / Sara

 

[Bicuriousone]

Cute Pictures

Two experiences to share today, each happened last weekend.

First was a little bit of playtime with Ma'am that got Sir involved. Ma'am had ordered me to please her, so I was going down on her and making Her squirm. She was having a wonderful time, and began telling me how much She wanted my hard cock inside of Her. Well, one of the rules my wife and I have with our Dom/mes is no actual intercourse. Everything else is fair game, but we want to keep that one thing sacred to us. So, my suggestion was, if she wanted a hard cock inside her, that I go ask Sir to join us so She could get the fucking She needed. She readily agreed.

So did Sir.

Sir's knee was injured, so it was uncomfortable for him to be suppored by it, so he lay on his side behind Ma'am and did Her that way. It was also wonderful for me, because I could see everything clearly then, and could have a little fun of my own. I leaned my head in, and began running my tongue over clit and balls alike! We changed it up a bit - me pinching Ma'am's nipples, Her sucking on my cock so she could feel the pleasure of two men inside her... then Ma'am began telling Sir that She wanted ME to make him come, and to pull out and let me work on him. He obliged, and I hungrilly began sucking his cock. Ma'am begged me to make her come at the same time - I was being ordered to give a simultanious orgasm! I wasn't sure I was up to the job! I tried anyway, and it went surprisingly well - I sucked Sir with my mouth and stroked him with my right hand, while furiously working Ma'am with two fingers of my left hand. It was the most multi-tasking I've ever done in a bedroom! And it payed off, too, because just as Sir began groaning and spurting his load into my mouth, Ma'am began crying out her passion as she came also! It was severely hot, and everyone was happy in the end.

The next night, Ma'am and I got all dressed up and went out to the Rainbow Room in Detroit. We had a great time just drinking and talking - I'm getting to know the other crossdressers that frequent there. They're a great bunch of people. We all sat at one table like a mini-tranny convention. I was even feeling confident enough to go up and sing some karaoke! (I tried Milk by Garbage, but it was some weird remix and was nothing like the album version, so I did poorly) We even called Matt, the cute guy we met last time, and told him to come have a beer with us. All in all, it was a great time with good friends!

Here are some pictures of me before we went out - Finally!

-- Scott / Sara

These are cute pictures but sure would love to see some of you without the dress on or some of you in action.

 

[cowboy_choji]

Nice pictures, you look very cute especially in the second one.