Boyfriend?

So, I one of the two guys I sucked recently asked me to get together again.   I could not host at home, nor could he, so, I met him in a parking lot.  I got partially dressed and slipped out of the house, finishing my makeup and putting on my cute WH/BM skirt.  I then drove to the parking lot, purposely parking a few cars away from him.  I stepped out of the car, slipped my purse onto my shoulder and walked across the parking lot to the car.  It was very exhilarating. I opened the car door and slipped into his car, being careful to keep my knees closed and smoothing my skirt underneath.  How fem.  We drove off and soon his hand was between my legs!  Mmmm.  He then un-did his pants and lowered them.  I leaned over and began to lick his pretty cock.  Soon I was kneeling on the floor and going at it like there was no tomorrow!  Eventually, he found a secluded spot and stopped the car.  He then proceeded to face-fuck me.  He held my head as he thrust all the way in.  I gagged a bit but eventually got used to it.  Mmmm.  My mascara did run a bit though.  So, I wanted him to cum in my mouth so I used a combination of my hand and mouth to get him really going.  I could sense that he was close by the grunts and moans.  He came in my mouth and I swallowed without my  really realizing it.  Damn.  So, we drove off, and as we did, I  lowered the visor mirror, checked my makeup.  My eyes were a mess, looking like some slut that had just sucked off a guy.  Giggle.  I then opened my purse and took out my lipstick and reapplied it.  Mmmm, so girly.  He dropped me off at my car and I took a quick stroll around to get that sexy walking in heels feeling.  A lady was getting into her car and noticed me but did not seem to get that I was a sissy.  Hehe.  I must be getting good. 

So, apparently he does not like the girdle that I use to hold up my stockings.  He wants to get me a pretty thong.  I told him that I would need a garter belt then.  I so hope that he does!  I am thinking that I will require a present each time I suck cock from what I think could be a group of "regulars".  Perfume, lingerie, clothes...I may have a new profession!

Update

Hi All,

I have not posted for a while.  Sorry. 

So, I deleted a number of posts that dealt with my being a counter girl for a major cosmetics company.  I was enjoying myself so much that I did not want someone in the organization to recognize me and call me on it.  Again, sorry. 

So, I am getting better and better at applying makeup.  My briefcase is essentially a large purse now and I always have some makeup on.  I am starting to feel like it is actually a part of me.  And I feel so sissy with a makeup bag always at my fingertips. 

In other areas, I have sucked off and fucked two more men.  They seem to love me as they want to get together again as soon as possible.  I really need to try two things still. Having a man cum in my mouth and having a man shoot on my pretty sissy face.  I am sure that these will happen soon.  I also want to fluff a guy and then perform clean-up duty on the lady.  It is so sissy! 

Thanks for listening and feel free to comment or ask questions! 

Love, Diane

My Perspective Today

I have been pondering my present status.  I clearly have one foot out of the closet.  I am totally scared of showing my true self to friends and family.  But I am out to many, many people now.  I suppose that it is a matter of time before someone who knows compares notes with one of my friends or coworkers.  I am not sure what I will do at that point but I shall not worry about it now.  I will probably play it based on the reaction of the friend....

In any case, I coined the expression "anonymously out" to describe my present state.  I have now bought clothes in many stores, having tried them on with the sales clerk's assistance.  I buy makeup while wearing makeup.  I wear women's clothes when I get my hair and nails done.  I wore a women's suit, stockings and flats to a bar and had a drink.  I frequently wear jewelry while running errands.  So, there are probably well over 100 people who know that I am a sissy.  The world has not crashed down on me!  Not one of the persons listed above has said anything to suggest that they disapprove of my sissiness.  Wow. 

So, I am not sure where I shall go from here. 

I did it! More thoughts!

So, as you might be able to tell, I had sucked a cock and been fucked.  And even kissed a guy.  Wow.  I am now a complete sissy.  I placed an ad on Craig's List and picked amongst the candidates.   He arrive to find me wearing my grey sweater dress.  I wasted no time in getting on my knees and opening his pants.   He was soft but after some effort on my part, he hardened.  I am proud to say that I managed to take him all the way in.  It was so much fun but he did not cum.  I was amazed at his manly smell and enjoyed the pre-cum as it came out but I was disappointed that I did not get a sudden explosion to the back of my throat.  In any case, I asked him if he would fuck me.  He bent me over the couch and proceeded to slide it in.  I loved it!  He pumped me nice and hard, as I wiggled my sweet ass to meet his thrusts.  I could tell when he came by the way he was breathing and the fast pace of the fucking but I did not feel the cum.  Another disappointment.  I did enjoy as he slowly slipped out of my ass and I turned and gave him a big kiss!  He has asked for a return engagement, hehe...we'll see. 

I am seriously considering a second act tonight....

Post Coital Reflection

Wow!  I am still shocked. 

So, I started today by making an appointment to get my eyebrows waxed.  I planned on getting them done after work but decided to leave work early to get dressed a little.  I Came home and fussed over outfits, finally choosing my black suit.  I wore a white button down blouse that could have been a shirt with a white cami below.  I wore black knee highs and my black ankle shoes. Not overly obvious but clearly sissy to anyone who actually looked.  I put on a light foundation and light mascara and headed to the appointment.  None of the ladies at the salon looked shocked or asked about my style...damn.  The beautician did ask if I wanted a "defined arch" though.  She absolutely knew...of course, my cami was probably showing and my knee highs were right out there.  So, she did a very nice job, waxing, plucking and trimming.  Very definitely girly eyebrows. 

It only took a minute or two and I was out the door.   Now what to do.  There is a bar across the way and I went in.  I sat at the far end of the bar, near where the waitresses picked up their orders.  The bartender was a sweet young lady too.  I think they were aware of my situation but none of them said anything.   I was so hoping to engage with the bartender, at least....oh well. 

Meanwhile, I had posted a personal ad on Craigs List....could I go through with it this time.  I received a number of replies but finally went for it, giving my address to a guy that was going to be in the neighborhood...I rushed home to get dressed and put on my makeup.  I was going to actually do it!!!! 

And, I did!

A New Year!

So, I started off the new year with a nice chat with Kirstie at Nite Flirt. We chatted a long time about me losing my virginity.  So, I am once again seriously pondering the idea.  I also tried something new.  One of the things that would be cool is being bent over and fucked, panties down at my ankles and dress over my head.  When he's done, pulling up my panties and putting my dress down.  And then feel the cum oozing from my hole.  So, today, after I came, I put the cum in my ass and I am sitting here waiting for it to leak out, into my panties.  I am not sure how long it will take but I will let you know how it goes.