#1366 - Sissy Story 44 - Life is such a blessing

Generally i receive a lot of messages every day.
maybe 30 or 40.. it depends.. anyway a lot..
excuse me, i'm not able to answer to everyone.. for a simple reason..
i have to think to write my daily posts.. and i have to live my real life also ;))
Anyway it's not common to receive a real letter like this, i have dediced to post today..
oh.. don't worry.. about your privacy..
i have obtained the permission.. and i will never post anything without it..
feel always free to write me.. i know what's mean to mantain a secret..
But this letter was more of a simply talk.. it was a true love story..
incredible, interesting, suffered, intense.. and i loved so much..
except the real names.. i have decided to post it.. integrally!
a big kiss to the sweetest sissy author.. ;))
enjoy the sissy story number 44!
with love

Anna Malice




Life is such a blessing


My name is Stephanie, or sometimes when I feel particularly naughty, Stevie. Although I was born and grew up as just Steve. I happened on your blog about two weeks ago and it has really sent me in a new direction but I’m getting ahead of myself. First, you’re free to post this but I wanted you to know a little about myself and why I feel your blog has made such an impact on me.
My father died when I was 4 leaving my mom and older sister to basically raise me. We grew up in a neighborhood where most of the boys were a great deal older than me leaving me to play mostly with my sister and her friends. There was one in particular, Kim that was just absolutely stunning even as a teenager. I was always trying to find ways to impress her but she didn’t seem very interested. While she was 4 years older, I was smitten even then.
One afternoon when I was 12, my sister Lauren and Kim were “dressing up.” Applying makeup, trying on my mom’s dresses and jewelry when I sauntered in. I was bored so I just sort of sat and watched when Kim suggested they do me. I wasn’t crazy about the idea of dressing up but anything Kim wanted to do was fine by me. At first Lauren said they shouldn’t but when I said I didn’t care she was okay with it “as long as we didn’t tell mom.” Actually I didn’t want anyone to know I was dressing up as a girl so she had nothing to worry about.
Kim told me to strip down and I remember I had on little fruit of the loom briefs. She said that wouldn’t do and got me a pair of my sister’s panties. I’m not sure who was more embarrassed me or my sister Lauren, but I turned my back to them and slipped off my white briefs and put on the panties to Kim’s whistles. As embarrassed as I was, I was secretly thrilled that Kim seemed to notice me now.
We spent the rest of the afternoon with the girls applying blush, lipstick, mascara and having me put on nighties and panties. Sadly that was the only occasion even though I saw Kim often at the house until she moved away two years later.
It was at college when I was 19 that I saw Kim again. While she had attended undergraduate at a girl’s school, she was getting her Master’s at State where I was attending. I nearly ran across campus when I saw her, and we hugged. I made plans to meet her at a local bar / restaurant that evening where we caught up.
Over the next few weeks we really spent time together with me finding every excuse to be at places where she went for food, drinks, or just between classes on campus. She raked them up to coincidence but I had carefully watched her and made sure to run into her. One night at her apartment off campus, we were having beers, and after one too many I tried to kiss her. Her demeanor changed immediately and after a few minutes she confided she was a lesbian.
I was crushed but she told me the story of how she was introduced to lesbian sex at the all female college and had simply never looked back. Although she liked me a lot, even though we had an age difference, she simply loved the touch and feel of a woman. As much as that hurt, we still saw a good bit of each other and sort of joked about how we had a great relationship if we could just get past the sex part. I knew she saw several different women on campus but there didn’t seem to be one woman she was stuck on.

Laughing about it one night, she said if only I was a woman. Then I reminded her what she and Lauren had done to me when I was 12. Kim said she’d actually forgotten about that. It was actually as if a light went off when she sprang up and came back with panties and a bra. Kim looked me in the eyes and told me to put them on.
I looked at her for several seconds before I gathered she was not kidding. When I asked if she was going to turn around she asked why, was I modest?
Here I was, with the woman I had loved since I was 12, and now for the first time she would see me naked. I slid off my jeans and briefs (No not Fruit of the Loom whities) and put on the bra and panties. Kim stared at me for several minutes or at least it seemed like that before she asked me to walk over. She had me kneel where she leaned in and kissed me. A long, lingering, soulful kiss. It was what I had wanted for years.
She began disrobing having me kiss and suck her breasts which I fell in love with before she removed her shorts and panties and had me go down on her. Her pussy was absolute heaven and I knew I would stay between her legs forever if she would let me.
Before the evening was over, she rubbed my cock under my satin panties as she kissed me. I actually came in her panties! After that night, we got together even more frequently but each time she dressed me in panties and a bra and would do my makeup, making me look more and more like a girl. Actually I looked really good I thought. I was never very hairy and she had me shave off what little hair I had on my legs, underarms, and crotch around my cock and balls. I have no hair on my chest at all anyway.
She had one female lover Beth that came over sometimes while I was there and they often excused themselves to go to the bedroom. Kim said she didn’t want to hurt me by making love to another woman in front of me but I told her I understood. After that, it was out in the open, and I often watched as Beth embraced her and sometimes took her in front of me. They both seemed to enjoy having me watch.
I had been embarrassed at first dressing in panties and bra in front of Beth and being “Stephanie” but in little time I became very comfortable with her, allowing Beth to fix me up when Kim wasn’t there.
After Beth graduated, it left Kim mostly to me. Sex with Kim had been her using dildos and vibrators on me as I jacked off. Often Kim would suck my nipples which were pretty sensitive but she never ever went down on me and rarely ever touched my cock which she referred to as my little clitty.
One night we moved to her fucking me with a strapon which I actually enjoyed. She would have me dress up and then she'd take down my panties and make me suck her cock before she had me lay on my back, spread my legs, so she could fuck my pussy. I would pull on my clitty as she sucked on my nipples or kissed me. It was the most amazing sex I’d ever had and I loved her.
I can't tell you how many times I begged her to marry me but she reminded me while she loved me, and she had stopped thinking of me as a guy, she still needed to have sex with other women…. And after all, while she didn’t think of me as a man, I was after all still a guy.
It was about six months ago that Kim sat me down at a computer and had me watch porn clips of she males and transexuals on websites. I had never paid that much attention to Transsexuals before, but I had to admit, I was intrigued. After all, I had been cross dressing for more than 2 years on campus. Often wearing panties and a bra with painted toenails under my sneakers, jeans, and sweat shirts. Kim had long ago tossed all my old men’s briefs and boxers and when I was home it was always straight to my bra and panties.
Kim asked if I’d ever consider perhaps going further. Actually transitioning from a man and while not quite a woman, a she-male. With hormone treatment, therapy, and a little work, much of my masculine appearance (what was left) could be altered and I could be the woman both of us wanted.
I thought about it for a few weeks before I told her one night I would do it. Kim reminded me once done, it couldn’t be undone. While I did not have to remove my cock and balls and be completely feminized, once I started on the hormone treatment, the breasts and other features would remain with me. I told Kim I wanted her more than anything in my life and I wanted to do this for her. Anyway, I had pretty much been living secretly as a female for 2 years or more and was totally comfortable with it. I wasn’t sure I could go back anyway.
We met with a therapist who explained the procedure and the impact such a decision has on your life. I had already felt the sting of that in the job I had taken after graduating with some of the coworkers who made comments on the way I acted and looked. I took a position at a female owned marketing firm as the concept designer. Margie spied toe polish when I had slipped my shoes off at my desk.
I guess it wasn’t a far leap anyway and she indicated she had suspected I cross dressed by the bulky nature and sometimes tell-tale lines under my shirt. Margie was very supportive as was the rest of her all female staff and often encouraged me to wear female slacks and shirts if it made me comfortable.
I began the hormone therapy about 12 weeks ago with a pill I was told to take every day and don’t miss one. Also shots in my fanny which hurt as I hate needles. Needles was something I had to get used to as the next thing was electrolysis to remove facial hair and Kim went ahead and head the hair on my crotch removed as well (although I still shave my legs and underarms).
I have noticed my breasts swelling just a bit and my nipples are larger, puffy, and sore. I also have noted that weight has shifted to my hips and ass and I’ve lost some muscle tone. I was given a nipple suction cup much like mother’s use during lactation to expand my nipples and give them form.
I was beyond excited when the doctor marveled at my progress and told me given my young age in the decision, I should grow very nice size B breasts. He did comment that my testes would shrink leaving me sterile but not altogether impotent if we didn’t over do it on the meds. Kim said she actually didn’t care about my penis and balls as they were useless to us both and really was just a reminder of what I used to be.
Kim finally accepted my proposal and said she would love to marry me, sometime next June. We would have the formal civil ceremony and then another where I was actually dressed as the June bride. She hoped by then my breasts will have formed more and I should be far along in my transition. We've even looked at several dresses for me!
It was Kim who first broke the news about my transistion to Lauren who was initally upset. She felt guilty that what they had done years ago with me may have resulted in this until I convinced her how happy I was. Mom on the other hand was not receptive and it was some time before we could openly talk although she has refused to take part in either wedding ceremony and places blame on Kim "for what she has done to me."
While I do not fuck Kim with my clitty (tiny penis), she allows me to strap on a cock – a nice seven inch one and much bigger than I used to be – and fuck her pussy. I often cum that way as she sucks my nipples with the leather moving back and forth on my clit.
It was two weeks ago though that things sort of changed for me Anna. I found your website with the sissy training and all of the cocks. I have never, ever been interested in cocks before. Even growing up going to school, I could care less what size penis another boy had. But here I was staring at all the dicks, watching the she males and sissies suck them. Letting them fuck them in their "pussies".
One night I was already in bed and I started to cry. I was really eaten up emotionally. I had never just cried before but Kim comforted me telling me it was the hormones. To not be concerned with showing emotions, it was all part of the therapy. I then explained what I saw and how it made me feel with the men and their cocks. Kim actually laughed and told me that was natural too. While she wasn’t interested in men’s penis’s herself, it was only natural for a woman to be. She told me congratulations, I was certainly a woman with feelings a woman has. She told me I should embrace those feelings and just as she likes to have occasional sex with another woman, which I not only accepted, but encouraged, I should have sex with men when I have the impulse.
Kim informed me she knew a guy who was gay and would love to make love with a young she-male. We lay in bed that night with her kissing me, caressing and holding me, telling me how exciting it would be to watch me suck on a real male cock and be taken like a woman in my pussy.
The guy is Ben and he is coming over next weekend. I am so excited! Again, I may never have taken this step if not for the videos on your blog. I can only imagine the number of guys out there who only fantasize about being a she male. Looking in the mirror tonight, I am so happy with who I am and what I have done and I can’t wait till next year to marry my long time partner. Life is such a blessing! And thank you for your amazing blog!

Stevie