Cuming Out to My Girlfriend

Preface: This story is partially autobiographical. The way that my girlfriend learned of my wanting to be a girl is 100% true. Everything that's happening in the present, in the story, is fiction. In reality, my girlfriend of 5 years left me a couple of months after the incident happened and I'm still looking for a dom mistress to control me into feminine submission. If you like my story, feel free to drop me an E-mail to say so. Or, if you're a dom who wants to take over my training, please let me know. Kisses. Jessica.



As I stepped onto the bathroom scale, and looked down at the digital numbers displayed, I couldn't believe what I was seeing. I now weighed 140 pounds. "I haven't been this thin and light since college," I marveled. As a five foot, nine-inch-tall man in his early-thirties, this had been my goal weight for years, and I never would have reached this achievement without the help of my girlfriend, Lisa.

I smile as I stepped off the device, and towel myself completely dry. Then, I sat down on the edge of the tub and started to rub moisturizing cream into my skin, just as Lisa had taught me. That's when Lisa walked into the room and smiled at me. "Someone's being a good girl, today," she said as she reached down and cupped my limp cock and tight balls gently. "Maybe my dirty slut deserves a reward," she whispered into my ear. My big clit jumps in her hand when I hear the words. I know exactly what she means. In fact, indulging in my fantasies is how this petite, blonde-haired vixen has gotten me to lose more than 100 pounds in six months.

Looking back, all of this started unexpectedly, but has roots to my early teens. You see, when I hit puberty, I started cross-dressing with whatever clothes I could find. The laundry hamper was my playground. Then, in college, I would wear the clothes of my live-in girlfriend when she was out of our apartment. I would dress in short skirts, tight shirts, and stockings while wearing a bit of lipstick. Then, I would masturbate and put everything back the way I had found it. No one ever knew of my predilection for female clothing. However, years later, I met Lisa and the urge to explore my feminine side seemed to vanish, that is, until about five years into our relationship, one afternoon.

I work from home (hence the source of my tremendous weight gain over the past few years), and was in my office writing when I grew tired. I emerged to find Lisa sitting on the couch in the living room, working on her computer happily. I told her I was going to take a bath and then go to bed. "How about I give you a nice massage to fall asleep by?" she offered.

For some reason, when she said this on that day about a year ago, I felt this tingling sensation in my chest and knew it would be the day that I let Lisa into my secret, sexual fantasy world. So, I hopped in the tub and shaved my private areas smooth. I scrubbed really hard all over—especially around my hole. Lisa had never before touched me there. But, I just had a feeling that this would finally be the day. I wanted to be super clean for what I hoped were her wandering fingers.

When I got out of the tub, I combed my short hair and put on a tight, pink t-shirt (one of Lisa's), but nothing else and climbed into bed—lying on my stomach. Moments later, Lisa arrived in the bedroom and started massaging me. If she noticed I was wearing her shirt, or how tight it was around my torso, I don't know. She didn't say a word. As her hands worked my body, I started to moan and arch my back. My goal was to slowly stick my ass a little higher in the air with every touch and, soon enough, Lisa got the idea. At first, her fingers delicately caressed my inner thighs of my spread legs. Eventually, she became more daring—allowing her touch to just graze my rosebud. I was in heaven and moaned like a girl with every touch. It was so incredibly enjoyable to be touched so intimately by the woman I loved. Needless to say, it wasn't long before she reached for the bottle of lube and began trying to penetrate me with gentle pokes and prods. "Does my dirty boy like that?" she cooed as she explored my body like never before. "I never would have guessed you could be so dirty, honey. I thought you'd always just be one of those wham-bam-thank-you-mam lovers for the rest of our lives."

I moaned appreciatively and nodded. Then, with a fierce tingling sensation, and a bit of a head rush, I decided to confess who I really was on the inside. "I want to be your girl," I said—correcting her. "I want to be your slut."

"Oh, really," she replied—surprise raising the pitch of her voice. "Is that who you are? I think we can make that happen."

The rest of that session went how you probably imagine, dear reader: Me on all fours and Lisa gently fingering me as she stroked my cock to one of the strongest orgasms I've ever had. After cumming hard, Lisa and I cuddled. We talked about what had happened and I confessed my secret desire to be her lesbian girlfriend in every way imaginable. Amazingly, she accepted me and told me that we could make it happen, if that's what I really wanted.

And, so began our sex games involving dirty talk. I felt like I was in a constant state of arousal. But, I knew first that I would have to lose the weight to truly enjoy this fantasy. I so wanted to look like I did back in college. When I was that thin, I looked so fucking hot dressed in my girlfriend's clothes.

Anyway, as time went on, Lisa and I talked about things more. I told her that after I came, I was no longer interested in dressing. But, I still loved the dirty talk and embracing the fantasy in the bedroom. To her, this was a turn on too. I also told her that I was perfectly happy living as a man. So, we ultimately decided that it would be too difficult and unrealistic for me to live, day-to-day, as a woman. "However, what we could do is slim you down and continue to indulge our fantasies in the bedroom. Would you like that, my little girl?" Lisa asked as she stroked me once to an orgasm that sprayed across us both as we lie on our bed.

"That would be lovely," I said in a whimper of ecstasy.

So, how did I lose all of this weight? Well, I basically became Lisa's Pavlovian dog. She cooked all of my meals. Every day, she would kiss my neck, and whisper into my ear, "If you only eat what I give you today, I'll reward you at bedtime, my slut." And, that's exactly what she did. When I obeyed her, and ate only what she gave me, she would finger me, stroke me, ride me, suck on my tits, eat me out with her tongue, suck on my toes, tongue my ears, and swallow my cum while deep-throating my cock—all of the things I loved—while saying the most delightfully dirty things to make the experience immeasurably pleasurable for me.

"I bet my little girl would like to be fucked by a real cock, wouldn't she?" Lisa would whisper into my ear as she prodded my little hole with her finger. "I think we should both get dressed-up as sluts, find a hot guy, and bring him home so that I can watch him fuck you. Would my slut like that? Or, how about you give me your load in my mouth and then I give it back to you in yours. After all, my little bitch loves to eat cum, doesn't she? Do you want to be my little cumslut?"

Anyway, back to the present. As Lisa kneads my balls in her hand she eyes the scale. "What did it say today?" she said while licking her lips, and then using them to softly kiss one of my exposed nipples.

"One forty on the nose," I said.

"Amazing," Lisa responded. "And, I see you've shaved your legs, arms, and chest like a good girl too."

I nodded silently and continued rubbing the lotion all over my body. From her crouching position, Lisa stood and rummaged in the bathroom closet—taking out a mess of white garments. "When you're done, put these on." Then, she walked out of the room.

Shaking with excitement, I strap the white, lace bra over my chest backward, clasp the ends together and then rotate it around my body—putting my arms through the straps. I don't have any breasts to fill the cups. But, that doesn't matter. I don't mind being a flat-chested lesbian. Then, I spritz on some of Lisa's perfume before putting on a short-sleeved white turtleneck. The fabric is so silky and soft and stretches tightly around my body. The sheer white stockings are next. They slide up my freshly-shaven legs. I attach them to the straps of a garter belt. But, Lisa hasn't given me panties. She knows how sexy I think just wearing a skimpy shirt alone is without a bottom of any kind. I look down at my semi-erect penis and give it a little caress. It feels so smooth. I shudder, knowing how much pleasure I'm about to get from the little, fleshy appendage. I love Lisa so much. She has bought me these things and embraced this side of me. There's nothing I wouldn't do for her.

Finally, I put on some pink lip gloss and look in the bathroom mirror. I look hot. I was never one to want to wear make-up. I have always preferred a much more natural look and a bit of lipstick rounds-out the illusion nicely. Just as I strike a seductive pose in the mirror, Lisa calls out from the bedroom.

"Jessica, my girly girl? I have something you need." When I'm dressed, I'm no longer Josh. I'm Jessica.

As I walk into the bedroom, I see Lisa has put on her corset and a large strap-on. Her longish, blonde hair is tied in pigtails. My mouth waters with anticipation.

"Are you more excited about the corset or my cock?" Lisa asked while stroking the rubber penis as if it were a real dick.

I swallowed with difficulty and shrugged.

"It's okay to like both," Lisa said. "We'll be starting you on corset training soon enough to give you a better shape, my dear. But, for now, let's see if you can take every inch of this."

I lie down on the bed and wrap my arms around my legs—pulling my knees to my chest as the cap from the bottle of lube snaps open in Lisa's hands. She douses my cock, and my pussy hole, with copious amounts of the sticky fluid and then climbs between my legs. "To the outside world, you will be my man," said Lisa. "But, here in the bedroom, you will be my bitch. We will spend hours every day playing dress-up. We'll do everything that girlfriends do, and then some, my dirty girl. I am going to make you into the hottest slut imaginable. Time for your fucking."

I nod and close my eyes. As the head of the strap-on pushes at my hole, I have never felt so girlie and alive. I can't wait to see where our play takes us next.