This journal has been very difficult to keep over the last several months. I can't even begin to write extensively about this without getting so caught up in the fantasy that I end up not writing anything. Here's another futile attempt to tell the same old story.
My girlfriend caught me looking at pictures of Imogen Bailey. She was devastated. Imogen Bailey is probably the most incredibly gorgeous woman on the planet. Jenny, whose self-confidence was low to begin with, in spite of her own considerable beauty, took this as a betrayal.
"I try so hard to be beautiful for you, and yet you still look at other girls!"
"You are beautiful!"
"So why are you looking at her?"
"She's beautiful too."
"Is she more beautiful than me?"
Great. A dangerously loaded question. My hesitation alone gives Jenny's argument momentum.
"See? You think she's more beautiful than me!"
"That's not true," I lie.
"So, I ask you again, why are you looking at still pictures of her when you can look at me, a real, living, breathing woman, standing right here?"
"You're being irrational."
"Answer my question!"
"I'm sorry, but she's a beautiful woman. You can't expect me to stop looking at other women just because we're living together."
Big mistake.
"Then maybe we shouldn't be living together."
I have dug myself even deeper into the hole. This will not be easy.
"Jenny, you know that I love you, and that I wouldn't ever dream of being with another girl. You know that you don't need to compete with other women."
"So are you attracted to Imogen Bailey?"
"I'd be lying if I said otherwise. But that doesn't mean I don't find you outrageously beautiful too."
"I sure hope so. I've been trying so hard to look like her, just to please you."
"Honey, I love you exactly as you are. You don't need to try to look like anyone else."
"Well, if you look at Imogen Bailey so much, then I need to draw your attention away from her and back to me."
"You don't need to. I am all yours."
"So why do you need to look at her?"
Again, my hesitation kills me. I just don't know how to answer this diplomatically and truthfully at the same time.
"Tell me!"
"I look at her because she looks like you, not the other way around." Another lie.
"I'm sick of this. Obviously, I've got it all wrong."
"What do you mean?"
"You're so evasive about this. I've tried so hard to be Imogen Bailey for you, and it hasn't mattered. Maybe you look at her for other reasons."
"Like what?"
"Oh, let me guess: you're interested in her political views."
"What?"
"No? Of course not, she has none. You are after all just looking at her pictures."
"Yes, we've established that."
"Fine then. So you look at her because she's pretty and sexy. Nothing else."
"What else do you want me to say? If you know so well what she looks like, and if you're trying to look at her, then maybe I should be jealous, too."
"I don't look at her because she gets me off."
"Neither do I." Oops. Barefaced lie.
"Really?" she asks, skeptically.
"Really," I assure her.
"Then maybe you look at her for the same reasons I look at her."
"What's that?"
"You want to be just like her too."
"What?"
"Yes! That's it! You want to be blonde and curvaceous and have big tits and look dynamite in a bikini!"
"Now you're being silly."
"All right. If that's not the reason, then you're looking at her because she gets you off, and if that's the truth, then I'm leaving you."
"You're serious!"
"Yes, I'm serious."
She is serious. Clearly, I must do her bidding or lose her.
"Please don't!"
"Why not? Does she get you off?"
"Well..."
"Fine! I'm out of here!" She turns to go. I can tell that she means it too. I grab her arm and pull her back.
"Please, don't go!"
"OK. Here are your options: if you look at pictures of Imogen Bailey to get yourself off, then I'm not your girlfriend anymore. If you do it for the same reasons I do - because you want to look just like her, then I'll stay."
The trouble is that Jenny really does look like Imogen Bailey. And she's a very smart, kind, and generous woman who shares my taste in music, movies, food, and books. We are a wonderful match. I love her deeply, with all my heart, and I can't allow her to leave me. Curse that Imogen Bailey! I cave.
"Jenny, don't go. She doesn't get me off. I swear it."
"Oh yeah?"
"Yes."
"So you want to be just like her, as much as I do?"
"Yes." I'll say anything to keep Jenny.
"Really?"
"Yes."
"Say it!"
"I want to be just like Imogen Bailey, and that's why I look at pictures of her."
"How do I know you're not just telling me what I want to hear?"
Good ol' Jenny, always as sharp as a tack.
"You'll have to take my word for it."
"Well I don't believe you."
"What do you want from me?"
"Prove it!"
"How?"
"Prove to me that you want to be just like Imogen Bailey!"
"How can I do that? I can't be like her."
"Don't you want to?"
"Yes. I told you."
"Then you'll have to make an effort to look like her if you want me to believe you."
"What do you mean?" I'm on my knees, begging her. She's beaming down at me devilishly.
"Do you really mean it when you say that I look like her?"
"Yes, you really do look like her."
"So my efforts to look like her have worked?"
"I would say so, yes."
"So just follow my advice, and you'll do just fine."
With that, she brought me back to the computer, and quickly found my stash of Imogen Bailey photos. She skipped past a few nude shots, and settled on one of her in a bikini.
"You want to look like that?" she asks.
"Yes," I reply, still playing the game.
"You know that I have a bikini just like that, because of this very photo?"
"You know, I did notice that."
"Good. There's how you start."
"What do you mean?"
"Get yourself a bikini."
"What, like that one?"
"Sure. If you like another one better, go for that one."
"This one is fine."
"I thought so too. You can borrow mine if you like." She disappears into the bedroom. I can hear her rummaging around a bit.
"Wait a minute. Why am I doing this?" She asks. "You're supposed to prove to me that you want to look like her. Why don't you come here and pick it out yourself!"
Before I know it, I'm picking through her panty drawer for Imogen Bailey's bikini. I feel awkward looking through her intimates, as if I'm doing something dirty. I feel as though I'm discovering things in her dresser that no man should know about.
Having found the bikini, I take it out of Jenny's panty drawer, and present it to her, bra in one hand, panty in the other.
"What are you giving it to me for? You're the one who wants to look like Imogen Bailey."
"What do you want me to do with it? Wear it?"
"Of course. How else are you going to look like her? I doubt she'd ever wear your kind of briefs.
Reluctantly, I disrobe, under her triumphant gaze. I tremble as I pull on the panties. The soft spandex caresses my member so gently that it instantly and involuntarily becomes erect. Jenny giggles at me. "The bra, too," she says.
I struggle to clasp it behind my back. After a few minutes of struggle, through which Jenny giggled incessantly, I finally got it on properly. There I stood, in front of my beautiful girlfriend, wearing her bikini, my hard cock straining against the tight panty.
"There!" she says. "You don't look anything like Imogen Bailey, but you look at lot more like her than you did an hour ago. How does it feel?"
I could feel the blood rushing to my cheeks. The panty is high-cut, and exposes the side of my thigh all the way up to my hip. The material is very soft to the touch. I love the way it looks on Imogen and on Jenny. I can't stop thinking of how sexy both of them look in it. The sensation of a tight band around my chest reminds me constantly that I'm wearing a bra. The bra straps feel dainty against my broad shoulders.
"I kinda like it," I reply, shyly, blushing, and trying very hard to convince myself that I am lying.
"Wow! It shows, too. Why don't you prance around a bit, like Imogen would."
I can't help but get into the act. I'm swinging my hips, sashaying around the bedroom and running my hands against my breasts, my butt, my hips, my thighs, as femininely as I can. It's getting me incredibly hot. Jenny drops her jaw in amazement. She's looking randy, too, and she starts to prance around with me, feeling me up now and again. I am lost to the moment. I am Imogen Bailey, I am Jenny. And I feel sexy in a way that I never have before. A little voice in my head warns me that I am not a woman, and that I'm jeopardizing my manhood by doing this. The overwhelming sensations in my body scream in assent YES, I'M TURNING INTO A GIRL AND I LOVE IT! I imagine the panty re-shaping my crotch into that of a woman. I imagine my waist sucking in. I imagine the bra filling with my own full breasts. I welcome my imaginary metamorphosis not with open arms, but with greedy, grasping arms.
I have ejaculated all over myself, and all over the bed sheets. I have come crashing back to earth. Jenny has stripped to her underwear, and lies beside me in bed, flushed. She has her hand in her panties. I am flushed with shame, aghast at my actions. She says nothing until she finishes coming.
"Geez, Rob. You must really love me. You're still wearing my bikini," she breathes.
Disgusted, I clean up and get myself out of her bikini.
"You know," she says, "I think you'll make a great Imogen."
"Are you happy now?"
"Yes!"
"Good."
"I hope you don't think this is over."
"Why not?"
"I still don't believe you really want to be Imogen."
I say nothing, stewing in my shame.
"I'm satisfied for now," she says, "but you've still got a lot of work to do."
Thankfully, my plentiful stock of Imogen Bailey photos remained on my hard drive, forgotten in the frenzy described above. Jenny would normally have had me delete them all, but this time, she forgot. Or perhaps she felt she humiliated me enough, and didn't need to punish me further. Better still, I had no shortage of other gorgeous women on my hard drive. I went back to them the very next day, just to spite Jenny.
I am furious. How dare she mock my masculinity? She showed no respect to my manhood. She turned me - ever so briefly - into a prancing faggot. It was bad enough that she made me wear items of her clothing; even worse that it was one of her sexiest, skimpiest outfits; worst of all, and I shudder to think of it, she made me enjoy it. I nearly faint with shame when I face the intolerable truth of it. How can she ever take my manhood seriously again? Hell, how can I?
These photos take on an entirely new meaning for me. I cannot allow her to ruin this for me. I linger on the picture that triggered all this madness. I wore that same bikini! I still have trouble believing it, let alone comprehending the consequences. I used to jerk off to this photo. Now it reminds me of my humiliation. Maybe that's why Jenny didn't remember to delete it. My heart sinks with humiliation.
I need to relieve some tension. I need vengeance. I am stroking my cock, admiring Imogen's firm, round breasts, her glorious waves of golden hair, her sleek, slender thighs, and the way they converge in that soft, delicate pocket of thin, scanty spandex such as I wore only last night. Oh how I love the way she poses, so sensuous, so eager! How her tight little bikini focuses her femininity (I know how that feels). I can just imagine sliding my hand along her round little ass, snapping her panty waist (as Jenny did mine).
You enjoyed it, didn't you! You loved every second of it! You dressed up like a girl, and you liked it!
My conscience's accusations, as much as I attempt to deny them, drive the intense pleasure in my massively erect dick. I know that I can't continue to stroke, because I am still, paradoxically, undermining my manhood. I want to be just like Imogen Bailey! I want to be soft and curvaceous and blonde and slinky and scantily clad gorgeously femi-
No! I must control myself. This is absurd. I want to fuck her. I want to throw her roughly onto my bed, hold down her arms, and force myself into her, as she gasps for breath. I want to grab hold of her ass as I pump my love juice into her.
Amazingly, I lose my groove. I am no longer pumping. I am failing.
Unacceptable! I cannot allow Jenny's mind games to prevent me from masturbating with sexy pictures of other women. I must come, if only to establish control again. I know just the thing to turn myself on again, I think slyly to myself. I can imagine myself as Imogen Bailey, wearing that sexy lit-
I am losing control again! But I'm also going to come! If I come, I win because I defy Jenny; but I also lose because I surrender my manhood . . . and what could be better? I think to myself lasciviously, Doesn't it feel wonderful being feminine? Oh God! Does it ever! Wouldn't it be wonderful if Jenny caught me right now and made me wear her bikini again! Or maybe her lingerie!
As I clean up, I rationalize my capitulation by convincing myself that this was an act of defiance. I am ashamed, but I won't admit it. I know that last night's incident has indeed adversely affected my masculinity. But this won't happen again. Ever.
"So, Imogen, are you ready for another show?"
I can feel the blood rush to my face. My legs are weak. My hands tremble. "That's not funny, Jen."
"It's not meant to be, Imogen." She spits the name, like venom. "Put it on."
I reach into Jenny's panty drawer. I know exactly where to find it now. Oh God! Look at all that pretty underwear! Wouldn't that be- I must concentrate on controlling myself. I cannot show pleasure again. Oooh! Silk! I have the bra in one hand, the panty in the other. Again. "I don't understand why you insist -"
"You're the one who wants to be Imogen Bailey, aren't you? Or did you lie to me?"
I've lain the bikini out on the bed. I don't want to wear it. I can't wait to put it on! I'm hoping that if I concentrate enough, I can avoid succumbing to my overwhelming urge to feel feminine! My delaying tactic is only making things worse: my erection grows ever larger as I anticipate the horror ecstasy to come. I have to admit, it is an incredibly sexy bikini. I have to put it on now - just to hide my boner, of course. Of course.
I am trying incredibly hard to pretend that this annoys me. Yet I caress my bikini-clad hips. I want to show Jenny that this has gone far enough as I hook on my bra like an expert. I want her to know that I don't really want to be Imogen Bailey, that I'm just doing this to please her and to keep her. I'm playing coy just like a shy girl. I pout to show my displeasure.
"Oh, don't be sad, Imogen," she says, standing up now to caress my effeminated body. "You look very pretty in your bikini." She rubs my pulsating member through the spandex as she says this, and I practically collapse at her feet in a heap of sensuous femininity. I'm a girl! I'm a girl! I'm wearing a bikini! I'm a girl!
Like the first time, I prance and preen like a supermodel for my lovely Jenny. Only this time, I'm consciously loving it. What better way to convince her that I'm sincere? She'll surely believe this act. If only it were an act!
When it's all over, and I've cleaned up my mess, I know that I have lost again. Jenny smiles smugly beside me in bed, having masturbated herself to orgasm with me. Even as I strip off my bikini in disgust. As I toss it across the room, I realize that I have seen Jenny do the same thing herself. Even in my belated denial of femininity, I am flushed with girlishness.
In our time together, I have handled some of Jenny's laundry. I have separated out her underwear from mine. I have handled her silks. I have bought her lingerie for special occasions. I have seen her in her most intimate undergarments. I always found her clothes to be inherently sexy. I always felt a surge of intimacy at the realization that I have been allowed to see and touch her almost sacred underthings. Now I find myself yearning to explore that intimacy in far more detail than ever before.
I am pawing through Jenny's underwear drawer. Piled in with her bikini are myriads of matching and unmatched panties and brassieres, two garter belts, a one-piece swimsuit, sexy nightgowns and satin teddies. Silk panties melt out of my hands like water. I hold them up, one at a time, and admire the flowery lace patterns, and the beautiful trims. All of these things are so ridiculously feminine. Many of them even outshine the bikini I've actually worn.
Jenny has not insisted for almost a week now. I have had time to think about my actions. All sorts of insignificant things trigger memories of my two incidents with this bikini. Embarrassingly, these memories arouse me. Clearly, my wearing it has tainted my manhood. I find myself longing to wear it again. Worse, I find myself fantasizing about even sexier garments. Imagine how much more corrupted I would be if Jenny had forced me to wear her lingerie instead. I shudder with anticipation.
I figure that I might as well prepare myself for the possibility by examining all the options. Perhaps if I know beforehand what I might have to wear, I can lessen its impact. Perhaps if I know beforehand what's available, I can pick something really sexy, like a garter belt and stockings, or a ni-
Curse her!
I place everything gingerly back in its place, livid with shame, and go masturbate.
Tonight Jenny comes home with a present for me. There is no special occasion. She beams with a sinister joy.
"I bought you something at the mall!"
"What is it?"
"Open the bag and see!" She practically bounces off the walls with excitement. I open the bag.
All I see inside is what appears to be a bikini.
"I thought that since you want to be like Imogen Bailey, there's no sense in you borrowing my bikini all the time, so you might as well have your own!"
It's another bikini, all right. It's a similar one from another of my pictures. A floral pink. Just my size, too, maybe a little smaller.
"I'm so glad you like it!" she gushes.
I am, of course, ashen and trembling; I can hardly see anything except the sexy, skimpy, ultra-feminine bikini in my hands. Oh my God! I never imagined I'd get to wear this!
"We're gonna have so much fun tonight!" she says, rushing upstairs to get changed. I follow her zombie-like, and tuck my new bikini into a corner of my own underwear drawer.
Dinner is interminable. I can hardly eat a bite. Jenny babbles on as if everything is normal. We wash the dishes. We put away the dishes. We watch a bit of television. I have my very own bikini waiting for me in my underwear drawer. How am I supposed to react? I realize that I haven't spoken a word since I opened the shopping bag.
At length, she cuddles up to me lasciviously and whispers into my ear, "Let's try on your new bikini."
"Okay," I answer, automatically. She leads me up to the bedroom.
She sits on the bed, waiting. I lose no time in stripping down, and reaching into my drawer for my new bikini. I don't think I should be doing this. It truly is a gorgeous piece of work. I can just imagine how erotically it will hug my hips. I can't let her see me enjoying this! It's not right! I'm losing my manhood!
I step into the panties and slide them up to my crotch, savouring the touch of spandex against my cock. I slowly strap on the bra, revelling in the realization that I am putting on a woman's bikini that happens to belong solely to me. I have wantonly abandoned any pretense of hesitation or displeasure. I close my eyes and slide my hand across my chest and cock, imagining myself metamorphosed into Imogen Bailey herself. I'm effeminating myself in front of my girlfriend, and I just don't care! Inspired, I sidle up to Jenny, who sits on the bed watching.
"Thank you so much," I whisper in her ear seductively, "I always wanted my own bikini."
My God! I can't believe I just said that!
"You really like it?"
"Yeah," I reply, coyly. "I love it!"
"That's so cool!"
She drags me onto the bed, where I strip her to her underwear, and we make out, comparing bras and panties and body parts. It is the most sensuous lovemaking I have ever experienced, yet neither of us is fully naked.
Even after last night, I suspect that Jenny believes I'm still just playing the role. I only wish I were. When I woke up this morning, still wearing my bikini, it took every every ounce of my willpower to take it off and put it away. I could think of nothing else all day.
It's one thing to wear it to please Jenny. I can always fall back on the excuse that I'm doing it only for her, even though I know that's not true. It's quite another thing to have an overpowering urge to wear it now, alone, to get off. Am I insane?
It's so easy. I have my very own bikini. It amazes me when I look into my underwear drawer, and see this pink floral bra and panty among my butchy boxers and gitch. I want more! I want my underwear drawer to look much more like Jenny's, when I get in this kind of mood. I want to be able to wear a matching black lace panty and bra. I want to have elaborate silk and satin unmentionables.
I just can't help myself. I pick up where I left off this morning, and slip into my very own bikini. By God, look at me! I'm wearing an unmistakably feminine outfit, and it's turning me on! I did it of my own volition! And I'm fantasizing about doing it again and again, with all sorts of women's fashions! I am a complete pantywaist! I know that wearing this - especially unsupervised - is making me even more of a pantywaist! This is turning me into an outright woman! And I love it!
If only Jenny knew how much I really enjoy this. I can't let her find out I'm doing this on my own. I know she's only playing the game. She doesn't really want me to turn myself into Imogen Bailey Oh my God! Even though I'm fantasizing that my bikini is shaping my ass into a round, tight little girlie ass, and smoothing and sculpting my waist, and swelling my chest into a perfect pair of perky, round titties.
She must not know!
This is the third night since Jenny returned from her mother's. We had sex the last two nights. Frankly, it was a bit dull. There was no mention of the new addition to my wardrobe. I am desperate to get into something feminine - and watching Jenny lounge around the bedroom in her frilly little nighty does nothing to assuage my desire.
When she comes to bed, I leave a light on and cuddle up to her, fondling the waist of her panties and the spaghetti straps of her nightie. "You look so incredibly sexy in that nightie," I whisper, imagining it on me instead of her.
"Thanks," she replies coyly.
"I love the way it caresses your tush."
"I kind of figured you'd like it."
"Do I ever!"
The last two nights have not included this kind of sexy pillow talk. We tore our clothes off and fucked our brains out. In fact, I never used to remember to compliment her on her lingerie. I was more interested in what was underneath it. The last time I said things like that, she repeated similar compliments to me.
We are making out. I am not even attempting to remove her nighty. I am imagining wearing it as I rub my naked chest against it. What would it feel like to wear satin?
"Do you mind if I slip into something more comfortable?" I ask.
Jenny grins. "Please do, Imogen." Busted.
I sheepishly get my bikini and put it on for her, in a reverse strip-tease. I am openly staring at her nightie. There's no hiding my desire. I am wearing a bikini in front of my girlfriend, and fantasizing about wearing her sexy nightgown. What is happening to me?
She pulls me into bed, and we fondle each other in sheer bliss for what seems like eternity.
"So, you really like wearing bikinis, do you?"
"Uh-huh."
"Are you doing it just to please me?"
"Uh-unh."
"Why, then?"
"Because," I reply shyly, luxuriating in my femininity, "it makes me feel so sexy."
"Mmmmmm, and you are sexy!"
I can no longer even pretend to deny it to her anymore. I feel somehow relieved. Free at last!
(I dare to throw away the bikini in a moment of shame)
(When the ritual occurs, and the bikini is gone, she is furious. I am eager to please, so I volunteer to wear some of her underwear, and to buy her (me) a replacement)
(I practically lose my mind in a swimwear store)
(I parade an inexact replica for her, without prompting)
(I experiment with all her clothes when she's not there)
(I experiment with all her clothes when she is there)
(I surprise her by wearing her panties all day)
(We shop together for my new under-wardrobe)
(We sleep in matching nightgowns)
(I shave away my body hair)
(I perfect a convincing feminine look with Jenny)
(I begin to take estrogen)
(I suck her new boyfriend's cock)
(I publicly take on a female identity)
(My new boyfriend fucks me)
(I become a real girl)
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