Trading Pics

Entering the bedroom John was on the bed. On the wall facing the bed there was a big TV with porn playing, the sound down low. At first it didn't register but it was twinks in panties kissing and playing with each other's cocks and taking turns sucking on a "Daddy" cock. Must have been what turned John on the most hence his Craigslist ad. He must have been thrilled living out his porno fantasies in the flesh with me. When he saw me, he let out a catcall whistle.

"Wow, Baby," was all he said as he then sat on the edge of the bed.

The look of desire in his eyes made me feel like a million bucks. I stopped, flipped my hair back like 1960's go-go girl actress and put my hands on my hips. By now I had become one with the role I was playing.

"You like?" I asked. Almost sounded like the broken English a cheap foreign whore would use.

"You have no idea sweetheart. Wow!" John gushed in his New York accent.

Wanting to milk it some more I pranced around the room showing off my sexiness. In the high heels I was floating. Had no idea they'd make me feel so good, so feminine. Words can't do justice to what I was feeling. This persona I had morphed into in such a short time was otherworldly. Maybe because I still hadn't cum it was driving the intensity of my theatrics. The window was open a crack. Birds chirped outside. Here I was, a boy, in the bedroom of a stranger, in his wife's high heels and bikini swimsuit about to have sex with him. For the second time.

"Come to Papa, Princess." John could wait no longer for me.

Sauntering over sexily in the fabulous high heels, I stood next to him. Spreading his legs apart I moved between them. Placing his hands around my waist he began admiring and exploring my tender body.

"My wife never looked so good in this," he told me as one hand lightly brushed my ass. That made me proud.

Soon his other hand slid under the bikini top. His index and middle finger toyed with my nipple. Playfully I lifted the top and flashed John my "titties". He shook his head in disbelief. Leaning into him we kissed a soft, slow, light, tender kiss. It was one thing go over to a stranger's house and suck his cock. Those type of anonymous sexual encounters happen all the time. Usually, they end with both parties zipping and splitting as fast as they can. This was something entirely different. One party was fantastically enamored by the enchanting transformation of the other. Both of our cocks were hard as stone. Still, I had yet to cum. I pulled loose the bikini top strings and was soon topless. Being topless made me feel sexy. It made me hornier than hell. John pulled me into him as we melted together on the bed. John's masculinity enveloped me. My hand rubbed on his cock as we kissed, this time like crazed beasts.

Breaking the kiss and looking in amazement into each other's eyes I hesitated not at all getting my mouth back on his cock. Had to taste it again. Fucking tasted so good. Beautiful helmet head on his engorged penis filling my mouth with cock. Think I could've spent all day with it in my mouth. For so long I had teased men online trading pics of me in panties for pics of their cocks. It excited me but I had no intention of ever sucking one. I wasn't gay. It was just my pantie fetish. A fetish that made masturbation fun. And just like that for no apparent reason I went ahead and succumbed to one of the many men who desired me. I wasn't gay. Silly me. Sucking cock in high heels and women's clothing sure beats jacking off in panties to pics and porn.

John pulled me up. Think he wanted to play some more with his bikini babe. His big paws were all over me. Reaching into the bikini bottoms he played with my cock. I didn't mind. Pulling on the strings soon his bikini babe was now bottomless too. Groping my ass cheeks in each hand I fell into him as we made out again. Before I knew it, our cocks were rubbing together as we kissed and my ass was being groped. One of his fingers found its way to my tight bung hole. It felt good to be fingered but a shiver of fear told me I was not ready to get fucked on a first date. Still, fingering, frotting and kissing was OK by me. John lay me back down with my high heels towards the pillows as he lay opposite as we turned into a 69. Yum. Double dipping. His cock found my mouth as he began to lick at my hard little peeny. After this a short time of being a cocksucker I knew I could suckle on his penis all day.

Surprisingly the 69 did not last very long. He flipped me over on my stomach, spread my legs and dove his face between my ass cheeks. Now I had heard of them but(t) had no basis of knowledge in regards to a rim job. Now first-hand I knew. OMG would never imagine that someone would lick my tight little puckered hole, or what kind of impact it would have on your privates. My girlfriend certainly would never have done this. I did know that part of the anatomy of fem bois and twinks was often referred to as 'pussy' by alpha males. So, with John licking my pussy, and boy did that feel as good as anything has ever felt, I sincerely was not ready for him to stick something else in my "pussy", specifically his cock.

"Papa wants to fuck your sweet little ass," John said as he came up for air and dread creeped into my life. "But I don't want to hurt my little princess so I'll just play with it a while and then we can both cum."

Phew! A minor relief for me but now it was time for major relief for my penis. John humped his cock between my ass cheeks, even pressed it against my tight bung hole a few times, sizing it up, I guess. Tip of his penis smeared pre cum over my tight hole. It did feel good but I was not ready to get fucked. He rolled me over and we kissed and frotted a bit more. I still had the high heels on and felt oh so slutty. I still had not cum. Was hoping to change that soon. John reached into the drawer of the nightstand and pulled out one of Kathy's vibrators and some lube. It was a pretty pink cylinder not nearly as big as John's cock.

"Papa won't fuck you today but let's give this a test drive," he smiled as he lubed up his middle finger and inserted it into my anus.

Felt good so far, had to admit. Lubing up the vibrator he slowly worked it up my butt. Ouch very little and "schwing" in my penis as he turned the phallic device on. John pulled me up into his arms, his warm breath in my face, then he put his mouth over mine for a loving, consuming kiss. It made me tingle. For never really having thought about or desiring to kiss a man before today, I had to admit kissing the uber masculine John heightened my sense of femininity. It made my penis hard. So did the humming pink love stick he was poking in my hole. Writhing in pleasure I jacked on my cock as I lay my head on his shoulder in one of John's big arms while he held the vibrator in his other hand. I might finally get to cum. After all my girlishness and dressing up and being lovey dovey with John's penis I was close. Actually, I was there. With my hand moving like a piston coaxing my penis, sperm cummies squirted out all over me as I gasped in exasperated relief.

"You're a doll, Sweetheart," John told me as he kissed me lovingly over and over again as I continued squeezing pleasure out of my rigid little peeny.

I was drenched in cum, naked save for his wife's high heels, in this big man's arms. It felt funny as he pulled the vibrator out of my "pussy". Dreamily I lay my head on his chest slowly coming down from this sex induced high. His big hard cock was right there. Playfully I traced my fingers over it. John "hmmmed" softly. The thing was massive, standing tall in a forest of dark pubic hairs. Hard as stone yet tacky to my touch on its velvety sheath I began jacking on it. We kissed again. Not sure exactly if what I was feeling was romance but it was intimate, tender and loving, certainly not a "wham, bam, thank you man" gay experience.

It was thrilling to pleasure John in this manner after I had just done the same to myself. After many minutes of playing with cock his breathing got heavy and he placed one of his big paws over my hand pressing it into his penis. He let out a low moan as a flood of cum splattered out of his cock over our hands and bodies. When his orgasm subsided, we kissed again. Instinctively I reached my face down to his still large cock. I had to taste it once more as I lapped up a few gobs of cum and put his cock back in my mouth. Hard to really put into words the wonderfully nastiness of the tangy, bitter taste of his cum and cock, especially now after I had already cum, so my heightened libido had dissipated and was not edging me on.

We lay in each other's arms for a bit as the after-sex realization of what I had just done set in. I had dressed in the clothing of a strange man's wife and engaged in sexual acts with him. I had always thought I was straight, even when masturbating in women's panties and soliciting images of cock from men on the internet. Now I was not so sure. Was not even sure I had done the right thing as I took a washcloth in the bathroom and cleaned the makeup off my face and the blotches of dry and still wet cum off my body and penis. A sense of weirdness hung over me. Before I had finally cum a few minutes ago, being a faggy fem boy in women's clothing and fawning over John's large penis, acting like a girl and kissing another man it was the most exciting thing I had ever experienced in my life. Now a fog of doubt rolled in. I had called in sick at work to have sex with a man, dressed in his wife's panties, dress and clothing. Not even wanting to go there but what would my girlfriend and co-workers think if they knew?

Dressed my boy clothes and ready to go John was very kind and not weird. He was affectionate, loving, he hugged me, held me, told me I was a "keeper" and "not to worry, it was a good thing today, wonderful in fact," and "don't feel bad, you were amazing" in his east coast accent. All of which made me feel worse, more guilty and I could not tell if he knew I was freaking out inside. John told me to call or email any time.

Driving off in my car from John's house a deep sense of shame washed over me. I had deceived my girlfriend and called in sick at work to have sex with a strange man, dressed in his wife's panties and clothing no less! Feeling very guilty, utterly ashamed with myself, I vowed I would never do it again. Tears welled up in my eyes, I still had a faint taste of lipstick on my lips. I tried to rationalize that everything was OK, that I needed to try it once to get it out of my system. There, it was done. I could go on with my life as a straight guy and be a good boyfriend to my girl. We might even get married.

When I got home it was still many hours till my girlfriend got home. I was hungry, famished, and fixed a sandwich and sat on the couch. Turning on the television I tried to get my mind off what I had done. Still, a sense of shame hung over me like a cloud, like I had committed a horrible crime. Zoning out on some mindless TV I slowly started to feel a little better. After quite some time I turned it off and tried to take a nap on the couch. My girlfriend would not be home for another hour and a half. My legs, pubes and underarms felt strange being shaved and that feeling was a constant reminder of my shame of the egregious deed I had done. Just as a passing thought of what had happened, what I had done with John, the unthinkable happened. I was getting hard again! No, no, no! Don't! Can't be happening, what I did was over, will never do it again. Yet here I was with a raging hard on and the thought of putting on some panties right now snuffed out any sense of shame I had felt, no matter how immense the shame I had lived in the past few hours.

Like a zombie I headed to my secret stash of panties and pulled out one of my favorite pairs, a silky side tie bright pink string bikini panties. They always felt good on but now they felt amazing on my shaved legs and balls. I was every bit as hard now as I was with John, maybe even more so. In the bathroom I admired myself and my sexy girlish figure, now nearly completely shaved. I had trimmed my pubes short, shaved all but a tiny 'landing strip' and shaved my balls in the shower this morning. The silky panties felt heavenly on my shaved privates.

In the vanity was my girlfriend's makeup and lipstick in the drawer. In a daze I knew I had to put some on. Toying with blush, eyeshadow, mascara and eyeliner I became a girl again. My hands fairly trembled as I put on some soft pink lipstick, John would have loved seeing me like this. The thought of calling John for phone sex crossed my mind, I was so hard. After John had played with my ass with his wife's dildo, I felt like playing with it too as I stroked my cock. My girlfriend had no such devices and really with her sex was about as vanilla as it gets. I doubt if she had even masturbated. In fact, I knew she didn't when I tried to get her to do it one time and she poo pawed me saying she's not that kind of girl. While she did not have a very religious upbringing her very conservative family life did nothing for her libido.

I rummaged around under the sink found a small jar of Vaseline and took a towel from the closet. I headed to the bed with an old hair brush of hers that had a long round plastic handle. Looking at the clock it was about the time I was usually home and she would be home in an hour or so. With some tranny porn on the laptop I stroked my aching pantie clad cock and prepared to insert the makeshift phallic device up my ass. The phone rang. Oh shit! Scrambling off the bed I answered. It was my girlfriend. She was being sweet and asked me what I would like her to pick me up for dinner. My mind was scattered. I muttered something like "pick up whatever you like."

"Are you OK?" she asked. "You sound different."

"No. I'm OK. I just don't feel well," I lied. "Pizza sounds good."

"Alright, I'll see you about 6:30," as she hung up.

She can tell something is up. I'm screwed. You idiot. What are you doing? Dumb fuck. It was a quarter past 5 so I had a little over an hour before she got home. I had lost my erection on the phone call and went and peed, sitting down like a girl. Maybe I should just take a shower and wash off the makeup and wait for her to get home. But seeing how sexy I looked in the mirror as I wiped my pee pee with some tissue the erection soon began to grow as I pulled up the sexy pink panties and admired my hottie little ass in them. On the bed with the porn on the laptop my cock felt wonderful. I slipped a finger inside the panties and fingered my little hole. That felt wonderful too. I pulled the panties down to my ankles and lubed up the brush handle. Laying on the towel I poked around trying to insert it as the sexy sensation of putting something up your ass drove me on. John wanted to fuck me; would I like it? If how the handle to the brush wiggling up my ass felt, the answered would be a resounding yes.

Poking the lubed handle up my hole it was both unnatural and wonderful at the same time, just like when John poked his wife's vibrator up my ass when I was in bed with him. The sensation was driving me wild as I pulled on my cock. I did not know really what it meant to feel like I did, but I felt so gay. Just knowing that putting on panties and sucking a man's cock made me feel like I had never felt. It was exciting. It was an obsession. I did not understand. What was happening to me? Why, why? Why was I like this? Normal guys don't wear panties (and suck cock).

This was a delicious, naughty jack off session. I knew it had a time frame to meet. My girl would be home in an hour or so. I still had her makeup on. Working the handle up my butt, it started feeling good. The porn on the laptop on the bed was exciting, Emo twinks in colored boys' underwear or stockings kissing each other, feeling each other's cocks, sucking off each other, one of them fucking the other. In other videos there were twinks sucking cocks and getting fucked by Daddy types. I was fascinated. It was exactly what I had just done with John. Must have had more than a dozen tabs open with different porn videos playing. My cock was tacky, sticky in my hand as I jacked it off with my hand as I fucked myself with the brush handle with the other hand. I was gulping in air and writhing around possessed with this offbeat sexual obsession. Not really grasping why but with the handle far up my butt my cock was hard but it felt different, a different type of sensitivity than a normal jack off. Then I started to cum. It too felt a little different. But it felt good. As the cum dribbled and spurted out it was different as well but the sensation in my butt consumed me. When it was over, I just lay there. Everything I had done today registered with a strange realization. My life might never be the same. Cum was all over my belly. I pulled the brush handle out of my ass.

Fuck! What was that? I thought I heard a noise. Was she home already? Jumping up, I ran to the bathroom. Oh fuck! The gay porn is still on. Running back, I closed the laptop and ran back in the bathroom. I was a mess. Cum was all over my tummy. I listened. No, she was not home. Great. OK let's take a shower. Wait, if I shower now, she'll know something is up I showered this morning. But I don't "feel well," right? Nah, won't take a shower, will just use a washcloth. So, I took all the makeup off with soap and the washcloth. Then there was makeup, mascara and lipstick on the washcloth. Fuck! Will have to wash it tomorrow or throw it away. I'll just hide it under the sink for now. Had my cummies on it too. I was a mess.

When she came home, I could barely look her in the eyes, she was so sweet to me. She had brought me a flower. I had cheated on her, with a man! And she was loving and sweet and kind to me, having no idea what a piece of crap I was for doing what I did today with John. And fucking myself with her brush handle wearing her makeup in a pair of pink panties. Good boyfriends don't suck cock in panties behind their girlfriend's back. She babied me a little because "I did not feel well." We ate pizza on the couch. I was zoned, a zombie. I did not feel well. It was not because I was ill, it was because I was such a low life closet fag cheating on my wonderful girl with a man. I was having a bad case of the "heebie jeebies". I felt so weird.

Then after watching TV for most of the evening, she was in the bathroom for the longest time. An ungodly long time. Did I leave her lipstick on counter? Fuck, it was in drawer before I used it. Did I put it back? You dumb fuck. She had been in the bathroom a couple of times since she got home, girls notice these things. When she got out, I went in the bathroom to check it out, no, it looked like I put everything back in order. Unless I left it out and she had put it away. Looking in the mirror, OMG, no! I still had makeup on, a touch of lipstick at the corner of my mouth and blotch of blue on the eyelid, that must have been from John's house. She didn't notice, did she? If she did, she didn't say anything, not that she would, she was timid and hated any type of conflict or scene. I was a mess. After a day of such a roller coaster of emotions and intensity of sexual activity, I was beat. Finally getting to sleep to end it for the day was what I needed.

Next day was Thursday, was so glad to go back to work and get back to the routine. Was a model citizen in the afternoon after work at home waiting for my girl; no porn, no panties, no masturbating. Ditto Friday. Saturday, I slept in with my girlfriend. Something seemed different since that day with John. Did not try to initiate sex with my girlfriend, actually was still feeling guilty about the sex I had with John. In some ways I was going crazy, I had not cum since the day with John. That was unheard of going this many days without cumming. But with the 'manscaping' I had done on my pubes and shaving my legs and underarms I was afraid what she might think or say. That night in bed I started feeling her up, it was dark she wouldn't see the shaved parts. She felt good, I was so horny. I loved her little titties, so fine to touch and kiss. Her pussy tasted good; I loved her pussy. It was so good having sex again, see I wasn't gay. Fucking her felt so good. Then something happened. Never happened before. I was losing my erection! Going soft!