I met Mark online.
I’d joined a gay chat room. I had been fantasizing about being with a man for a while and this was a harmless, anonymous way to explore my interest.
To begin with, I was very shy and didn’t know how to respond to the occasional message that came my way. Then I got into a conversation with a guy who made all the running. I only had to go along with his messages.
I’ve discovered that the best cybersex is to be had by going along with the person you are playing with. Unless it takes you somewhere that is a turn-off, if you build on whatever comes from the other person, it can be very arousing. I allowed myself to forget all my inhibitions and commit to the scene. It really felt like I was having sex with another man. It was like an interactive erotic story and I was stroking myself like crazy as we both reached our virtual peak.
My typing went south, grammar went out of the window, spelling dropped to second-grade level. But the sex was all grown up.
A man had made me cum with his words and I was hooked.
I became a regular in the chat rooms and found other partners. Some were less attentive than others; some had fantasies that didn’t match mine. I soon learned which men would be fun to play with and which ones were clumsy, needy or just plain dull.
Mark was none of those things. He was smart, enthusiastic and inventive. We played together regularly and discovered the roles we most enjoyed in our time together. He was top and I was bottom. As time passed, the top and bottom roles evolved into daddy and teen and then daddy and sissy. In our minds, I was his girlfriend. I was Bobbi when we were together.
While I would chat with other men and women online and was often the more dominant partner, with Mark I became more and more subservient. I loved when he would cyber-fuck me or when I would drop to my knees and suck his cock.
When we were online looking to play and the other was away, we would leave little messages for each other. I would get hard just from seeing that Mark had left me a note. It was exciting to think that another man was hot for me.
I loved to tease him with brief de***********ions of what I wanted to do with him. Precum would drool from my cock as I wrote him my little scenarios. He brought out all the latent desires I had kept so carefully suppressed all my life. I felt completely free to tell him things I had never said to anyone else. He shared his innermost thoughts with me too.
After a while, we weren’t cyber fucking. It was more like love-making.
My fantasies were so sharply defined when we were together and we meshed so well. We would frequently find ourselves writing almost the same thing at the same time during our chats. We were imagining the same action and knew what each other would want to happen next.
We also talked about other things when we were together and found ourselves to be on the same wavelength about a lot of life in general. I really started to like Mark. I dreamed about meeting him in real life, but we were both married and lived on opposite ends of the country.
One day, I got picked to run a booth at a business convention in Las Vegas. I mentioned it to Mark because I wouldn’t be around for a week. Mark’s reply was a jolt. By coincidence or fate, he was going to be in Vegas for his own reasons at the same time.
So now we faced a turning point. For all the fantasies, neither of us ever expected that we might have an opportunity for meeting in the flesh. What would we do? I joked that we would have to put up or shut up, not knowing how he would reply.
Mark’s response was non-committal. It wasn’t an invitation, but it wasn’t a refusal. We were dancing around the subject.
I recognized where I was. In my youth, I had been in situations where I might have gone with a man and had always been too inhibited.
After the fact, the idea had always excited me. I lost count of the number of times I had masturbated, thinking about what might have happened.
I had regretted these missed opportunities to experiment ever since then and had promised myself that, if another chance ever came up, I would not be so timid.
Yet here I was again: not grabbing the bull by the horns, as it were.
So I steeled myself and told Mark that I really did want to meet up and live out some of the things we had talked about that made us both so excited. I think Mark was in a similar frame of mind and had been waiting for me to decide for him. He replied that he was into it, as well.
We made an appointment. A date. I pushed the guilt and inhibitions aside and allowed myself to be thrilled by the thought of going on a date with a man. We decided to meet in the bar of my hotel and see where things might go. No pressure.
I didn’t know how far we might go, sexually. I wasn’t sure if, when pretend became reality, that I would go through with it at all… but I wanted to be ready. So, I primped and preened and made myself clean inside and out as I prepared for our first meeting.
My hotel had a lingerie store in their arcade and, on a whim, I had purchased a pair of silk ‘boy shorts’ panties and matching slip. I had done some research online and figured out the equivalent ladies’ size to my male measurements, so I was able to ask for a ’14’ and make it seem like it was for my wife.
I had never worn ladies’ clothes before but if our date led anywhere I was going to be as girlie as possible. That role was the distillation of our fantasy sessions. Mark liked it and it excited me very much. Now, as I readied myself for our first meeting, I was about to wear ladies’ clothes for the first time.
I slipped the sexy panties up over my soft, pale buttocks and enjoyed the silky feel as they cupped and held my freshly shaven cock and balls. I pulled up my jeans and enjoyed how the panties moved frictionless and free under them.
Every movement gave me a little rub against my ass or genitals. When I pulled on the skimpy slip with string shoulder-straps, put a shirt over it, and felt that same sensation over much more of my body, a shiver ran through me.
And now I was going out in them. I was going out in girl’s panties and a slip… to meet a man. I was tremendously excited.
Then the moment had arrived. I left my room to go on my date with Mark.
I felt very obvious as I stepped out of the elevator and crossed the lobby to the bar, as though everyone could see the lingerie I was wearing. I was so conflicted. I felt ashamed to be such an obvious sissy and yet thrilled at the same time.
Of course, my undergarments weren’t obvious at all and I didn’t feel such a sissy that I ordered a Cosmo at the bar. I sat with a manly beer and watched the Golden Knights on the TV. Beer and hockey.
Macho. As. Fuck.
Macho, until I saw Mark enter the bar. Then all the feelings of being with Mark online came to the surface. I felt coquettish and meek and had to stop myself from fawning over him as he came over and took the stool next to me.
“So, we meet at last!” he said in a Bond-villain kind of voice.
I laughed and offered to buy him a drink.
“No thanks, I’m good.” Then he leaned down and whispered in my ear,
“Take me to your room… I don’t want to wait, Bobbi.”
His urgency was hot. He wanted to get me alone.
“Oh, Bobbi! Yes!” I was thrilled to be called by my sissy name in real life for the first time.
I quickly dropped some cash for my drink and a tip and led Mark to the elevator bank. There were several other passengers going up. We stood next to each other at the back of the car in silence.
Then I felt the back of Mark’s hand touching against my thigh.
I turned away from him slightly and his palm cupped the cheek of my ass. I felt my boner growing. Tight within my panties. Trapped inside my jeans. This was happening. A man was touching me. I was into it.
We were the only people to get out at my floor. Mark walked along with me to my room. My hand brushed against his… like when a teen boy is walking with a girl he likes but doesn’t dare to actually try and hold her hand. It was thrilling.
Whatever misgivings I might have had in the past were gone. I was fully committed to this adventure and to finding out what might happen next.
As we walked on, his hand moved to my ass. I swished my hips a little. Encouraging him. Enticing him, I hoped.
I had an erection trapped in my panties and ached for him to touch it.
I didn’t have to wait long. He stood behind me as I fumbled with the card key for my room. I dropped it and bent down to retrieve it. He put his hands on my hips and humped against my ass. As I straightened up, one hand went to the front and he rubbed my hard cock through my jeans.
The moment my room door closed, he pressed me against the wall and put his lips onto mine. I felt his hand reach down between us and he rubbed my crotch. My precum was leaking and wetting my underwear.
I moaned. My arms went around his neck and I kissed him back harder. My body started making decisions for me. I moved my hips forward. There was no mistaking my message. I wanted him. I wanted him to make love to me.
He moved his thigh between mine and opened my legs. Grinding against me. Humping his cock against mine.
I broke away from his kisses. “Come to my bed, Mark.”
I pulled back the top covers and laid out a towel in the middle of the fresh king sheet. I didn’t want to wait another moment. I quickly undressed to my silky lingerie and stood at the bed.
Mark approached me, still fully clothed. It made me feel thrillingly vulnerable. I wanted to feel this way. Dressed in girly underwear. With a man. He was going to become my lover. I was his girlie boy.
I never thought I could become so feminine, in my mind, at least. But Mark brought out my deepest desires. Desires I had kept hidden, even from myself. I was excited to be almost naked with a man. I was excited to be wearing lacy underwear. I was excited to know he was aroused by looking at me.
My hand reached down to his bulge and I felt him. Felt his arousal. He was hard. I was making this man hard and I had no shame about it. I was glad. I was going to give myself up to this man. This manly man. And he was making me be his girly lover.
I dropped to my knees in front of Mark. It was the most natural thing. I wanted to be there. Below him. Facing his crotch. He knew it.
He understood that I was shedding all my inhibitions. His hand gently rested on my head and I reached up to unbuckle his belt and unzip him.
I pulled his trousers down. He was wearing tight satin briefs. Not panties, but very sexy. His bulging cock was clearly outlined.
I touched him through the silky fabric, running my hand along the length of his shaft. It was hard and trapped and I couldn’t wait.
I reached up to his hips and tugged on the briefs. His cock was stretched down for a moment and then sprang free, almost hitting me as it bounced up.
I slid Mark’s underwear down and he stepped out of everything so that he was naked from the waist. I reached out to touch him for the first time.
My first cock. In my hand. It felt so right.
I stroked Mark’s shaft for a few moments and then felt his hand on my head guiding me towards him. I quickly opened my lips, licked them and took his cock into my mouth.
‘Oh, Mark’, I was thinking, ‘finally!’
I was on my knees sucking off a man. Not just any man, but Mark. Someone I had come to like and admire.
Until this moment I hadn’t admitted to myself that it was a crush! As real and passionate as any I had had for a girl in my teens.
Except, instead of desiring to possess, I was desiring to BE possessed. I wanted Mark to want me. And I was so happy that he seemed to.
His gentle words of encouragement, his tender caress as I knelt between his thighs and sucked him off made me feel complete in my role.
He knew I had never been with a man before and was as kind and patient as he could be. I took my time. My tongue traced the head of his erect penis. I pulled my mouth off and licked and kissed my way from the head to his balls.
Worshiping his beautiful penis. Stroking and kissing and sucking. Loving it. Yet still wanting more, I realized.
Mark pulled on the string shoulder straps of my silk vest. I raised my arms and felt it slip up over my body and off. Now I was on my knees with a man, wearing nothing but tiny feminine panties.
To the point of our meeting, I had not known how far I would want to go. Now I did. I wanted to go all the way. I wanted him to fuck me. To stick his cock into me and fuck me like a girl. I had taken his cock deep into my mouth as I had these thoughts and made my decision.
Now I moved my head faster and sucked him harder. My hands were on his bare buttocks and his were on my head. Mark moved his hips, fucking my mouth.
I reached down and slid my hand into my panties. Rubbing myself, I could feel how much precum had leaked from my cock as I sucked Mark. It had made my panties wet. I grasped my shaft and began stroking myself as I continued sucking him. My foreskin slid easily back and forth over the head of my erect penis.
Mark felt the movement and gently pulled me to my feet. My mouth reluctantly left his glorious cock, but Mark’s lips were back on mine and he rubbed me through the sheer fabric of my panties. He held me close in one strong arm and I felt his other hand tugging down my underwear. He exposed my ass.
Everything we were doing was a first for me. Everything, another step toward the ultimate submission to a man.
My arms were entwined around his neck. Kissing him with passion. Telling him with my movements that I was into whatever he proposed.
I was thrilled by the touch of his palm on my bare ass. I ground myself against him. We could feel our two cocks rubbing against each other, separated only by my thin undies until even they were tugged away. They slipped down my thighs and calves into delicate crumpled shackles. I stepped out of them, wanting to be sure I could spread my legs for him.
Now I was naked. Naked in the arms of a man. I helped Mark remove his shirt. My hands could touch his bare torso now, and feel his hairy chest. His pecs under my hands. I roamed over his body. Feeling his muscles. Everything reinforcing the illicitness of this episode. Man-on-man activity.
My cock slid along the length of Mark’s. He was longer and thicker and I felt even more in his thrall. Now both his hands were on my bare bottom. Cupping each cheek. Gently teasing them apart. Exposing my virgin asshole to the room.
I thought this was the moment. I was ready to lie back and spread my thighs. I was ready to feel Mark climb between them. I wanted it. I needed it. To feel him fuck me. I was tingling with anticipation.
But Mark slipped through my arms and down to his knees. He kissed me all the way. His lips brushed my neck and shoulders. Then, over my smooth chest, and he sucked on each nipple in turn. My legs were trembling. He moved lower and kissed all over my belly. My cock was throbbing. I clenched my buttocks. My cock twitched and I felt a surge of precum escape.
Mark saw and took me in his firm grip. His mouth was quickly over the head of my cock and he sucked and swallowed. Tasting me.
I looked down. Now my new lover was pleasuring me the same way I had just been doing him. I watched my hard shaft sliding between his lips. His caring, loving lips. He was making sure I felt as good as he felt himself.
My hands held his head as my cock moved in and out of his mouth. It felt so good. He did things with his tongue no girl had ever done.
His hands were back on my ass and now I felt his finger curl into the crack. A fingertip delicately grazed my anus. It was electric.
I held his head tighter. Thrust my hips. It was message enough, and Mark pressed. Just the tip of his finger entered me, and I came. There was no warning. I just ejaculated. Shuddering spasms. I moaned, tried to pull out. He held me tight. Held me so my cock couldn’t escape. I felt more and more hot cum shooting into Mark’s mouth and I felt him swallowing.
Oh, man. Never before. Never like this. Never so good. The orgasm was almost too much to bear. My legs were weak. Mark sensed this and, with one hand raised to my chest, pushed me backwards. I sat down on the bed’s edge. My legs apart. Mark, still with my cock in his mouth. He knelt there, taking every last drop until he was sure I had finished.
I flopped backwards onto the bed. Mark’s mouth came away from my softening cock and he climbed up beside me. His lips came to my mouth and as we kissed again, he dribbled some of my own cum into my mouth that he had saved.
I reached to the bedside cabinet and grabbed a tube of lube. There was no stopping now. Mark took it and squeezed some onto his fingers.
My legs were still wide apart and he quickly found his target. Where his fingertip had been a minute before, he now slipped in his entire finger. I moaned. He was kissing me and penetrating my ass.
A man. Fingering my ass.
He slipped in and out slowly but insistently. I had already had bigger things in my ass, but this was more exciting. To finally be doing it with another man.
Not just another man.. with Mark! My crush. My lover. My online boyfriend.
After a few minutes of deep kissing and deep fingering, Mark added a second finger. He moved faster, too. I felt him separating his fingers inside my anus. Stretching me. He added a third finger. I whimpered a little then. It wasn’t quite painful, but it wasn’t comfortable. It seemed to burn.
My sphincter muscle was stretching beyond where I had ever gone.
With three fingers ramming into my ass and Mark’s tongue thrusting into my mouth, I never felt so submissive.
I gave into it. I relinquished my manhood. I was Mark’s to use now. I wanted him to take me.
My hand pressed gently on Mark’s flank, encouraging him to move between my legs. He reacted immediately. He was ready. He wanted me. I was thrilled that I excited him. His fingers slipped out of my ass and he moved between my legs. I lay on the bed below him and looked up into his gentle eyes as he guided the head of his fat cock to my waiting hole.
“I’m going to fuck you, Bobbi…”
“I’m ready, lover man,” I told him.
I felt the tip of his penis touching my anus. A man was about to penetrate me. It was the ultimate turning point in my sexuality. He was going to make me into a sissy faggot and I was desperate for it to happen now.
I hunched my ass up. He moved his hips down. His cock went into my ass.
This was it. This was the moment. I was being fucked up the ass by a man. I was his sissy slut now. His girly-boy. I felt him slide deeper into me. I held him in my arms now and pulled him down onto me. Feeling him fuck me deeper until he was all the way in.
“Oh, Mark!”
“Oh, Bobbi! Oh, my little girly-boy!”
His weight was on me now, as he bucked his hips and maintained a steady rhythm. In and out of my eager ass. The preparation, the lube, the fingers… had all made this into a wondrous time.
There was discomfort. I felt stretched. It burned, like a pulled muscle… which is what it was. But it made my body tingle and my mind reel.
My cock shriveled. It shrank for some reason, even while I was as excited as I had ever been.
I moved a hand to my cock and balls and covered them with my palm. Pulling them up and out of the way. They were irrelevant at this moment. My boy-pussy was the only thing that counted. I was all-girl for now.
Mark leaned down and kissed me. Fucking his new girlfriend and thrusting that firm tongue deep into my mouth. His weight on his knees and forearms. He gripped my shoulders and pulled himself into me.
I just lay there, taking it. A sissy now. Taking cock in my ass. Giving my body up. Loving how it felt to be fucked by a manly man.
My legs found their way to the crooks of his elbows. My feet in the air on either side of his humping, thrusting torso. My arms were around his body. Around his back. Clasping him to me. My hands moved up and down his bare skin. I found his ass and pulled him into me. Feeling his buttocks clench and relax each time his wonderful cock plumbed the depths.
My eyes were on his.
“Are you okay?” he asked.
“Yes… yes… yes…” I told him, in time with his cock piston.
“I love your ass, Bobbi.”
“I love your cock, Mark. I love how this feels. How it makes me feel.”
“I’m close, lover…”
I humped my hips up to meet him. “Yes, I want it. Cum, Mark. Cum in my ass. Give me your cum.”
He moved faster. Really driving into me. Faster and harder…
“OHHH god, yeah yeah yeh yeh mmmph yeah, here it comes…”
And then… he froze. He was grinding himself into me and I watched his face as he climaxed.
I looked up at him as he pumped his seed into my girly ass.
Being his slut, his bitch, his sissy cum slut.
He gritted his teeth, squeezed his eyes shut and grunted with each buck of his hips. I counted seven shots before it began to subside.
Still, he remained deep in me. Jerking and shuddering. Cumming in my ass.
I was overjoyed. Different thoughts meaning the same thing ran through my head. I had made Mark cum. He had found me so exciting. My ass around his cock had brought him off. A man had fucked me to completion. There was cum in my ass. I could feel how wide my smile was. It was stretching my face.
Mark dropped from taking his weight on his hands to his elbows. He collapsed onto me. His mouth was at my ear. I felt his hot breath as he whispered loving words.
“So good, my sissy lover. So good. I never thought I’d like this so much.”
I hugged him and replied that I hadn’t imagined how good he would make me feel.
His cock began to shrink and I felt him pull out. Cum seeped out of my ass.
I felt that stretched hole closing slowly. Mark climbed out from between my thighs and I was able to lower my legs and close them a little. Being so widely spread for so long had been quite a workout.
He lay next to me with an arm under my shoulders. I nestled into his chest. Mark idly ran his fingers up and down my belly and chest and whispered sweet nothings into my ear.
“You’re so sexy, Bobbi. You turn me on. I love your smooth skin. Your slim figure. Your sexy ass.”
He nuzzled my earlobe. Butterfly kisses down to the nape of my neck as I turned away from him slightly. We were spooning. His lips brushed against my neck and shoulders. His semi-hard dick rubbed the cheeks of my bottom.
His hand moved down to my cock. I felt it stirring. He was bringing me to another erection. His hand went around my stiffening shaft. He sat up onto one elbow so he could watch himself stroking me. I rolled back onto my back and he began to jerk me off while he kept on with his sweet compliments
I lay there with my eyes closed. Limiting my sensory input to his loving words and touch. Feeling that burning, stretched sensation in my ass and that big fist around my cock.
A gentle handjob after the rigorous shafting I’d just taken was perfect. Even though I’d stayed soft while he fucked me, precum had been steadily dribbling and I felt my foreskin slipping easily up and down again.
I moved a hand and put it on Mark’s, giving him input as to how fast he should move his hand and how hard to grip. I moaned in pleasure as he hit the perfect combination and let him bring me off.
Cum shot up. I felt it landing on my chest. Then I felt Mark’s lips around my cock again as he took the remainder of my orgasm directly into his mouth.
My hand was on the back of his head. My fingers ran through his hair.
My climax ended and Mark came back up to me. His lips found mine. We shared my cum. Then he lay down beside me. We were two naked men staring up at my hotel room ceiling, reveling in the pleasure of their first sexual encounter.