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Sissy Veronica’s First Time

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This story contains a cross-dressing guy sucking the cock of another guy — if that’s not what you’re looking for, please move along.


I had met ‘Sissy Veronica’ online, in a roundabout way. Turns out we were both married men with bisexual urges that we hadn’t yet acted on. We were both on a swingers’ site as couples, and while trying to work out a meet between us two couples, it became increasingly apparent that our wives weren’t ready to play. We continued to exchange emails, though, and occasionally share links to various porn sites that we both liked. In the course of these emails, it came out that we both enjoyed wearing panties and we had both fantasized about sucking cock. Veronica was more submissive, though, and wanted me to ‘train’ her in the art of cock sucking (something I had only enjoyed vicariously through porn, but what the heck!). One thing led to another, and after a lengthy exchange of emails, we decided to meet one day.

Veronica’s wife worked during the day, and Veronica worked at night. I had a very flexible schedule, and we set up a meeting at Veronica’s house one morning after Veronica’s wife had gone to work. Veronica got dressed in some sissy gear before I got there, and greeted me at the door in cotton panties with red and pink hearts, and a bra that matched the panties. Her little clitty was already quite excited when she opened the door, and could be seen straining against the panties, and leaking some pre-cum onto the cloth of the panties.

I immediately took charge of the situation. “Well done, Veronica. You’ve prepared yourself well,” I said.

“Thank you, sir. I was hoping that you’d like this outfit. It’s one of my favorites,” Veronica said.

“I think it will be one of my favorites, too, after I see how you perform. Let’s get started,” I said.

We were in the living room, but I said “Let’s go into your bedroom. I want to see your other panties and any toys that you might have.”

“Yes, sir,” Veronica said meekly.

She escorted me to the bedroom, wiggling her pantied ass as she walked, and when we arrived I told her to kneel near the foot of the bed. “Now show me where you keep your panties and your toys,” I said.

Veronica pointed to a dresser, and indicated the top drawer. I opened it, and there were a plethora of pretty panties lying loosely in the drawer.

“Those are my wife’s panties,” said Veronica. “I wear some of them when she’s not home.”

“They’re very nice,” I said, “Maybe you can model some others for me later. Now, where are your toys?”

“On the top shelf of that closet, in a cardboard box,” Veronica said, indicating a closed door in the room.

I went to the closet, found the box, and opened it. There were several vibrators, a smallish butt plug, some straps with velcro for restraint, and a lifelike dildo with a suction cup base.

“Well, this is a nice assortment, though limited. But it does have the one item that is absolutely essential for your training. Do you know what that is, Veronica?”

“No, sir,” she said meekly, though her blush and tremulous voice said she knew very well the answer to my question.

“I think you do know. It’s the lifelike dildo that looks like an erect cock. And it’s got the suction cup base. I’ll bet you’ve used that before, haven’t you? When you were alone and dressing up in your wife’s panties? Be honest now, Veronica. Tell me how you’ve used the dildo.”

She was hesitant at first, and began slowly to describe how she’d used the dildo, but she rapidly warmed to the idea of talking Ümraniye Yabancı Escort freely about her games; “Well… sometimes when my wife is away and I’m horny, I put on her panties and admire myself in the mirror. I always like to see my cock pressing against the fabric and making a wet spot where I’m leaking. Then I started to put on her bras, too, and sometimes her stockings and garter belts. That always just got me more excited, and my cock would be even harder. Then I began to imagine what it must be like to be a girl, dressed up in such sexy things, and getting ready to serve a man with a big cock. When I remembered that my wife and I had bought a realistic dildo, I got it out and put it on the tile wall in the shower at the right height, and then I got down on my knees and started sucking it. It felt so good to have my mouth full of cock, and to be dressed up like a girl, and to just let myself give in to the sensations of being on my knees, being used by such a big tool, and I wanted so badly for it to spurt cum in mouth, but of course it couldn’t.”

“That’s very interesting,” I said. “Tell me more. But don’t refer to your little clitty as a ‘cock.’ A cock is something that real men have — what you have just doesn’t measure up. It’s just a little girl clitty.”

“Yes, sir. My clitty. It really is little, but it always gets so hard when I suck the dildo. After a few times sucking the dildo on the shower wall, I remembered that we have a full-length mirror in the bedroom. Then I really wanted to see myself with my mouth full of cock. I stuck the dildo to the mirror so that I could watch myself suck it. And I did suck it, and watch myself, and imagine that it was a real cock, and I would stroke my little girl clitty while I was sucking. Sometimes I made a mess in my panties, I was so excited. And then I began to… not just suck it… but worship it. I would lick the length of it, and then kiss the tip. I would kiss the balls and suck them into my mouth. I would try to take the full length of it down my throat, but I never was able. I wanted more and more to feel a real man’s cock in my mouth so much, it was all I could think of sometimes.”

“That’s understandable,” I said, “that you want a real cock. I bet you watched a lot of porn, too.”

“Oh, yes, sir. I would watch sissy porn, where the sissy would worship a big cock, and I would try to improve my technique. I think I’m quite good, now, because of all my practice with the dildo, and all the porn I’ve watched, although I’ve never sucked a real cock. I think I’m ready to try a real cock, now, though. Please.”

“Well… We’ll see if you’re ready,” I said as I handed him the dildo. “Let’s see how you do with this.”

We went over the full-length mirror in the bedroom, and I had Veronica stick the dildo to the mirror. “You know what to do,” I said.

“Yes, sir,” said Veronica, and as she knelt before the mirror with the dildo protruding from it, she began to lick her lips, and then to kiss the tip of the dildo. She kissed the length of the dildo, adding licks to the underside, and she kissed the balls, too. As she worked her way back up the length of the shaft, she let her hand slip into her pretty panties and start to stroke her clitty. As she stroked herself, she began to suck on the head of the dildo, and to bob her head up and down on it. Soon she began making little whimpering noises, and I began to think that she was going to mess her panties.

“Alright. That’s enough for now. You really do have good technique. Would you like to try the real thing?” Ümraniye Yeni Escort I asked.

“Oh. Yes, please, sir. I want to suck a real cock so much,” Veronica said.

“Stop stroking your little clitty and put your hands behind your back for a minute,” I said. Veronica did as she was told. I walked over to her and stood in front of her, with my crotch inches from her face.

“Now, I want you follow my instructions, and do just as I tell you. Do you understand?”

“Yes, sir,” Veronica said.

“Good. Now use both hands to undo my belt buckle,” I said, “and then put your hands behind your back again.”

Veronica said nothing, but her hands shook as she reached up to undo my belt buckle. It wasn’t easy to get unfastened, but when she had it undone, she put her hands behind her back again.

“Good girl,” I said. “Now undo the button on my jeans.” Veronica reached up and undid the button.

“Very good. Now I want you to pull the zipper down, and start working my pants down.” Veronica’s hands shook again as she struggled a bit with the zipper, and then she began to use both hands to loosen my pants and let them fall to the floor.

“You’re doing very well. Do you like what you see?” I asked.

“Oh, yes sir. It looks like you’re already getting excited,” said Veronica.

“Indeed I am. Watching your mouth on the dildo made me think of what I’m going to have you do with my cock. But first, help me take my shoes, socks and pants off.” I steadied myself against the wall as Veronica untied my shoes and removed them, and then my socks, and finally she pulled my pants off and set them aside.

“All right, Veronica,” I said. “I want you to start kissing my cock through my underpants, all along the length, and also kiss my balls gently.”

“Yes, sir,” said Veronica, and she leaned in and started kissing my hardening cock through my underpants.

After a few minutes I said, “You’re doing a good job, Veronica. Now I want you to stop kissing my cock for a moment, and use both hands to take my underpants off.”

Veronica reached up and with trembling hands took the waistband of my underpants in her hands, and pulled them down my legs. My cock sprang free and waved lewdly in her face. Veronica looked at it, but she kept pulling my underpants down until they were all the way off.

“What do you think, Veronica? You’ve made me quite hard,” I said.

“It looks wonderful. May I please suck it?” Veronica asked.

“I want you to start kissing my balls, and slowly work your way up the shaft to the tip.” Veronica leaned in and started kissing my balls, and then she started working up the shaft with her soft, moist lips.

“That’s it,” I said. “You’re doing great. It’s going to be so hard when you take it in your mouth. But I want you to ask for it.”

“What?” said Veronica between licks and kisses, not quite understanding.

“Ask for my permission to suck my cock. Ask very nicely,” I said.

“May I suck your cock?” Veronica said.

“I think you can do better than that,” I said. “How much do you want it?”

“Please may I suck your cock, sir? Pretty please?” Veronica seemed distressed that she wasn’t allowed to suck my cock right away.

“OK,” I said. “But just the head.” I grabbed the shaft of my cock, leaving just the swollen head extended beyond my hand. I was dripping pre-cum already. “First kiss the pre-cum off.”

Veronica leaned in and kissed the very tip of my cock, where the pre-cum was forming a big drop. She sucked the clear liquid away lightly, and then Ümraniye Masaj Salonu began to suck the head in earnest.

“Such a good cocksucker, Veronica. I like the way you’re sucking the head. Would you like more in your mouth?” I asked.

“Oh, yes, please, sir,” Veronica said as she took a brief break from sucking the head of my cock. “Please may I suck as much of your cock into my mouth as I can, sir?”

“You’re such a good sissy, Veronica, and you’ve shown such enthusiasm for sucking the head of my cock that I am going to let you suck as much as you can,” I said.

Veronica smiled and said “Oh, thank you, sir,” and as she said so I released my cock and Veronica leaned forward to take it in her mouth. It felt wonderful as she bobbed her head up and down on my cock, alternating between long strokes and taking time to suck just the head. She would release it from her mouth from time to time to kiss the shaft and balls, and just admire its throbbing hardness. Then she would resume bobbing her head up and down on the hard shaft.

As I felt myself getting close to coming, I said “Stop for a minute, now, Veronica. I want to see your little clitty.”

Veronica reluctantly stopped sucking my cock, and leaned back a little.

“Stand up,” I said. Veronica stood, dressed in her panties and matching bra. The panties had a big bulge in them, and there was a growing wet spot where she was leaking pre-cum.

“Pull your panties down just below you balls, and I want you to jack off onto my cock,” I said.

She pulled the waistband of her panties down and tucked them beneath her balls. Her erection looked almost painful, and I didn’t think it would take long for her to cum.

“OK,” I said. “Start jacking yourself off. I want you to think about how you were just on your knees with my cock filling your mouth, and how much you wanted me to fill your mouth with cum.” As I talked, Veronica began to stroke her cock. “Get your cock very close to mine,” I said. “When you’re about to come, tell me, and aim your cock so your cum lands on my cock.”

Veronica was breathing heavily, and stroking her cock. After just a few minutes of stroking her cock inches from my own, she said, “I’m going to cum. Please, sir, can I shoot it on your cock?”

“Yes,” I said. “Shoot your cum onto the shaft of my cock.”

In just a few more moments, I saw the cum shooting from Veronica’s cock, and felt the warm wetness on the shaft of my cock.

“Good girl,” I said. “I think you know what to do.”

Without a word, Veronica fell back to her knees and began licking her cum from the shaft of my cock. When she had gotten all that she could by licking it clean, she took the length of it in her mouth again, and started sucking.

I grabbed her head with both hands and encouraged her to keep sucking. After another minute, I said, “That’s it, just hold still so I can fuck your mouth.” I pulled my cock from her mouth and said, “What do you want?”

“Oh, please, sir. Cum in my mouth. Please fill my mouth with your hot cum,” Veronica said.

“As you wish,” I said, and began to fuck her mouth with full strokes. In just a few moments more, I felt my cock swell, and Veronica moaned, and I began to pump spurt after spurt of come into her mouth. She whimpered and swallowed, but some of my cum escaped from the corner of her mouth.

After I had pumped the last bit of cum into her mouth, I pulled my cock from Veronica’s mouth and said, “That was very good, Veronica. Make sure you get the last drop from my cock.”

Veronica milked my cock with her hands as much as she could, and was rewarded by another drop of cum from my now softening cock. She licked it into her mouth, swallowed, and smiled.

“Thank you very much, sir. Your cum is wonderful.”

“I think you’ll have a chance to sample it again,” I said. Veronica continued smiling.

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