Valentine's Day Date Dream Cum True

Story Info
Toy Boy "Army Bear" get what he wants from his Ts Mistress.
5.1k words
4.67
26.9k
9
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

On a beautiful, cold Saturday morning in Connecticut, I woke up tired and in a bad mood. I cleaned my room, fed the dog, and decided to take him for a walk to go to the store to get some smokes. As I walked, I was thinking to myself "Fuck. No Valentine's Date for me this year."

I could not believe I was still alone after two years, my ex boyfriend cheated on me and I didn't want to let no one hurt me again. I am great lover. I am clean, a great cook, and a home body. What's wrong with guys these days? They just want to get laid and that's it. I am tired of them!! I am a good girl now and not as wild as before but tired of being alone. But that has lead to my life being so boring for the last 2 years. I walked my dog "Greco" for a while and went back to my place, which was almost empty.

I was planning to move in with a friend for a while before I moved back to my home next month Home to "my Puerto Rico!" I went upstairs to my brother's apartment to check my email. As always while reading emails, my IM pops up. It was this guy I met 2 months before online.

"Army Bear" Chad Lee and I met thru a site under the transgender looking for guys section on December 16, 2008, but I met few guys before from there and I knew what it was all about. He contacted me thru the site email and I replied with my email address, which lead to him sending me his pictures. We exchanged some basic information thru a few emails and we both exchanged IM nick names. We finally met on the IM and chatted for a while getting to know each other. We talked about regular everyday stuff and eventually got into some sexual content.

After our first online conversation, I didn't hear from him again. Occasionally I saw him online but I didn't bother to contact him. Sometimes he said "hi" and exchanged few words but that was it. I had forgotten who he was already, but I knew we chatted before. I do have manners and I never ignored his "hi".

That Valentine's Day, Army Bear pops up on my IM screen saying "hi". Being Valentines Day and me being bored, I knew that this time was going to be different. We chatted for a few hours and during the conversation he asked me out a few times. But I wasn't that sure. I thought he was another freaky, online player dude. I asked him for his pictures at the last minute before I was ready to log off and he sent them to me.

He kept asking me out while I checked him out and I thought, "I do remember him. I think I still have his pictures somewhere." I checked the pictures folder from guys I liked and I found him. He had sent me those pictures 2 months before. I said to myself, if he is for real...I am going to have a hot Valentines Day boy toy to play with.

He was cute, handsome, hot and sexy. I didn't remember what he was into sexually, except that he was a curious panty boy. I got all excited while he was strongly trying to convince me to meet. Finally, I couldn't resist his offer and I agreed to meet! I told him to meet me at my place, in an hour and a half. I ran to get all my stuff together since I never expected to have a date on that Valentine's Day.

I jumped in the shower and got all dressed up for him: a short black, velvet dress with a low v neck, my cleavage showing nicely. A white brassier with matching thong, tight high black stockings, knee high, white and black striped winter stockings with my four inches winter boots heels. I was looking hot!!

He was running 15 minutes late because he got lost, but he had the courtesy to call to tell me. When he showed up, I went out to meet him and as we introduced each other. He kissed me on my cheek, which was very sweet. He came in and when he saw me without my long winter long coat ....

He said, "wow, you look sexy."

"Thanks baby, you're not too bad yourself. If you don't mind, we are going out. I know a bar where we can go, have a few drinks, get to know each other better and then come back home in a few hours." I said.

He smiled and agreed staring at me. I knew right then he was submissive.

I was lucky with this 27 yrs old jewel who found me. He was a handsome young guy, who went into the bar holding my hand. I loved it!!! His killer smile and his cologne "Brooks Brothers Men by Brooks Brother " ,drove me crazy from beginning. I couldn't resist that smell of his body. He opened the door for me and grabbed my hand again while the whole bar stared at us.

They were shocked to see me since it had been more than 1 month since I had visited the bar. And I was looking hot and this time with a fresh meat charming boy toy. I said "hi" to a few ex co-worker female friends and I introduced him to them. We sat in semi dark corner of the bar and he ordered our drinks.

We started to get to know each other better face to face, not from behind a computer screen. We couldn't stop staring at each other; there was a lot of eye contact between us. My seductive eyes were penetrating his and his beautiful eyes were melting me. The chemistry was incredible. My heart was beating so fast, but I wasn't the only one; you could see from far away how nervous and excited he was.

The drinks broke the ice and I started seducing him! I knew he wanted me to take the lead, so I started rubbing my foot against his crotch. He was already hard!! I kept looking into his eyes, taking a sip of my beer while talking to him, rubbing his big cock with my foot. His beautiful eyes were shining, he couldn't stop smiling at me with his innocent face and I loved it. But I thought to myself, "he isn't going to fool me, I know he isn't that innocent ."

I looked around the full bar of straight people. They were shocked and couldn't stop staring at us. That just got me even more excited. I turned around and looked at him...

"Do you like that baby?"

He looked at me with shy smiley face and mumbled in a light tone of voice

"Yes".

"I can't hear you, honey," I replied.

I stood up getting closer to him. I rubbed my body against his as I got closer. Raisin my left leg over his wide open legs, I pushed my knee to his crotch. He was rock hard! I grabbed his chin and seductively, staring at his tiny, shiny eyes.

"What did you say again?"

He was so nervous. His body shook with so much excitement that he couldn't even breath, much less answer my question.

I whisper in his ear, "Don't be nervous baby, I don't bite. Do you like this?"

He mumbled, "yes".

"Did you just said ,yes?"

I blew a hot breath from my lips into his ear. That drove him nuts! His eyes were closed tight as he twisted his head around in slow motion, enjoying my seduction. My tongue started licking his ear while my knee was rubbing his hard cock. I found his first sensitive body part, his ear. He started a low moaning and his hips pushed his cock harder against my knee.

"Oh yeah papi, I know you love it!"

I started to stand up with my knee still on his crotch. He pushed his two hands slowly under my skirt, grabbing my ass and holding my thong bulge. I got closer, rubbing my crotch against his hand and over his body, while he started squeezing my butt. I was so scared to get hard but I was horny as hell!

There were all these straight people watching me seduce my toy boy, and that just turned me on even more! In my seven years of bartending in a lifestyle bar, I had never experienced this with any guy. They all knew I was a T-girl but I had never made out so openly in a straight bar.

I was hot (and by his bulge I could tell he was very excited) and licked and kissed his ear and neck for a few long minutes. I loved how he was enjoying it, and how he was exciting me by playing with my excited semi-hard clit. I pulled my knee away from his crotch and sat over his legs, looking at him ....I knew he wanted to go back to my place, but not yet. "I am going drive him crazy," I thought to myself.

Lying against him and close to his mouth I told him...

"I am so happy you are my Valentines Date. Tonight is going to be special for both of us. We are going to have fun! Are you ready baby?"

"Yes, oh yes," he said.

I gently touched his face with my hands and we started kissing with passion in front of everyone. We were so close to each other, it felt like we had became one. Rubbing my crotch against his stomach and bulge, I moved my hips all over him. His two hands were under my dress all around my butt, squeezing it. It felt SO GOOD!

We kissed with passion and lust; holding his tiny face between my hands, kissing him deeply, our tongues embraced all over our hot and wet mouths. I licked his lips enjoying how soft and tender they were. I went back to licking his neck and ears, while he buried his face in my cleavage, smelling and licking. Oh, yes, it felt so good.....

Caressing his face, his ears, his hair; I put my hands under his shirt, touching his smooth, hot chest.

I whispered in his ear, "We better slow down or we are going end up fucking right here."

He agreed, but we couldn't take our hands from each other. It took around 30 to 45 minutes for us to finally stop; we were so hot already!

I cleaned my lipstick mess (and cleaned his too). I stuck my finger inside his mouth, sliding it in and out. Then I put it in my own mouth to show him my oral talents. He was licking his lips and couldn't stop smiling. I knew he was loving it!

He was so fucking hot; I couldn't resist this young 100 % grade A meat. The bar was getting kind of empty as we sat finishing our drinks. "I got a surprise for you waiting at home", I told him and we got up and left the bar. Once home, I told him to get comfy while I changed into something more comfortable. I found an even sexier outfit and got another drink for us. I came back to chat a little more. While smoking a cigarette....

"Let's get busy baby!" I whispered to him.

I got closer and said, "You got to many clothes on , let me help you get you naked." First his shirt fell to the floor, then his belt. I pulled down his pants and then his young, hard cock popped out. He was dripping pre-cum and oh so hard already.

"It is all your fault, you got me so hot!"

I got up and told him to lay on my bed while I turned down the lights. Leaving my room just with a dim color light atmosphere, I tuned the radio with some romantic music, lit a candle and incense, and lit another cigarette. I took out a sexy black thong, matching bra and tight, high stockings and handed them to him.

"Honey, you are going to be my bitch tonight!"

I dressed him like the slut he was. I knew he liked to wear women's clothes, but he never thought I would make him do it. He was standing there staring at me looking slutty as I got in front of him while wearing my sexy outfit and took him in my arms while I started kissing him again. He grabbed me around my waist and we started making out. I kissed him deeply, playing with our tongues. Sticking our hot and wet tongues deep inside each other's throats while he caressed my back and I caressed his. I grabbed his head and continued talking in his ear softly while licking it deep inside.

"Do you like this, are you excited papi?"

"Yes, yes, very much, you know what I like."

I kept playing with his ear and neck and then went back to his mouth... when he suddenly grabbed my hard cock in his hand and started playing with it.

I licked his mouth over and over, tasting his lips, while he did the same to me.

"You like my throbbing cock, don't you baby? You want to taste it, don't you Slut?"

"Oh yes baby!!!" He replied back with a soft voice.

I started playing with his hard cock; damn he was so fucking hard. His swollen cock was dripping pre-cum. With one hand I played with his nipple, while with the other I played with his tool. My hot mouth went to his hard nipples; nibbling on them back and forth, licking, biting, sucking them while he stood there.

I went down his stomach, getting on my knees while watching him become excited all over. I grabbed his hard fuck tool and started licking his long, tasty cock and played with his balls at the same time. I caressed his smooth, shaved crotch, licked his balls and stroked his hard cock while my hot tongue ran back and forth from his cock base to the head, getting my hot mouth all wet. I went down to his balls and started licking them, sucking them into my mouth one by one, then both at the same time, while I continued playing with his throbbing cock and squeezing his tender, soft bubble butt.

I knew he wanted me to suck on his dick, but I didn't. I was just teasing him, wanting to drive him nuts first. I decided to do my best after a few minutes of teasing. I grabbed his hard cock and started sucking the tip.

"Ooh that feels so good! Yes!!"

My mouth enveloped his cock with my wet lips, while I started taking inch by inch of it. Sucking and tonguing in and out, deep-throating his hard tool. I grabbed his butt, squeezing it hard, causing his legs to shake. I pulled and pushed his body against my face back and forth; sucking, licking , deep-throating his manhood for a few long minutes, making him fuck my hot mouth till I decided it was enough. That's only a taste of how good I suck cock.

I got up and we kissed again. He was sweating already and so excited.

"Now it's your turn baby, get on your knees and get busy, show me what you got!"

He got on his knees and he started tasting my 7 inch hard-on. It felt so good getting head from this young slut. I held his head with my hands and started fucking his mouth in slow motion. He grabbed my hips and pulled me against his mouth for me to fuck his face back and forth. He sucked me so fucking good, that there was no doubt he knew what he was doing. I was enjoying my boy toy slut enjoying my swollen member; slurping on it, playing with my nuts till I couldn't take it anymore, I stopped him.

"Come here, slut," I said while grabbing him under his arm. "I got another surprise for you!!!!"

I blindfolded him, ordered him to lay down on the table, and tied him up from the ceiling hooks, leaving just 1 leg un-tied. He was shivering in fear or excitement (or maybe both, hehe), but I made him felt safe; talking to him, teasing him with a tickle feather all across his upper body. Tickling his nipples turned him on a lot! I stopped tickling and kissed him, sticking my hot tongue into his mouth and licked his lips. I moved away and he tried to reach my lips with his tongue, but he couldn't move. I moved to his ear, asking him......

"Are you excited bitch?

He moaned, "Yes."

I continued running my tongue down his neck and chest, stopping at his hard nipples to nibble one, while I twitched the other one.

He moaned, "ahhhhhhhh," thrashing around with no way to touch or stop me.

I kept tickling him; moving down his belly, his legs, his feet, getting between his legs and teasing his hard cock in his panties. His inner thighs were shivering from the onslaught of the feather. I dropped to my knees and pulled his panties to the side, letting his cum filled balls bounce in front of my eyes. Pushing back his untied leg, I moved in and my hot mouth started licking his inner thighs, while his balls were all around my face begging me to take care of them.

Spreading his butt cheeks, I buried my face in his ass and tongue-fucked his asshole as I played with my soft cock. He moaned like a cheap slut when I slid my tongue deep inside his ass. I licked it for a few long minutes while he was moaning like the little slut he is. I sucked his balls while I pulled out his hard cock, dripping pre-cum already, and I filled my mouth with his big, juicy balls full of cum; sucking and licking them while I rubbed his hard on up and down. I moved up to reach his cock to put it in my hot mouth. I held it tight and started sucking it with no mercy. My mouth was craving for his big, fat cock deep inside my mouth. I gagged a few times, but I did deep throat him a lot. My face was covered with my own saliva; sucking and deep-throating his hard , fucking, slutty ,tool; licking his balls and rimming his asshole; moving up and down on his entire crotch area.

I took a break to light a cigarette while I kept seducing my lil slut who was totally under my control. I stepped in front of his face letting him smell my balls. I gave him a chance to lick them, while I kept teasing him with a stick, hitting him with soft strokes all over his torso. I slid my panties to the side and I let him take the head of my cock between his lips and suck on the tip of it. He sucked it in and out until it got nice, and hard. I started to fuck his mouth in a nice, slow motion, with a few hard thrusts mixed in.

He took inch by inch of my then rock hard cock. I ended up moving on top of him, holding myself against the desk. He gagged each time my hot cock slid down his throat; my balls slapping his forehead. I held his stiff pre-cum coated cock in my mouth; sucking and tasting his pre-cum, slurping on it, going up and down, licking and sucking while he did the same to mines. He sucked my balls as I massaged his cock; stroking it back and forth. "Gag on that fucking cock bitch," I though, getting up and untying him.

I told him to get up and, "suck me bitch." He dropped to his knees and pulled down my panties, leaving my cock bouncing in front of his face. He sucked it so good, licking my balls at same time, that he gagged himself on it. Feeling my throbbing cock head hitting the back of his throat was amazing! He sucked my balls as he massaged my hard cock. He started fingering my ass as he deep-throated my entire tool. He pulled me onto his face and had me fuck his throat as he rammed my asshole with his finger. "Oh gosh!, let's go to bed slut."

I laid on the bed, while he buried his face between my legs, sucking my throbbing cock. He licked my balls as he massaged my hard clit. Then he moved his face between my ass cheeks; spreading them, he started eating me over and over.

"Ohhhhhhhhhhh, yes! I love that slut! Fuck my ass with your tongue, go deeper dammit, fuck me with that wet, hot tongue!" It felt so good!

He stayed eating and licking me for a few minutes till I decided to 69. It was awesome! We wrapped our wet lips around our hot, hard cocks. He was on top of me as we sucked our cocks over and over; up, down and all around, slurping on them, licking our balls. He pulled my legs up and tongue-fucked my ass while I spread his butt cheeks and buried my face into his ass; eating his asshole with furry, as he did the same with me.

"Oh yes! O yes! Oh gosh," we both moaned with pleasure.

Suddenly he stopped sucking me and he sat on my face, oh lord! I couldn't breathe but his ass felt so good, I kept munching in it. I spit in his asshole a few times, licking it and spreading his ass wider; sticking my tongue, fucking his asshole with it.

He moaned while stroking his cock, "Oh, that feels so good ma'am, oh yes!!"

His throbbing cock was pouring pre-cum all over my stomach, while he stroked my hard cock. I slapped his butt as soon he buried his face in my ass again.

"Oh yeah slut, lick my hot ass, oh, oh," I moaned!

I sucked him with the likes that he had never been sucked before! I was so fucking horny! I sucked, deep-throated, and licked his balls over and over.

I rammed my finger in his ass while sucking his hard cock while he did the same to me.

"Oh yeah, oh my gosh, it's been 2 hours like this, I can't take it anymore, I m going to get your ass ready for me, baby," I thought.

I moved from under him and I ordered him to laid down on his back on the bed. As I got on top of him, we were kissing each other, licking each other's lips, sticking our tongues deep inside each other's throats. I kept licking his neck, ears, all over his head. He was very excited! My bitch was enjoying every step of my game. I felt my butt all wet with his pre-cum. It felt so hot!

I moved down to lightly pinched his nipples, licking and softly biting them; running my hot, wet tongue down his chest, belly, his smooth, shaved crotch, inner thighs, balls and cock. Sucking him like the good cocksucker I am. Watching him shivering , licking his lips and enjoying every movement of my hot lips. "Get ready slut. I am going to make you my bitch now!" I jumped from the bed to get condoms and lube. He was already getting his ass lubed with anal-ease when I turned around. That fucking boy toy slut was prepared for me. He did want me to fuck his brains out. "You won't forget our first encounter bitch" I thought to myself.

12