Sweet Baby 05

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Timmy's first date, and jizzing with his shemale mommy!
2.5k words
4.71
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Part 5 of the 10 part series

Updated 06/15/2023
Created 09/10/2022
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Sweet Baby

Born to be a Porn Princess!

by Mistress Tawny Suede

I do hope you are all enjoying the stories that I post! Please do leave feedback. Your comments help to encourage me to write more! And remember you can also leave comments on my older stories too! (you have checked out ALL of my stories, haven't you?) Tell me which ones you love and what you would like to see me write! - Love, Mistress Tawny!

Chapter Five - First Date!

When I awoke the next morning I discovered Mom had not come home. Her bed was empty.

I had a quick breakfast then took a shower and also cleaned my new belly piercing. It smarted a bit so I took one of the pain killers. I had removed all of my makeup the previous night before going to bed so my goth look was pretty much gone. However my hair was still jet black. I chose to wear darker clothing and even put on a small amount of darker lipstick - not enough to stand out but enough to make people wonder if it was there.

I again got both strange looks and compliments at school! Mostly compliments actually. The girls talked to me a bit more. Some of the guys who I did not normally hang out with found a moment to talk to me, and even Mr. Fillmore, my maths teacher, called me aside after class and said I looked nice. He said this while resting a hand on my shoulder then tousling my hair!

I was a bit concerned with what Mom might say about my changing appearance, but when I got home I found a note from her on the table. Apparently she had gotten some extra work. She had left a casserole warming in the oven and had left already. In fact she said she would definitely be gone overnight and might even be gone a couple of days!

Well, that made things a lot easier. After eating dinner I played video games on the big screen tv for awhile, but I was getting anxious about my date. I wondered what she would be like!

It was a good thing that I had plenty of time to get ready. It took me three attempts before I got my makeup to a point that I was satisfied with my goth look. From the new clothing that Roger had brought last night I chose the tightest black jeans and a black t-shirt with fake satanic symbols that come down only to my belly button, so that my piercing was visible. The shoes I chose were open toed with a small corked heel. Because they were open toed I painted my toe nails black, as well as my finger nails. I brushed a bit of gel through my hair and added some blue sparkles so that my hair shone in the right light.

I was barely ready at 9 when the door rang. When I answered, instead of a girl which I had expected, there was a boy there. Well, a young man really. I was startled, but I knew I was going to do everything that Mommy Jennifer asked of me. I picked up a small man purse that had been amongst the items Roger had left for me and we headed out to his car.

As we drove off, he told me his name was Troy and he thought I looked very nice. We drove for about twenty minutes and went into a restaurant with dim lighting. We just ordered burgers and fries and shakes. Over dinner I got a better look at Troy. For a boy he was cute! He was also wearing all black, but his hair was blonde, almost white, except for the deep black roots which fascinated me! Troy also had black nails and was wearing black lipstick. His mascara and eye liner were much better applied than my own feeble attempt.

We talked about video games and sports over dinner. When we got back to the car, he held the door open for me again just as if I was the girl on a date.

By then it was about 10:45 and he drove us another ten minutes to a club where the music was already very loud. It was a large club with at least a hundred people there and room for a lot more.

"Watch me and do as I do," Troy told me. "Mistress Jennifer wants you to learn from me!"

When we got into the club, we went to the bar and Troy ordered us a couple of fruity drinks. They didn't come with little umbrellas, but you would have expected them to. When he ordered, Troy used a lilting voice. When he turned around with the drinks he handed me one with a hand that I would have to describe as limp wristed. As we talked he waved his hands around. He was almost a pantomime gay.

"Timmy, darling, let's go dance!" We set our drinks down and he dragged me to the dance floor.

The beat was strong. The dance floor was dark but flashing lights strobed the crowd making everyone look like stop motion animation! Troy and I danced facing each other, but we were constantly bumping into other dancers. It did not take long before I started to glisten with sweat. As we gyrated I soon found myself facing and dancing with several other people, some were guys and some were gals.

The couples on the stage were mostly boy/girl, but there were several pairs of same sex couples dancing with each other, some quite closely. Hands found my hips and my ass. I had my own hands around one very cute girls' hips at one point as she ground herself heavily into my groin. She whispered in my ear asking if I wanted to get a drink with her, but just as I was about to say yes, I noticed Troy being kissed by another guy and he was very much into the kiss. For some reason I felt a surge of jealousy. I pretty much ignored the girl as I pushed my way through the dancers.

I touched Troy on the shoulder and when he turned towards me, I pulled him away from his dance partner and began to dance with him. Troy waggled his fingers at the other man and then turned his attention to me.

From that moment, we danced only with each other for the next fifteen minutes. His hands were on my hips, and mine touched his hips, his arms, I even caressed his face. Finally he leaned in and kissed me and I returned that kiss hungrily. We were lip locked for a full minute. He led me over to a table and we got fresh drinks. We held hands for a few minutes and then he suggested that it was time to leave.

He drove us home. We held hands in the car and I could not stop looking at him. At a stop light, we again kissed long and hard. I could not believe I was this hungry for a guy!

At the house, I invited Troy inside. Mom was definitely not home.

We made straight for the bedroom. And then we made out.

We practically tore each other's clothes off. Troy cooed when he saw my pretty panties. He was wearing a black satin gstring that bulged out obscenely, barely containing his hard cock. As I stripped that off of him, precum flew is several directions as his cock waved about.

He pushed me back on the bed and then lay his full length down upon me - by which I mean his body and his dick! He kissed me hungrily as his full cock length rubbed against mine. I thrust up against him. Rubbing cocks together felt so wonderful!!

We traded tongues hungrily for several minutes, pausing occasionally to look deep into each other's eyes. Fuck, I was so in lust with this guy! How could that happen!!

We rolled on our sides so that we could each grab hold of the other's dick. His fingers and fist felt so terrific as he toyed with my penis. I tried to follow suit, trying to fist him and give him pleasure, but really, I was just in lust with that beautiful cock.

Troy pushed me onto my back again. He made a few tentative licks as my nipples which made me squeal like a girl, but then his head reached my groin. He held my cock in his hand as he lapped at my balls. Then he stared straight into my eyes as he opened his mouth and quickly swallowed my cock right down to the root! It was amazing! How the fuck had he done that! I'm not huge by any means, but my dick is still long enough that it should have banged the back of his throat and stopped, but he had swallowed the whole thing in one go!

He withdrew and began licking my shaft. All the time he kept eye contact. Damn, he was so sexy when he did that!

He then bobbed his head up and down. I loved the look of his white blond hair with the deep black roots, especially as the hair splashed around as his head went up and down on my dick. As he sucked on me, he worked a hand underneath me and slowly inserted a finger into my ass! That felt so strange. At first he had just the tip in, then one knuckle and finally two! I squirmed on the bed, not sure if I liked this or not!

But I did love his mouth on my dick!

His finger continued to slide in and out of my ass as his tongue swirled around my dick head. He lifted his head and licked my dick head, again making eye contact with me. "I love your cock!" he said. And then he moved back up my body and we lay together again, lips locked tightly. He grasped both of our cocks in one hand and ground them together.

"God, I think I love you!" I cried.

"Nah, that's just your dick talking," he grinned at me. "Now, get down there and blow me! I want to see those sweet lips around my cock!"

I eagerly moved down the bed and engulfed his dick head. He was so fucking hard, and his cock was already so slippery from his leaking juices! I'd like to tell you that I sucked on his dick for an hour, but the truth is that I only bobbed my head up and down about three times before he grabbed my head, jammed his cock as far in as he could and then shot his jism into my mouth, yelling about how good a cocksucker I was. I swallowed his cum greedily. This was only my third load - two previous from Roger - and already I loved the stuff!

We cuddled a bit more and I pushed my still hard dick against Troy's thigh, but he got up and dressed. I looked at him plaintively, but he said that Mommy Jennifer's instructions had been that I was not to cum with him - this time.

"Be ready again at 9 pm on Friday night and I'll pick you up again!" He gave me a long hard kiss and then he was gone!

Frustrated, I wanted to wank off, but I decided first to check Mommy Jennifer's website. When I got the computer out from under the bed and then logged on, I found a flashing icon indicating that there was a video call waiting for me. I logged on and got a picture right away, but it was just an empty wall.

I went to the bathroom and looked at myself in the mirror. My makeup was a complete mess and my lipstick was gone. I took a couple of minutes to remove the makeup but I applied a new coat of the dark lipstick and straightened up my mussed hair. When I got back to the computer I had to wait another minute but then Mommy Jennifer appeared. She was a bit out of breath and her makeup was in disarray too. In addition she had a streak of cum across her left cheek.

I made a gesture as if to wipe something off of my own cheek. She grinned, wiped her cheek with her finger, looked at it for a moment and then sucked the cum off of her finger. God did she look sexy doing that!

"How was your evening with Troy sweetie" she asked. So I told her everything from start to finish and ended by telling her I was so horny because Troy had not let me cum!

"I wanted us to cum together tonight, Baby!" she said. She pushed her chair back and I saw that she had a raging hardon. "Do you like my cock, honey?"

"It's beautiful, Mommy!" I said. I pushed my own chair back so that I could see my own hard dick in the small picture in the upper corner.

We both began to jack our cocks and talk dirty to each other. "Did you like sucking Troy's cock, baby!"

"Oh yes, Mommy his cock tasted SO good! I loved swallowing his cum!"

"And did you like having his finger in your ass?"

"I... I don't know, Mommy! It felt so strange!"

"Girls like us love having our asses played with!" she cooed at me. Her big cock pulsed as she fisted it. I could see the pee hole opening and closing each time she stroked up and down!

Then she moved out of the picture briefly. When she was back, she scooched forward on the chair and lifted her legs so that I could see her asshole! It was open and drooling cum! Then she took a thick dildo and easily pushed the head inside. With only a bit of pressure she slid the length of the dildo fully into her ass until the fake balls at the end prevented it from going further.

"Oh god, that is SO wonderful!" she cried. "You are going to have to try this soon, sweetie!"

One hand continued to pump the fake cock in and out of her ass, while the other fisted her delicious dick! My Mommy looked so beautiful! I had not stopped fisting my own dick and I told her I was close to cumming!

"Me too baby! Me too! You look so fucking cute! I can't wait until we are together again! I want your lips on my cock sweetie!"

"I'm... I'm cumming Baby! Cum with me!" she said. She jammed the dildo into her ass and then arched her back. I watched as several ropes of cum geysered from her hard dick! I tightened my grip on my own dick and cried out as I spurted several spasms of sweet cummies high into the air!

We both took a couple of minutes to calm down, exchanging sweet words of love for each other. Then Mommy blew me a kiss and we signed off for the night.

I cleaned up again. I put on a clean pair of panties and crawled into bed. As I drifted off to sleep I kept seeing Mommy Jennifer pushing that hard dildo in and out of her ass and wondered if I would ever love doing that as much as she did!

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4 Comments
AnonymousAnonymousover 1 year ago

Great story and writing as always but please upload often

petey377petey377over 1 year ago

fantastic as always

petey377petey377over 1 year ago

i love this series (as i do all your stories) can't wait for more hope Mommy Jennifer will start training his boi pussy soon!!!!

LL180LL180over 1 year ago

Very well written again as usual,5 stars nice story,but there are so long gaps between each other.Waiting for the next story eagerly.

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Sweet Baby 04Ā Previous Part
Sweet BabyĀ Series Info

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