Surprise Packages

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

Belle was so anxious to fuck my ass that she then slathered up her own cock with lots of lubrication and proceeded to prod and probe my asshole while Tracy sucked me off. I was flattered that Belle wanted to fuck me so badly, but even she had to finally admit that I just wasn't ready yet, at least not for a cock as large as hers or Tracy's. Instead Belle and I decided to satisfy ourselves by double-teaming Tracy, with me fucking her mouth while Belle fucked her ass.

Afterwards as we all lay quietly on the bed, naked and entwined, I gave them my heartfelt thanks for everything they had given to me and everything they had taught me. I told them that I was sorry to be leaving tomorrow and I wished that I could move permanently to New Orleans because I felt at home and comfortable there. I also told them I would miss them very much but promised to return again as soon as possible. I truly meant every word.

Both Tracy and Belle were visibly sad and disappointed. They whispered together for a minute and then Tracy said, "Baby, do you think you can change your plans for just one more day? We had wanted to surprise you with something else tonight but it just couldn't work out. If you can stay just one more night, I think we can make it happen. I think it might just change your life. Please!"

I had grown to trust Tracy's sense of perception and the thought of another night of ecstasy with these two beautiful girls and their impressive cocks was too much to turn down. They left me that night happy with my promise that I would rearrange my travel plans for one more night. I immediately called down to the front desk and was lucky to find that I could even stay in the same room.

The next day I was back to being excited and anxious again. Tracy's words had sounded so powerful to me and I spent the hours waiting and wondering what would happen. I didn't have to wait quite so long this time because I heard the familiar tap on my door at 9:00 p.m., a full hour earlier than usual. Luckily, I was ready; hell, I had been ready for almost three hours in anticipation.

I opened the door with bated breath and in walked Tracy and then Belle wearing long overcoats. I started to shut the door but stopped when I felt a push back. In followed another girl and she gave me the cutest smile as she passed me by and said, "Hi Tom! It's nice to meet you. I've heard so much about you."

The girl was petite standing there in her long overcoat. The other girls introduced her as Cindy and I could see how different she was. She was much smaller in build than Belle or even Tracy. She was also black but her skin was very light brown in tone. Her hair was long and straight, dyed a bright blond but with bright streaks of green, pink and blue and it was divided and tied into two long pigtails on either side of her head. Her full, pouty lips were highlighted with bright pink and sparkly lip gloss. What amazed me the most was how young she appeared.

All the girls were beaming at me with big smiles and then Tracy spoke, "Sorry about the coats but we felt weird walking through the hotel dressed like this." With that they all removed their coats revealing that they were all wearing matching cheerleader outfits with short skirts and bare midriffs. They even had little sneakers with short ankle socks. They had really dressed for the part.

I laughed and told them how beautiful they all looked, but I noted how this outfit only enhanced Cindy's very youthful appearance and I was a little concerned. I quickly pulled Tracy and Belle to the side and asked how old Cindy was because she really seemed like she could possibly still be in high school. Tracy whispered to me, "You don't have to worry a bit, sweetie. Cindy is definitely of legal age." I relaxed a little as Tracy and Belle turned back. I'm not certain, but I could almost swear I heard Tracy whisper out of the side of her mouth toward Belle saying, "Just barely!"

I stood there showing my nervousness, which was contradicted by my stiff erection straining at my pants. Tracy looked at me and said, with just a trace of disappointment in her voice, "If you're still worried about it, Cindy doesn't have to join in tonight, but you at least have to let her perform with us to show you the special cheer we made up just for you!" I agreed and they told me to sit on the floor while the girls lined up.

The cheer was very cute and funny and a bit haphazard. It was also very dirty and mentioned in a very funny way my newfound skill at sucking their cocks and getting fucked in the ass. By the end of it we were all laughing and having fun. It was so good that I asked them to do it again and this time they did an even better job, more coordinated and with more movement.

About midway through this second cheer Cindy performed a different move than the other girls. While facing away from me and spreading her legs very wide she proceeded to bend way over enough to look and smile back at me from between her legs. That's when I saw that Cindy had nothing else on below her short skirt. Her ass was clearly visible, and below that hung her very cute little balls and penis. I quickly looked over toward Tracy and Belle and they were doing some jumps, also revealing that they had no panties on either. Their long cocks were bouncing and swinging around freely with each movement. I was shocked but my erection felt like it was going to split my pants wide open.

The girls did their big finish again, but this time with one last big jump toward me. They all landed right in front of me, no more than a foot away, with their legs apart and their skirts pulled up high. All three girls were breathlessly smiling down at me while their cocks were fully exposed at my eye level and pointing right at me.

Right there in the center, closest and directly in front of my face, was little Cindy; her cute cock and balls were beckoning me to come closer. I could see that she was much smaller in size than Tracy or Belle. I think she was even smaller than me although she wasn't fully erect at the moment. I just knew that my fears and uncertainty were instantly gone and replaced by pure desire. I couldn't wait any longer to taste this new treat the other girls had brought for me!

I immediately moved to my knees and straight for Cindy as she welcomed me in. With an open mouth I dove onto Cindy's cock without a word and enveloped it fully while simultaneously reaching out with both hands for Belle and Tracy's cocks to either side. Cindy's penis was still only half erect and using my tongue and lips I sucked and squeezed it in my mouth and immediately felt it growing larger inside me. It felt so amazing and tasted so sweet! Very soon it was fully rigid and I released it from my mouth and sat back to admire her.

Her pretty face was still smiling down at me and I couldn't help but notice her beauty. My eyes moved downward and her body looked fit and trim beneath the cheerleader outfit, with small but perky looking breasts. I was hoping to see her fully naked body very soon, but for now my eyes moved back down to where she was still holding her skirt up for me.

Although Cindy's cock was still smaller than mine, it had similarities to Tracy's impressive cock because it was perfectly proportioned, fairly thick for its short length with a well-defined head, and it was very straight. It was just too much for me to stand and once more I hungrily devoured it, but this time I brought both of my hands around to grab Cindy's sweet little bare ass and pull her body tightly against my face. I heard Tracy say to Belle, "See? I told you he would like her!"

I tried to go slow and savor the taste and feel of Cindy's cock in my mouth, but the longer I did the more I wanted to bring her to an intense climax, to bring about for her strong pangs of pleasure, and for me to taste her sweet cum. I guess it was my inexperience that caused me to rush forward like this but I couldn't help myself. I was soon fiercely deepthroating Cindy's cock, plunging it deeply in and out of my mouth, and she was now gasping her breaths in response to the fast-paced intensity with which I was mouth-fucking her.

I could hear Cindy moaning in pleasure at my still-inexperienced but very focused attention on her stiff cock and that spurred me on even more. I'm sure Cindy was surprised by my single-minded focus on sucking her cock. She had just met me and we had barely even spoken and here I was performing one of the most intimate acts possible between two people. I was even surprised at myself, but I just couldn't stop.

I took only very short breaks from sucking her cock in order to catch my breath, and when I did, I would give some attention to Cindy's very cute and clean-shaven balls that were also tight and smaller than the other girls. They were such a pleasure to take into my mouth and lick and suck, but I kept returning to that pretty little cock of hers.

Tracy and Belle, appropriate to their outfits, were now cheering me loudly on, amazed themselves at how strongly I had first reacted and thrown myself onto Cindy with such ferocity. I kneaded her tight little ass and pulled her closer as I deeply thrust her cock again and again into my mouth and sucked on it almost as if I was dependent on it to provide my life-breath.

I'm not sure why I reacted so strongly to Cindy; I just did. I had been so impressed by the beauty of Tracy and Belle when I first met them, and I had been awed by the size of their impressive cocks. But with Cindy there was just something about her petite figure with her clean, smooth skin and perfect little cock and balls that aroused me so much. I couldn't resist her and I was intent on bringing her to a quick and intense orgasm, and even with my rookie cock sucking skills I was apparently succeeding.

Cindy now grasped my head with her delicate hands, her fingernails painted in dayglow green, pink and blue to match the highlights in her pigtails. Cindy was now panting and crying out loudly and I loved hearing the sounds of her squeals above the raucous cheers of Tracy and Belle. Cindy was now pulling on my head while at the same time grinding her slender hips and pelvis hard into my face, and I could feel the tip of her cock moving even deeper and tickling the back of my throat.

That was the moment when Cindy gave out her loudest cry yet. Once more she pulled my head strongly in against her body and I braced for the inevitable. I felt her balls constrict against my chin at the same time that her cock swelled against my tongue and then I felt a flood of warm liquid washing the back of my mouth.

I felt the same swelling of her cock several more times as spasm after spasm racked Cindy's petite frame and sent the warm ejaculations of Cindy's cum into my mouth. Although she was petite in stature, she produced a surprisingly large volume of cum that was quickly filling my mouth, but I was happy and eager to take it all in. It made the bond between us stronger, at least in my own mind.

When she was finished, I was struggling to contain it all, and then I struggled even more to swallow it all down as I sucked out the last remaining drops before releasing her from my mouth. I fell back on the floor and Cindy dropped on the bed, both of us completely spent, while Tracy and Belle continued to cheer for us loudly.

It took us both a little while to recover and once I did, I had my first actual conversation with Cindy. She was delightful, funny and charming. We all laid on the bed and talked and laughed. I was so happy that the other girls had brought her along. I learned that Tracy had the idea of bringing Cindy along the night before because she thought that with her smaller penis, I might be able to experience what it is like to be fucked in the ass. Tracy really wanted my experience with a T-girl to be complete.

Well, guess what? Tracy wasn't wrong! Soon the four of us resumed our sexual fun and I had a chance to experience and enjoy everything, and I do mean everything! Without going into too much detail I will tell you that I experienced each one of these beautiful women's cocks multiple times that night and had my fill of their cum. At one point I was surrounded by three she-cocks at once and I became dizzy going around and around from one to the other.

Somewhere in the middle of that night Tracy got her wish, and with the help of much lubrication Cindy successfully fucked me in the ass to the loud cheers of Tracy and Belle. It took some getting used to at first, but by the end I was hooked. It helped that both Belle and Tracy serviced my cock while Cindy fucked me in the ass. I must admit that my orgasm from that was very intense, and it barely proceeded Cindy's own climax inside of my ass. Another first for me!

I was also lucky enough to get the chance to fuck each one of the girls in turn. In fact, I think the second favorite thing for me from that night was first tasting, and then fucking Cindy's sweet little asshole! She has a picture-perfect ass and I rejoiced at burying my face between those sweet little cheeks. And when we fucked, she felt so good on my cock. We just felt so right together. Of course, my most favorite thing of the night will always be that first, fast and furious, and clumsy cock sucking that I gave to Cindy. It was our first, but not our last.

The four of us spent all of that night enjoying each other fully. We had so much fun and made so much noise that the hotel management called three times to complain and it wasn't until they threatened to call the cops and have me thrown out that we settled down into a quieter activity. Suffice it to say that the solution we arrived at was to form a circle on the bed so that we each had someone else's cock in our mouths at the same time. That did a very good job at muffling most of our sounds. I'm sure you get the picture!

The girls never left my room all night and we all tumbled together in the bed and slept till noon, which was when the maid knocked and told me that I was supposed to have checked out already. I also realized that I had missed my plane, but I didn't give a shit.

In retrospect, I owe my ex-wife a huge debt of gratitude. If we hadn't had such a shitty marriage and my slut of a wife hadn't cheated on me, I would have missed all of this! And I certainly owe much thanks to Tracy and Belle for introducing me to the pleasures of T-girl sex. Who knew I would love sucking cock so much?

But I owe the most to Cindy, for you see, she changed my life for good. After that first night I called my work and told them I needed at least a month's leave of absence to deal with a personal crisis. They grudgingly agreed and that allowed me to stay on in New Orleans. Then I pestered Cindy every day until she agreed to see me, not as a client but as a man.

Actually, it didn't take too much to convince her because even she quickly realized that we had something special together. It wasn't long after that that we started to spend every day together and we have never parted since. Simply put, I had fallen in love with Cindy that very first night.

I eventually called to quit my job and I sold my house and moved my entire life down to New Orleans to be with Cindy permanently. She and I now live together and we couldn't be happier. We are still very close with Tracy and Belle and every so often, just for fun, we all recreate that memorable night with the cheerleader costumes. At least now we can be as noisy as we want. Who could ask for a better life?

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
5 Comments
Client8Client8about 2 years ago

This was pretty good. But, it went right into the action on page 1, not leaving a whole lot of mystery for the final 3 pages. Plus, it was a bit too focused on oral. When the first person character did finally get his maiden ass fuck, it was really rushed through and did not describe much of the feeling of the act. Otherwise not bad. Could've been shorter as an initial chapter of several, or more complete in just this story. I liked it anyway.

GrrrreatImaginationGrrrreatImaginationover 2 years ago

Such a great story. The personal development was heartwarming, the sex was sizzling. I have to say though, "Without going into too much detail" is an indicator that the story should be broken into another chapter. I imagine reading about him losing his anal cherry with the detail you gifted us with describing his initial cock-sucking. Mmmm.

RhondaParker54RhondaParker54over 5 years ago
Awesome

Well, it certainly was a surprise package, very engaging from the start. I don't think I would have wanted to leave New Orleans either. Waiting for your next submission.

SparkyMark1961SparkyMark1961over 5 years ago

Can I just say, THAT WAS FREAKING AWESOME!!!!

Loved it and I am glad that you were able to stay with Cindy.

I was hoping for that.

Bama71Bama71over 5 years ago
Surprise indeed

Well-done. Would love to read more stories like this from you.👍

Share this Story

Similar Stories

My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
My New GF has a Dick And I love every last inch of it.in Transgender & Crossdressers
Southern Hospitality Milfy seductress does all she can to score the boy next door.in Transgender & Crossdressers
More Stories