Panty Boy Ch. 08

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Further adventures of Stacy and Megan.
4.9k words
4.71
129.9k
26

Part 8 of the 9 part series

Updated 11/02/2022
Created 08/22/2006
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I had to go out of town for a meeting; my ass was very sore from the night before. Those girls had really given it to me; my asshole was left a gaping hole. I could feel the "lips" of my asshole for over an hour last night, all big and puffy and open waiting for more. I felt like a total whore and I loved it. I took three huge cocks and was left begging for more.

I had to catch a flight in a few hours. I had a business meeting the next day and a long flight ahead of me. I slipped out of the bed as not to disturb Megan. I got up and showered. I wasn't looking forward to the flight, but I didn't have much of a choice.

I made myself breakfast and went to the dining room where I saw the box of toys. I thought to myself how much I wanted to bring all of them with me. I was going to be gone for a week and knew that I would get lonely, my mind replaying all the events of the night before. My ass was now used to having something in it and I loved the way that it felt to be full.

I went upstairs again to pack my bag and get dressed. I put a pair of pantyhose on and just thought about "sneaking" a toy on board with me. I slipped a medium sized plug into my ass and moaned with excitement. As I prepared to leave, Megan came down with an extra bag.

"You almost forgot something!" She said, giving me a wink and a kiss on the cheek.

"What is this?" I asked.

"Just a little something to remind you of your place. Just promise you won't peek until you get to your hotel. You were such a good little slut last night"

"I promise." I said as my mind danced at the thought of what she might have in mind. I grabbed the bag from her, kissed her, and left for the airport.

Traffic was really bad and when I finally arrived at the airport I was running a little late. I checked in and ran to the gate hoping that my plane was still there. I got on right before they closed the doors and settled into my seat, the plug pressing in deep into my ass. My mind wondered what was in he bag as I settled in and fell asleep with a little grin on my face.

The flight was long; I awoke about halfway through and all I could think about was the night before and how Megan and her friends were using me and how much I absolutely loved it. How I was begging them for it. My cock was hard pressing against my hose. I rubbed my legs together sending a wave of excitement up my body. Every time I moved I could feel the plug moving deeper inside me and it felt so good. At one point, I thought about going into the bathroom and relieving myself but then thought how much better it would be to be able to enjoy it when I got to the hotel and could see what Megan had sent with me. I was really excited.

When we landed, I got off the plane and hurried to the rental car desk to retrieve my rental car so that I could get to the hotel as fast as I could. I was excited to see what Megan had packed for me. I had all night to have some fun by myself.

The whole ride to the hotel I was hot with anticipation. I arrived about a half an hour later, and checked in. I got to my room, set my bags down and immediately opened the bag that Megan had packed for me.

Inside I found a whole wardrobe of my new favorite clothes and heels. Megan had packed me enough for the whole week and my cock grew just at the site of them. In the bottom of the bag was the strap on that Michelle was wearing the night before and a couple of the larger plugs, my breast forms, and some make-up. The cock still had my dried cum on it. I found a box that was wrapped and a little note attached to it.

"To My Sissy Slut, Stacy" the envelope read. I opened it quickly:

"It was so hot to see you and the girls go at it last night baby. I didn't want you to forget your place so I packed you a few things. You really seemed to enjoy that huge cock last night so here it is. I hope your ass is ok. You just couldn't seem to get enough of that big hard cock. I also got you a little something so that I can keep an eye on you to make sure you aren't having too much fun while you are away from me. See you soon. Enjoy!

PS. You should try to go out while you are there. Have some fun, but not too much or I will have to punish you when you get home"

I opened the box and found a web cam. I was so excited. I hurriedly changed in to my other clothes put on some make up, and hooked up the camera to my computer. I removed the plug that I had worn all morning and slipped in a larger plug. I just loved the feeling of being opened wider and wider. I also slid into the ultra high heels Megan had sent with me.

I started to think and got a little embarrassed when I thought about that bag going through the x-ray at the airport. All the security must have seen the heels and the cock shaped toys in my bag. I laughed a little bit as I logged onto my computer. Megan immediately messaged me.

"Hey Stacy, I am glad to see you got your gift. It was so hot seeing you beg for that cock last night. I can' believe how you were begging for it last night. My little slut really loves her cock now, doesn't she? I knew she would. I hope that one day soon we can share a nice big real cock." Stacy said

"You know you want to, the way you were begging for it. I am so glad you like cock as much as I do. I think we are going to have a really good time from now on. Let me see your cock Stacy. Are you stroking it right now?"

"Yes" I said pulling on my hard cock. I was so turned on right now and I couldn't help it.

"Would you suck a cock with me, Stacy? I think it would be so hot. Watching those sissy lips wrapping around a long warm cock, watching it fill your mouth. Let me see your hard clit. Do you have something buried deep in your ass? " Megan said as she stood up revealing that she was only wearing her strap on. She was stroking the tip of it.

"MMMM this cock is so hard. I can see how badly you want it. You want to feel it sliding all the way into your tight pussy don't you Stacy, taking it deep into your tight ass pussy. Feeling every inch. Beg me for it."

"I want you to fuck me, Megan." I said stoking my cock harder rocking back and forth on the plug buried deep in my ass. "I want you to fill my tight little hole. I want to suck your hard cock."

"MMMM... I knew it. You are such a little sissy slut. Show me your tight filled ass Stacy. Show me your open pussy!" Megan said.

I stood up and bent over for the camera spreading my ass cheeks apart so that she could see my plug filled ass.

"MMMM, look at that open hole. I wish I could fill you up right now. I want you to go out to a club tonight and flirt for me. We have to get you used to going out. You have absolutely nothing to lose baby. Nobody knows you there. I packed you those things so that you could get dressed up and go out and enjoy your new life as a woman. I am just sad that I cannot be there with you. You better be good." Megan said.

It was so hot watching Megan, the way that she stroked the strap on using it like it was in fact a real cock. I loved the way she was teasing me with it and all I wanted was to be on the receiving end of it.

"I am going to run and get dinner, Stacy. I am going to wear this cock out. Why don't you get dressed in your sexy clothes and go out and grab a bite as well? We can meet up a little bit later and see what is going on. Keep your little clitty in control tonight and be a good girl." She said blowing me a kiss and logging off of her computer.

I couldn't believe how turned on I was. I just continued stroking my cock. I walked over to the bag and pulled out the strap on. I was sitting there in stockings, heels, and panties in front of my computer stroking my cock with a big plug in my ass and a long, thick dildo in my hand. I started to rock back and forth, the plug pressing against my prostate sending a wave through my body. I soon found myself sucking on the dildo wishing that Megan and one of her friends could be attached to it.

The biggest thrill was thinking about how big of a slut I had become. I loved the feeling and was imagining about what Megan had said about sharing a cock with her.

I have to admit that the thought did excite me a little bit. Not knowing what it would be like to feel the warmth of another man's cock in my mouth, feeling the hot come explode in my mouth. I closed my eyes pretending that the strap on was the real thing. I wanted it bad. I sucked harder, continuing to stroke myself. I was so close to coming, but then I thought that I would like to save it for tonight. I did not know what would happen but decided that I would love to go out in this little town I knew no one in and see what could happen.

I released my cock and walked into the bathroom to get cleaned up and ready to go out. I quickly hopped into the shower and shaved my legs. I made sure to get every last bit of stubble off of them before shaving my face. Lucky for me I have never had thick beard growth. I got out of the shower and quickly toweled off before putting lotion all over my body. I loved the feeling of pulling the pantyhose over my freshly shaven, freshly lotioned legs. I sat down on the bed to put on the pair of heels.

Once I got the straps on the heels fastened, my fingers took a detour and I found myself lying on the bed finger fucking my asshole. I was dying to have something big filling me up tonight. I reached over to the nightstand and grabbed the strap on.

I needed to be filled so bad right now, so I pulled the pantyhose down just enough, and attached the strap on to the seat of the chair, and straddled the cock, slowly pressing it into my accepting hole. I turned on the Web cam and hit record so I could see myself in action.

My asshole was a little worn out from the night before, it was still a little bit swollen from all the attention it got, but I had to have something big inside me. I craved to have the thick cock buried in my ass again so I put more lube on it and continued to slowly stretch my pussy over the cock. Once the head popped in, it only took a little bit of time, before I was sliding down the whole ten inches. It helped that I had worn the plug for a few hours today. I loved the way it felt and I continued fucking myself harder and harder with the strap on, watching myself on camera. I was in complete ecstasy. I loved watching myself in action. I cannot help but to be turned on by it. I bucked harder and harder, sliding up and down the large shaft, my cock bouncing with the rhythm. I wasn't even stroking my cock and I could tell that I was going to come soon. I had been on the verge all day and felt as if I needed a release.

As I approached the point of no return, I grabbed my cock and started stroking. My cock grew, the strap on sliding effortlessly in and out of my gaping hole. I moved the camera to get a better view of the cock sliding in and out of me.

Every time the cock would pop out I was left me with a huge gaping hole. I loved the way it looked to be so open. To have my hole well fucked. I moved the camera in closer. I was wide open; the cock would then slide back in to me with no resistance.

I placed the camera back on the desk and just watched myself on the screen, fucking the strap on long and hard. I was really close to coming now, I buried the cock deep in my ass, feeling the balls of the dildo pressing on my ass cheeks, I imagined it being the real thing, my come erupted from my cock, exploding all over myself, spraying my warm gooey liquid all over. It shot in streams into the air. Being the good slut that I was, I didn't want to waste anything so I made sure to get every last drop and clean it up. I even saved a little bit for the plug that was waiting for my ass for when I went out tonight.

I lifted up off of the dildo, it slid out of my loose ass, and I picked up the biggest plug that Megan had sent with me. I rubbed the plug it with the come that was on my hands and in my mouth and then slid it into my ass filling the void from the strap-on with hot sticky cum, licking my fingers once it was in place.

I was such a cum greedy slut. I couldn't help but want things in my ass. I was ready to go out. I was on the prowl. I pulled my pantyhose up my legs and slid my red leather mini skirt up my nicely shaven legs. I was almost ready to go out. I touched up my make-up, put on my sexiest bra, and slid the breast forms into place. I pulled a sexy silk blouse over my bra and looked in the mirror.

I looked hot. I got a little bit closer to the mirror to apply my lipstick. I looked sexy without looking too much of a slut. I looked as if I got off of work and was just a girl in need of a real good fuck. I was going to go out and see what would happen; tonight I was open for anything. I grabbed my purse and put a couple of extra things in it and headed out the door. I felt sexy and was still really horny.

When I got into my car I really couldn't believe what I was doing. I hesitated for a moment. Here I was in a town that I had a business meeting the next day and I was dressed in women's clothing and was going out looking for a fuck. Although I don't quite know how this all came to pass, I was so excited by the though of it. I wanted it bad... in fact I needed it.

I drove around for a while until I pulled into a place that looked promising. It was close to some office buildings so I thought that I might fit in. I took one good look in the rear view mirror and adjusted myself one last time before letting myself out.

I stepped out of the car, the breeze cool on my freshly shaven pantyhosed legs. It took me a minute to get adjusted to the high heels I was wearing and the huge plug in my ass, but it didn't take me long to perfect my walk. In fact I think the plug helped my walk.

I walked into the bar and took a look around. It wasn't busy a few people here and there but I noticed that I had made my mark. I could feel the eyes of the room on me as I walked across to the bar. I was a little nervous, this being my first time out alone as Stacy.

I walked up to the bar and took a seat. I ordered a drink and just sat and watched the people at the bar. The bar wasn't exactly what I thought it was when I pulled in, yeah there were a few business type guys but mostly there were more of a younger crowd. The town was small and I guess there wasn't much to do.

I few people came and went with nothing really to say when all of the sudden someone came up and sat down next to me. He was a good-looking man in his late 20s and he immediately started talking to me. I was quite nervous but tried to play as cool as I could.

"I've never seen you here before" he started, "My name is Mark."

"Hello, Mark I am Stacy." I responded

"Where are you from Stacy?" He asked

"I am from New York, just here on business."

"How long are you in town for?" Mark asked.

"About a week." I responded.

After a few minutes, I got up and excused myself to go to the bathroom. I was really nervous about this meeting and had to go calm down.

This was the first time that I had ever been faced with the problem of going to the bathroom as Stacy and almost walked right into the Men's room. Luckily I caught myself before. I walked in to the ladies room and went into the stall. I was shaking. I was so nervous that I would be found out. This was my first time out alone as Stacy and all I could think of was what have I gotten myself into and what am I doing here. I squatted and pushed my cock back to make a more woman like sound from the pee hitting the toilet. I finished up and even wiped my little clitty off. I readjusted my plug and pulled up my pantyhose. Although being nervous, I felt really sexy and went to the mirror to re apply my lipstick.

Looking into the mirror I regained my confidence. I looked good, I mean I looked fucking hot, and walked out of the bathroom now more self-assured what I was doing.

As I walked down the hall from the bathroom I noticed a stairwell that went down into the basement and could hear music pumping out of the doorway. It seemed as if there was a dance club underneath the bar I was in. I love to dance and knew this was where I would find what I needed.

I walked back to find that Mark had bought me another drink. I sat down next to him and talked to him some more. We sat for a while and talked.

After an hour or so, I was really horny and after a few more drinks I really wanted to dance. I grabbed Mark's hand and pulled him up off of his chair,

"Do you dance?' I asked him, "Lets go down and dance, I love to dance"

I wasn't sure if Mark really enjoyed dancing but he was a great sport about it and I was not about to let him have a bad time. The music was pumping and I don't know if it was the alcohol but I was all over him. He held my body tight against him and I could feel his hardness bulging into me. I wanted to feel him when he pressed his cock against my ass and whispered into my ear.

"I know your secret." He said, moving his hands down to my crotch giving a light squeeze

I was mortified. I didn't know how to react but I tried to stay calm. I pressed my ass back against him.

"What are you talking about Mark?" I responded.

"Don't worry, its ok." He said pulling me off the dance floor into a dark corner.

His mouth touched mine and we were in a full embrace his hands all over my body, kissing me. His lips were soft and wild thoughts were passing through my mind. I couldn't believe what was happening to me but I loved it. My little clitty was so hard. He turned me around and hiked up my skirt. I soon felt his cock against my pantyhosed ass.

"I want you now." Mark whispered into my ear.

"Lets get out of here" I said kissing his neck.

We walked quickly up the stairs and out of the bar into the parking lot. When he grabbed me and pushed me up against the door of his car. He was all over me. My head was so clouded and it just seemed right we continued to kiss.

"Please follow me to my hotel." I said

"Why don't you just ride with me?" He asked.

I knew that I had to be at work the next day and told him that I couldn't. We got into our cars and I sped back to the hotel as fast as I could.

The whole time in the car my mind was racing. I couldn't believe what was going on. I was excited and scared but I couldn't stop myself. It seemed to take forever to get to the hotel but we finally arrived. I stumbled with the keys at the door but as soon as I got the door opened he was all over me.

I managed to get out of his embrace and went down on my knees. I unzipped his pants and his cock sprung fourth. It was beautiful and big and uncut. I took it in my hands and just felt it. It was so different from holding my own cock .My long red nails stroking the big beautiful cock in front of me. Mark let out a moan. I then brought my bright red lips to the tip and kissed it. It was nice and warm. It wasn't long until I was sucking it like I had sucked Megan's strap on but the real thing was so much better. I could not stop sucking on it. Mark just grasped my head and looked down at me.

"Oh my god Stacy, you are such a good cocksucker. Show me how you like to suck cock." He moaned.

I just continued. I could taste his pre-cum in my mouth. This was the first time I had ever tasted another mans come and I loved the idea of it. I wanted to feel him shoot in my mouth. I wanted to feel his sticky warm load shoot into the back of my throat. I sucked with a little more effort.

"Oh baby, you suck so well but MMMMMM..." He moaned.

I managed to get my mouth of his cock long enough to say, "But what Mark, What do you want? Let me be your slut tonight. Use me however you seem fit."

I felt his balls tense up. I could tell he was close to coming, when he pulled me back to my feet. My heels made me just a little bit taller than him. He turned me around and pushed me against the wall.

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