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An Introduction To Crossdressing, The Finale

"As Jackie, Chandra and I finished up our food, we chatted about the evening yet to come."

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Reliving our evening’s events had Jackie and Chandra pretty worked up.

“You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?”

Simultaneously they both grunted, “Yes we are!”

I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy.

“You should probably save some of that for back at the hotel, before you run dry,” I said.

But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done for the evening, are you little horn dogs ready to go?”she asked.

Immediately, Jackie and Chandra let each other’s joy sticks go. They jumped to their feet and headed for the door.

Susan and I just stood there for a moment, slack-jawed until she finally said, “I guess you will be needing a ride then.” We both broke down laughing hysterically and headed out the door.

As I walked with Susan to her car, Jackie and Chandra pulled up and asked me, “Do you need a ride to the Hotel, or are you going with Susan?”

I told them, “I’ll ride with Susan and we’ll see you there shortly.” As they drove off I turned to Susan and asked, “Is your husband meeting us there or are we going to pick him up?”

Susan replied, “If it’s alright with you we can go pick up Bob and still be at the hotel in twenty minutes.”

I said, “That’s fine with me, it will give us some time to chat about what you would like to do with us in bed.”

As we continued walking to Susan’s car, she slid her right hand under the back of my skirt and started fondling my ass. She continued her assault by sliding her middle finger in and out of my ass as we walked. When we got to her car my cock was showing signs of life from all the attention to my ass. Apparently that was her plan.

When we got to the car Susan accidentally dropped her keys and bent over at the waist to pick them up. As her skirt climbed up the back of her thighs, it was quite apparent that she was not wearing any panties, and she'd done it on purpose.

Being the smartass that I am, I asked, “Susan do you need some help finding your keys, and your panties? They seem to have fallen off somewhere, leaving your pretty little pussy exposed for anyone to see.”

Susan glanced back and me and said, “I’d love it if you would stick that hard cock of yours into my pretty little pussy and fuck me.”

Without another word, I stepped forward and slid all the way into her hot, soaking wet pussy. We both moaned aloud when I hit her bottom and it felt so good that neither of us moved for a few seconds. As I slowly started moving in and out of Susan, she started getting very vocal. That’s when I was reminded that we were in a parking lot.

Now I’m all for being an exhibitionist, but when a woman's moaning loudly in earshot of others, and it could be misconstrued as something else, I start to get a little nervous. Especially with me being dressed the way I was and others still exiting the club. But there was obviously something I didn’t know because the only attention we got were some cat calls and whistles.

Susan noticed my apprehension and said, “Don’t worry about anyone; they all know that I’m loud and love to get fucked in the parking lot. It just really gets me hot!”

After hearing that I started pounding her in earnest. It wasn’t long before she was cumming all over my cock and balls. I slowed to a stop, leaving my still hard cock deep within her while I waited for her to recover. As Susan stood, she slid off of my cock and turned to give me a very deep wet kiss.

Upon breaking the kiss a minute later, she said, “Thank you so much, I really needed that after watching your girls play with each other all night.”

As we got in the car Susan said, "I know you didn’t cum but I think you’ll really enjoy the ride from my house to the hotel.” She then called her husband Bob and told him, “I have a treat for you honey, gather our toys and meet me out front in ten minutes.”

After hanging up the phone, she told me, “I know I told you that my husband and I like girls like you but Bob really loves your kind. He really enjoys sucking girly cocks, even more so if they have been in my pussy and he loves to lick your ass-pussy’s. So pull off those panties, get in the back seat and spread those legs because Bob’s tongue is magical.”

By the time Susan was done talking, I was so hard that I was afraid to touch myself for fear that I would cum. So I gently removed my soaked panties and stuffed them in Susan’s purse. As we pulled into her driveway, I climbed into the back seat as she had instructed, and waited for Bob. When we came to a stop, Bob came out of the house carrying an overnight bag

Susan said, “Bob, this is Denise and she just fucked me in the parking lot at work but didn’t cum yet. Do you think you could help her out with that?”

Bob handed Susan the bag, opened that back door and got in. I was spread eagle with my left leg on the top of the back seat and my right on the top of the passenger seat. Bob was an attractive man about sixty years old, in good shape, and about my size. He was also very much the gentleman.

“May I enjoy your goodies?” he asked me.

I replied, “Please do”

And with that, he proceeded to lean down and run his tongue the length of my cock, causing it to twitch uncontrollably. Sensing that I was very close to cumming, he grabbed both of my ass cheeks and spread them wide. Bob started licking all around my hole, never quite touching it and occasionally sucking on my balls. When he finally licked across it, I thought I might cum just from that alone.

Again, he must have sensed that I was close, so he just blew gently on my ass until the feeling started to pass. When Bob was sure I had calmed down he started licking circles around my hole. Soon he was moving his tongue up and down and side to side across my sensitive ass. I noticed that he started increasing the pressure with his tongue and, before long, he was moving in and out of me.

As I started to moan like the whore I am, Susan said, “You are about to learn why I love Bob so much.”

As soon as Susan said this, Bob started tongue fucking me in earnest. He went so deep, it felt like a cock.

I started screaming, “Fuck me Bob, fuck me hard!” over and over.

This is when Susan piped in again saying, “Bob’s tongue can extended about three to four inches out of his mouth. It’s like having a flexible cock with a directional tip.”

It was only another minute before I was screaming, “I’m cumming, O God I’m cumming!”

I didn’t have much cum left, but Bob got what little there was by pulling out of my ass and engulfing my cock as soon as he could. The orgasm was so powerful, I passed out for a minute or two. I awoke to Bob licking me clean from stem to stern.

As I gathered my wits, I realized that we were in the Hotel parking lot and Susan had already gone inside. So I reached down and pulled Bob up on top of me and gave him a long sloppy kiss.

When we parted I said, “Why don’t we go inside and have some more fun.”

To which Bob replied, “I can’t wait to get naked and fuck that sweet ass of yours.”

Of course this caused me to pull him in for another long sloppy kiss and I even wrapped my legs around his lower back and ground my cock against him. As the kiss wound down Bob started to pull away.

“If we don’t get out of here right now I’m going to fuck you in the car,” he said.

With my legs still spread, I started fingering my ass teasingly.“How close are you? I think it would be so sexy to have your cum running down my leg when we walk into the hotel room.”

And with that statement barely out of my mouth, Bob pulled down his pants and slid his average sized penis right into my ass. He didn’t last more than about two minutes but he did hammer away most of the time and it felt fantastic to be fucked hard.

Bob grunted loudly as he came, filling me with several spurts of his seed. It felt great every time he shot another load. We were kissing gently as he came down from his orgasm, still deep inside of me. When we finally parted, I made a point of squeezing my ass tightly to keep the cum inside until I was upright and walking.

Bob helped me out of the car like a proper gentleman and, after I got myself organized, we walked arm in arm to the Hotel room. As we made our way to the room via the lobby I could feel his cum running down the inside of my thigh and made no attempt to conceal it.

We got on the elevator with another couple. Immediately, the woman noticed my leak and gave me a knowing smile. She leaned into her date’s ear and whispered something. He looked at me with a very sly grin and gave a quick squeeze of his own cock. Then he whispered something into her ear which caused her to blush a little.

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As the elevator doors opened to our floor she asked me if we were interested in a coming down to their room for a drink.

Bob and I looked at each other, stepped out of the elevator, then I turned to them and said, “We would really love to but we have other plans tonight and I’m not really what you think I am.” I raised my skirt showing them my cock and, as the elevator doors closed, I watched their expressions run from mild disgust to curiosity and desire.

The scene in our room was what you might expect, knowing the characters involved. Chandra was lying on his back with his legs pulled back and spread wide. Susan’s face is in his crotch sucking on his balls and licking his cock. Susan didn’t have a stitch of clothing on, with her ass high in the air at the edge of the bed. Jackie was busy fucking her pretty little pussy at a nice slow pace, causing a moan to escape her lips every few seconds.

They were all so into the pleasures that they were giving and receiving, they didn’t even notice us for about five minutes. In that time, Bob had removed all of his clothing and was slowly stroking his own cock to the rhythm of Jackie fucking his wife. When they finally noticed we were there, they all moaned a collective hello, never stopping what they were doing.

I moved to Jackie and whispered in his ear, “Bob is the best ass rimmer ever, and he has a four inch tongue which will drive you insane. He also loves to suck cocks after they have been in his wife’s pussy.”

Jackie whispered back, “What do I have to do to get some of that action?”

I replied, “Go lie on the bed next to Chandra and spread your legs. I’ll fill in for you with Susan.”

As Jackie pulled out of Susan and spread out on the bed, I slid right into her barely missing a stroke. Susan’s pussy felt heavenly and it seemed that she was getting close to one of her screaming orgasms based on the noises coming from around Chandra’s cock.

Just about then Susan’s head popped up and she said, “Harder and faster I’m almost there.”

So I picked up the pace and really started slapping into her hard as she went back to sucking Chandra. While I was working to please Susan, I turned to see Bob’s tongue working on Jackie’s appreciative ass. I know how Jackie felt as I was recently on the receiving end of that tongue. Feeling it was one thing but to see it slide in and out like a small cock was amazingly hot.

Slowly the volume of moans and grunts started increasing and, within a couple of minutes, it sounded like a herd of buffalo were coming. It seemed as though everyone was nearing the edge at the same time and I was no exception.

I’m pretty sure that Chandra came first from the screaming blowjob that he was getting from Susan. He wasn’t even finished shooting when Susan raised her head off of his cock and started screaming through a powerful whole body orgasm. The effects of which caused me to cum hard with my cock buried deep within her womb. As her orgasm eased she slowly collapsed onto the bed with her arms and legs spread and I went with her.

As we went down, I looked over towards Bob and Jackie just in time to see Bob pumping Jackie’s ass full of his seed. Jackie had his legs pulled back and his cock was shooting all over his chest and belly.

We all lay there like a group of hogs in a mud puddle, so satisfied that we didn’t want to move.

I slowly slipped out of Susan and said to Bob, “You want to switch Bob?”

He just smiled, pulled out of Jackie and we traded places.

As Bob slid his face between Susan’s cheeks I slid up to Jackie’s spread legs and we both started licking them clean. Chandra wasn’t left out since Susan’s face never left his crotch so when Bob started licking her she licked Chandra. Eventually everyone was as clean as a tongue could get them.

Jackie and I helped everyone find their clothes and get dressed. Bob and Susan said they would drop Chandra off at the club so he could get his car. We all hugged, kissed and said goodbye promising to do it all again next year.

As soon as the door closed, Jackie and I both stripped completely and got in bed. We hugged and kissed for a while then we spooned, me behind him, with my cock laying between his cheeks.

I woke about six hours later in the same position, only Jackie had my cock inside his ass and was pumping back and forth at a nice easy pace.

I told Jackie, “That is the best way to wake up but I think we ought to sixty-nine, so that I can taste you.”

He seemed to like that idea and we got in position on our sides and began a couple of long and slow blowjobs. We each came but there wasn’t much left after the couple of days we had. It was almost noon by the time we actually got out of bed and we still needed to shower and pack.

“Why don’t we order room service so we have time to get packed and take a shower?” I suggested.

Jackie thought that was a good idea and told me what he wanted for lunch. Then, we started picking up our clothes and separating them. I called room service and got our order placed, then we both jumped in the shower.

As you can imagine the cleaning process just re-ignited our lust for each other. We were still in the shower playing when we heard a knock on the door so I grabbed a towel and jumped out. I opened the door and it was room service with our food so I had him leave it on the table and paid. As he was leaving he couldn’t keep his eyes off of our piles of lingerie.

“Looks like someone had some fun!” he said.

Just the, Jackie wrapped his hands around me, grabbing a handful of tit in each and pumping his towel covered crotch into my ass. Then he said, “You could too if you hang around.” That seemed to be a bit too much for him and he scampered out with Jackie and I laughing hysterically.

After the room service guy left, we sat and ate lunch talking about our adventurous week-end, still only dressed our towels.

I said to Jackie, “It feels to me that if we get dressed in our normal clothes than it never really happened. Does it feel like that to you too?”

Jackie got up and took me by the hand and led me to the bed where he shed both of our towels. He then proceeded to lay me on my back and started kissing me deeply. Within moments we were caressing every inch of each other’s bodies and I never wanted anyone so much. I spread my legs and pulled them back to my chest.

“Please fuck me one more time Jackie,” I said with a tear in my eye.

Jackie slid down and started lubing me up with his tongue and saliva. After about a minute of his loving tongue work he slid himself all the way into me. He held himself in place for a minute or two while we kissed deeply with my legs wrapped tightly around his back. It felt so good to feel full and know it was someone that I was really starting to care about.

As Jackie started to move within me, I squeezed and released his back to keep the pace slow and deep. As he was pumping in and out of me our kissing went from light to full on forceful and deep tongue probing. It was during one of the forceful tongue battles that Jackie said he was cumming. He pushed in all the way one last time and I could feel his contractions pulsing in my bowels.

As Jackie was cumming down from his orgasm he asked, “Did you cum yet”

I said, “No I didn’t, but I’m looking forward to filling your sweet ass.”

He said, “I was hoping that would be your answer.” as he rolled off of me and pulled me on top of him.

We went through the same process only with the roles reversed. After tonguing his sensitive hole I slid inside of him and he put his legs around my lower back. Even though I started off slow and tried to keep it that way Jackie kept yelling, “Faster and harder, faster and harder!”

As I picked up the pace with the assistance of his heels digging into my ass we reached a near jackhammer pace before he started yelling, “Yes, yes, oh god yes!”

That in turn set me off and with one final lunge I came as hard as I ever had and collapsed on Jackie. Both of us were panting like we had run a mile and every time I had another post-orgasm contraction so did Jackie. We were a satisfied mess of sweat and cum and we both fell asleep within minutes.

At some point during our sleep, I rolled off Jackie. I woke to him getting out of bed to go to the bathroom. It was now three in the afternoon and we both needed to take a shower again and finish packing. When I heard the shower turn on, I got up and finished packing my things, leaving out what I was going to wear home. I didn’t dare go in the bathroom until Jackie came, otherwise we would never get out of here.

As Jackie walked out of the bathroom, I headed in and as we passed he smacked me on the ass saying, “Want me to join you in there sexy!”

I smiled a devious smile and said, “Not if you want to go home tonight.”

Jackie smiled back. “I know what you mean but I think we both need a rest, at least until next week-end.”

The End.

Thanks to all who have taken the time to read this series! I have received some lovely comments and some helpful story ideas.

Published 
Written by stockingluvr
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