Trailer Trash Pt. 08

I came back to the office. Jake had on a fresh white button-down shirt and a jacket.

Jake said, "My gawd, that is gorgeous on you. We need to have more reasons to celebrate. You are a goddess."

I wrapped my arms around him and we kissed deeply. I was vibrating all over.

Thursday night after Randy and Cherry's finals. This is told by Cherry

I finished with my last mid-term at one. I had a very romantic place picked out. Not for the food but because it catered to people wanting privacy. One of my fellow students told me all about it. It was all booths with three high sides that allowed for plenty of privacy, dark lighting and servers that were observant of the needs of lovers.

I was all tingly with anticipation. Not only did I have the afternoon free to think about the night but it had been three days since I had seen Randy. And I was randy. I decided to drop by Teddy's and pick up something special. With Teddy's help, we decided on a black loose-fitting halter top that allowed easy access to my breasts from any direction. The back was open to the waist where a string wrapped around the waist. The string held two four-inch stripes of material draped over the breasts. It left most of my stomach exposed and back completely bare to the waist. We added a white Lycra micro tube skirt. The skirt was ten inches wide and had to be positioned about three inches below my navel to give me sufficient cover of my genitals and not get arrested. We added a white micro thong that barely covered my labia. I wore a pair of black high heels that Sid had given me.

I top it off with a lot of makeup. Randy was beside himself when he picked me up. I thought he was going to fuck me on the spot but I took control.

"Down boy. Look but don't touch until Miss Cherry permits. But I take it that it is not too much. This place has a reputation of allowing almost anything. From the description, I think this is the typical dress."

Randy slobbered, "Miss Cherry no one can beat you for desirability tonight. I am already being a very naughty boy."

I smiled and said, "Let's go. We need to talk about our finals and your reward. I know you did well."

At the restaurant, it was exactly as people had described. Darkly lit and the booths were very private. It looked like seven was a popular time as there was a line to be seated which gave me a chance to see how other people were dressed. My dress was average from what I saw of the females in front of me. The most outrageous was a girl dressed in a thin black push up lace bra and a black tiny thong. All she had to cover it was a very thin four-inch white strip of material that was held in place over her Mons Pubis by a white string that wrapped around her and tied in a bow in front. The material didn't even hide the tiny thong in front and you could clearly see the string of the thong buried in her ass cheeks. I would guess her to be a C-cup which she showed most of. The guy she was with was fondling her ass while they waited to be seated. Randy was staring and breathing hard. He had his arms wrapped around me.

After they walked away I said, "Well, I may be overdressed."

Randy said as his hand sneaked down to my ass, "You are perfect."

I let him get a quick feel but then said, "Did you get Miss Cherry's permission to feel her ass?"

He quickly moved his hand and looked down, "I am sorry Miss Cherry, I couldn't help myself."

"You will get your punishment later for that infraction."

"Yes, Miss Cherry."

We were shown to our booth. As we walked through the dark room you could hear the various sounds of sex. There were moans, whispers, slaps, licks, smacks and many different ministrations of lust. As my eyes got accustomed to the dark, you could see lots of flesh, naked breasts, butts and other body parts shining in the dark. It was however very difficult to see people's face and I liked that.

As the maître d seated us a small older woman appeared, "This is Alisha, she will be your assistant tonight. Not only will she serve the food but she is here to assist you in other ways."

I asked, "What do you mean?"

The maître d said, "We want you to have a romantic night here at Costello's Hideaway. If you should need any kind of assistance Alisha can handle it. Alisha will explain."

Alisha was dressed sexy but not overtly. Alisha said, "Hi, can I start you with something to drink?"

I said to Randy, "Let's get a bottle of white wine. You pick it."

Randy ordered a bottle. He knew a lot more about wine than I did.

When Alisha came back a couple was seated at the booth opposite us. I looked up but it was too dark to see anything but a statuesque woman dressed in a red halter dress showing lots of leg and breast. The man was a spark plug of a man. After Alisha poured our wine and we ordered she went to take care of the couple.

I said, "Now tell me about your week."

Randy said, "I have seen all my grades and ...".

He paused long enough for me to say, "Well, continue."

He took a big gulp of wine, so I did also and said, "All A's and what more, top of the class."

I wrapped my arms around him and kissed him very deeply. I came up for a minute to whisper in his ear, "You can feel Miss Cherry's chest if you wish."

He whispered back, "Really."

I said, "Until she says to stop."

Randy smiled and slipped his hand under the baggy material over my right breast. I was sure no one could see.

I said a little too loudly, "I am so proud of you." Then more quietly, "You won't have to wait long for your reward."

I reached under the table with both hands and unzipped his trousers. I pulled out a semi hard phallus. He continued to rub by breast as I stroked his member.

Randy said, "Oh Miss Cherry that feels so good. I have missed you the last few days."

"Oh, my sweet boy, I have missed you also. Seems like forever. It feels so good to have your hands on my chest and your penis in my hand."

Randy while breathing hard asked, "Do you know how you did?"

I said as I sipped wine and gently messaged his penis, "I do. I made...". I paused like he did.

Randy laughed as he said, "Touché. Continue."

I sipped some more wine before I said, "All A's and top of the class."

Randy hugged me with the arm not squeezing my breast and whispered, "I am so proud of you. Let's toast."

We clinked glasses while he continued to massage my breast while I caressed his penis saying, "Congratulations."

We both drained our glasses. Randy said, "We are really good for each other. Don't you think?"

I said, "I do."

Alisha came with our salads. She refilled our glasses and asked if there was anything else we needed. We didn't.

I could feel his penis straining against my hand and I didn't want to wait to give him his reward. I said, "I think you need a reward right now. You eat your salad while I take care of your first reward."

I slipped under the table. It turned out to be roomy under there. On my knees, I unsnapped his trousers, slipped them down to the floor, spread his legs and took his penis in both hands. I kissed the tip, slowly working my way down the shaft. With both hands wrapped around the shank, I sucked the head like an ice cream cone. Randy was very excited. He already had precum.

I could hear Randy alternating between munching and moaning. I knew this was good for him. After a long period working half his penis in and out of my mouth, I pressed the whole thing in. I heard Randy gasp. I slipped my hands under his balls and gently rubbed while I slowly took his penis in and out of my mouth. I was so proud that I could take all of him. I knew I was getting better at this.

As Randy ate, I ate Randy. His penis felt so good. I removed my thong and plunged my fingers into my wet pussy. I know Randy could hear the sounds I was making. I was sure he knew I had shared in his reward.

It wasn't long before I could feel his hard member getting ready to explode in my mouth. This time I timed it perfectly and caught most of it. I felt just a little of his juices running down my chin. I decided to leave Randy pants around his feet and carefully returned to my seat by him. I kissed him.

I said, "Taste anything."

He smiled and said, "I taste myself. Oh, my gawd that was a terrific reward and not a bad salad. Don't you want to eat yours?"

I said, "I do, I am starved."

Randy said, "I believe Miss Cherry deserves a reward. May I give her a reward for her accomplishment."

I smiled, "You may. I am ready. Let's say two orgasms for now. More later."

He said, "Sounds fair. About right for when the main will arrive."

Randy slipped under the table. I had slipped my white tube skirt to around my waist and used the table cloth to cover myself. I didn't know where my thong went and didn't care. I started on my salad and wine. Randy's hands spread my thighs apart just enough to give his head room to caress my genitals with his tongue. He gently stroked up and down my slit from asshole to Mons Pubis. I had slipped to the edge of the seat to give him all the access I could.

I almost had my first orgasm with the first stroke of his tongue. It was difficult to eat but I thought I could make it last longer if I did. He stroked my pussy lips so gently with his tongue I moaned from the pleasure. When he pressed his tongue into the clitoral hood I had the first orgasm. Now I really did moan very loudly. I could feel my juices flow all over myself and Randy's face. It barely slowed Randy progress. He continued to work to get the second orgasm.

He sucked my labia into his mouth and released it. It felt a little like he was doing to me what I did for him. I was now close to the second orgasm. I was making no pretense of eating when I heard Alisha say, "I am going to hold your meals for a few minutes. Think you will be ready then."

For some reason, the words wouldn't come out of my mouth. Randy didn't stop his working his tongue into the depths of my pussy. I managed a nod and weak, "Hum, ah."

Alisha refilled out glasses, and took our salad plates. Now that I could concentrate on my pussy, I knew it wouldn't be long before a second huge orgasm would come. I could hear the lady at the table across from me and no doubt she was having a big one. I could just make out the silhouette but it was obvious she was sitting in his lap and had a penis stuck in her. The angle of her hips made me think butt not pussy and I could hear a faint hum. For some reason, the moans seemed familiar.

Suddenly, I had a second small orgasm but I knew a big one was coming. I said, "Keep going. I have a big one coming."

I then heard a loud extended, 'Ohhhhhh' coming from the woman in the table across from us.

Randy redoubled his effort. He pulled the labia apart and suck his tongue and a lot of his mouth in my gaped soaked open pussy. With my clitoris extended for him to take between his lips and gently lick it with his tongue. That did it. I started an orgasm I knew would last a while. And I couldn't help making noises. What went through my head was the scene from When Harry Met Sally where Meg Ryan faked an orgasm in the restaurant for Billy Crystal. Only this was most assuredly not fake. My eyes were rolled back and I was barely conscious from the extended orgasm.

Then I heard a loud, "Cherry!"

Merilee continues her description of the night at Costello's

We got to Costello's a little after seven. Getting out of the Hummer put on a nice show of butt and pussy flesh. I was getting used to that. The valet at Costello's was sure attentive to help me get out. I think he enjoyed my show.

As we walked in I whispered to Jake, "You are going to have to get a new vehicle if you expect me to wear these outfits. I just mooned everyone."

I felt a hand touch my inner thigh to feel the wetness already there as Jake said, "Oh, the evidence is you actually enjoy it."

We were quickly taken to our table by the maître d. He said, "Your server will be Alisha. She will be with you as soon as she is finished with that table." He pointed to the one across from us. I couldn't make out much but shadows. "Can I get you something?"

Jake said, "We are celebrating. What would you like Melons? Champagne?"

I said, "No, I want Chardonnay."

Jake picked a wine. Just then Alisha finished with the couple across from us. I couldn't make out their faces but it was clear they were in a romantic mood. Alisha said, "I got it."

She soon came back with the wine and a beer for Jake. We ordered oysters on the half shell to share as an appetizer.

Jake raised his glass as he said, "Here is to your good start with Gannon Security. I am so glad you are with us."

I smiled big as we clinked glasses and we drank. Jake reached below the table and found my naked pussy lip. He rubbed across my open thighs several times to give me some nice stimulation. He took a big gulp of beer, reached below the table, I heard his zipper unzip as he let his trousers drop to the floor. His expression never changed. You would never know he was now naked from the waist down. He placed his hand on my waist, lifted me up, and lowered me on his member. His aim was perfect. His penis slipped into my vagina with one try in the dark. He was very strong and accurate.

Jake said, "There, that's better."

I said as I wiggle my rear end to seat his penis as deep as possible in this position, "It certainly is. Thank you, Mister Jake."

Jake said, "I don't think anyone cares but don't make any overt movements."

I put my arm around his neck and rested an arm on the back of the seat. This put a breast in easy reach and I could nuzzle his neck. Jake slipped his hand under the loose material over my breast. He rubbed the soft skin of my breast and took the growing nipple between his fingers and squeezed. Even with minimum movement, I felt a bolt of electricity passed through me. I moaned in Jake's ear and whispered, "Oh, my, that feels so good. Did you feel that?"

Jake whispered back, "I did. Your pussy gave my manhood a nice squeeze."

Alisha came and delivered the plate of oysters. She refilled my wine glass and asked, "Would you like another beer, Sir?"

Jake said, "Not yet. Can you give us a little time to finish with the oyster before you bring the meal?"

Alisha smiled, "Oh part of the service is to know when to leave you to your mutual pleasure. And from the looks on the lady's face she is definitely enjoying what you are doing. Do you need anything else?"

Jake said, "A towel."

Alisha smiled and nodded as she pulled a towel from a holder next to the booth and laid it on the seat. "Anything else?"

"No Alisha, that is great. Bring me another beer where we finish this activity."

Alisha nodded, winked and left. Jake pulled me down and kissed me a long deep kiss. Another tremor passed through my body. Jake said, "Oh my, that was a good one."

I stammered "Yes, it was."

He took his hand off my breast, stabbed an oyster with his fork and slurped it down. I did the same. I then stabbed one and placed it in Jake's mouth, "Your hands have other things to do."

He smiled placed his hand back on my boob as I felt a hand rubbing my ass. He continued to rub my ass, stimulate my breast and gently slide his finger over my asshole.

I whispered, "I am a prepared slut. Let me show you what I brought." I could just reach my purse and pulled out a tube of anal lube and a bullet vibrator.

"My slut is prepared." He took the lube and worked a good portion into my open nasty hole. I pushed the last oyster into his mouth.

With my anus prepared, I raised off him, and lowered myself with his member with my feet on the floor on either side of his feet. This forced my tight skirt to my waist and left my asshole open for him. He easily slipped all the way in with one crouch. I pushed the small bullet into my wanting pussy already humming. I had a large immediate convulsion that passed throughout my body.

I twisted and wrapped my arms around him and asked, "Could you feel that even in my ass?"

He said, "I did. It seemed like your ass muscles are messaging my member. Melons this is amazing. I won't last long. Does it feel as good to you?"

His hand again was squeezing my breast and rubbing the area where his penis was embedded in my body. I kissed his neck and felt waves of sensations that enveloped my body. Everything was tingling. I stammered, "Oh yes, Mister Jake. I feel it from head to toe. Can you get off without me moving much?"

He whispered back, "Yes you don't need to do anything but stay put. In fact, I wish I could last longer but your asshole is masturbating me like crazy. You are a well-trained anal slut."

I whispered back, "Thank you Sir. I will also become a well-trained Investigative Assistant."

He whispered back, "No doubt. I want to scream it feels so good."

I said a little too loudly, "Oh fill me up. Ohhhhhhhhhhh...!!" That was all that Jake could take. He started pumping me full of his glorious jizzum. It was a large load that couldn't stay in my tight asshole. My orgasm outlasted his. I stayed wrapped around him until my body stop the tremors.

I said, "Mister Jake, that was wonderful but we are a mess. I don't want to mess up my dress. Can you towel me off as I raise up?" I handed him the towel and removed the vibrator from my pussy and turned it off. I placed it back in my purse.

"Sure, sweet Melons." I raised off him, paused as he toweled my ass and himself.

I sat next to him with my dress still at my waist and said, "I need to go to the little girl's room to get cleaned up a little. Okay."

He said, "Sure, I will have our meal here when you get back."

He was pulling up his trousers as I bent over and gave him a nice kiss. He didn't object.

I stepped in the aisle and heard a sound that was almost like Meg Ryan in the movie When Harry Met Sally where she did the fake orgasm in the restaurant. Only this was clearly real. But something was bothering me about the noises. They sounded familiar but I just couldn't figure out what it was. I stepped closer and knew that her boy was giving her cunnilingus. She was out of it. I got close enough to realize what I was seeing. This was Cherry.

I was speechless. I couldn't take my eyes off my daughter in the midst of a sexual spasm. When she started coming down from her eruptions, I came back to my senses, sort of and yelled, "Cherry!"

Cherry's eyes got the size of saucers and yelled back, "Mom!"

I yelled, "What are you doing here!"

She jumped up, knocking over the glasses on the table and yelled back, "What are you doing here!"

Cherry with her hands on her hips in a defiant posture had her skirt, what there was of it, bunched around her waist leaving her naked from the waist down.

I yelled, "You are dressed like a slut!"

She yelled back, "You are dressed just like me!"

I wiped my finger on the wet spot on her chest and asked, "What is this!"

Cherry reached between my legs and wiped Jakes discharge from between my thighs and asked, "What is this!"

I felt Jake beside me and he whispered to me, "Calm down Melons. You know what is happening here."

I took a beat and thought about the irony of the situation. I am sure my countenance went from distress to understanding and then to love. I extended my arm and said, "My baby."

Cherry smiled, pulled her skirt down to cover herself somewhat, came to me and we hugged. She whispered to me, "Sorry you had to see this. I planned to tell you tomorrow night what was happening." I could feel the tears flowing down my face.

I said, "Oh, who cares. I love you baby. And let's face I can't throw any stones."

I looked as Jake was helping Randy to his feet. I heard him whisper to him, "Buddy you need to get that thing back in your pants."