My Journey into Sluttiness Ch. 03

Preamble

Reading Chapter One will place this in context

Bill's lessons were finished with no more contacts between us. Jeff and I had two more love making encounters where one took place over several hours on a night that John was out of town.

Being with Jeff, cheating more and having awesome sexual pleasure I was becoming more comfortable with myself and willing to accept other invitations for a few hours of fun.

I was invited to a wedding shower for a girl friend. At the shower they had male strippers. Seeing three other cocks made me wet with hard nipples. One of the cocks was black and it hung like a horse. It scared me and excited me at the same time.

When the guys were leaving we heard, "Ladies on the table are business cards. If we pleased you call the number on the front for setting up another party. On the back are names of two clubs we dance at when we are not doing parties. Hope you come there for some fun and look over the other items of interest that might be displayed."

At the gym every time I saw a black guy working out, my mind flashed to what was dangling between his legs at the shower.

Over the next few months I was accepting guy's invitations and was having awesome sex for me at the motel up from the gym or at a guy's place. The best was when John was out of town so there was not the time line pressure.

I decided that since anal turns guys on, I would watch some I-net porn and determine if I could learn something. I then search the net and read all about it. I decided to purchase an inflatable and practice with it.

When I could be alone, I retrieved it from my hiding place and knelt on the floor with my upper torso on the bed, inserted it and increased the thickness. The first three times was difficult just from the package. I needed a lot of lubrication and lots of time to get it in. After that, the time to insert it decreased each time. I felt good that I was making progress. It was maybe the 6th or seventh time I inflated it with a squeeze of the bulb. I let out a moan as my anal ring stretched more. I would fuck myself with it so I knew what a guys cock felt like. What was unique about the black toy I had bought was that it had ridges so each thrust felt my ring flexed a little four or five times. I knew a real cock would not do that.

John was out of town for a seminar for three days. I decided to check out the stripper's work place but needed to find someone to go with. I asked one of my girl friends that had attended the shower. She was excited. She indicated she had to use the excuse of going shopping, that we would have to go early so she would be home at a decent time. I told her I had no problem with that.

It was a Wednesday night that we agreed to go. Being that the club was between us, we decided to meet at the club, in the parking lot and then go in together.

We decided to dress a little conservative in jeans and short sleeve button down front blouse. Being it was summer that was fine.

The parking lot was about 25% filled at seven already. We kept in touch with our cell so it was easy to meet. We showed our ID to the doorman and heard, "I get off at 2 if none of those inside interest you." He handed back the ID and we giggled as we entered.

There was a center stage where two guys were shaking about and then several guys were table dancing.

We placed money on the table when we desired the guys to dance at it.

I then spotted Jack, who was a stripper at the shower. I excused myself before he got to the table, went into the ladies room, wrote my cell number on a ten dollar bill and hurried back to the table.

As I walked by him dancing at another table, he winked at me. I wondered if he remembered or did that with ladies he liked.

He saw the money on the table. Fortunately Shelly did no see the red phone number I had placed on it. Jack did his thing, never mentioning the shower and moved on.

I was soaking myself hoping he would see my number and call.

My cell rang about fifteen minutes after he had disappeared. I looked at the number and it was unknown to me. I assumed it was Jack. I rushed outside so I could hear over the music. It was Jack. After my hello, Jack said, "Glad to see you again babe. I did not get your name at the shower but sure have pictured you a lot when I wank. I'm glad you came to the club to check us out further. I hope that is why you are here."

"It is Jack, curiosity getting to me."

"Babe I will be off at 11:00. I started on the early shift today. Do you want to meet somewhere when I am finished with work?"

"Sure Jack, I need to go when my friend Shelly goes. Give mea call later nad maybe we can agree on a mutual place."

"Will do babe and by the way what is your name?"

"It is Jill, Jack."

"Com'on now are, we Jack and Jill? We are too old to be playing that but we could play house if you are interested."

"Well later propose to me and maybe I will accept."

"Later than Jill."

I went back into the club and Shelly said, "Erin they have private booths in the back were we can lap dance on the guy and he is naked. I'm so hot thinking of doing that. If I do, will you? It cost twenty-five for one song. The guy also said, "For two hundred I can take my panties off, and ride the pole until he cums."

"My god Shelly, are they letting girls make themselves feel good and in the process let the guys enjoy themselves at our expense?"

"I guess so Shelly."

"Well I only have enough cash maybe for one dance."

"They have an ATM over there. I went for some more money when you were on the phone with John. How is the seminar going for him?"

"You know tired, butt after the first hour."

Some guys came by and we passed. When Jack came by I thought I would hint at a private dance and see what he would say.

I informed Shelly I was going to ask the blond guy coming our way that was at the shower.

"Have you spotted anyone yet Shell?"

"Yeah the black hair guy that was at the shower. He must have just clocked in. I have not seen him center stage yet."

"Yeah I remember him, he is hot also."

When they arrived at the table we heard, "Not interested in a table dance this time ladies."

I frowned and Shelly must have when we heard, "No cash on the table."

Shelly said, "Guys we were so engrossed in the possibility of a private dance we forgot to dig the money out."

Jack said, "Oh that is different. Let's go private then."

We stood and placed our hands in the guy's hands and headed off to the private booths. At the booth we had to pay the money. Jack received some kind of ticket for the money.

Once in the booth Jack said, "I was hoping you would pay for the whole treatment."

"One lap dance Jack and then maybe later the full treatment but I'm not paying for it when there are plenty of guys that would pay me."

"AH, Ha, shopping then; no problem babe."

When Jack downed his jock strap I noticed and forgotten how hung he was. He then said, "Jill do you want to feel it and wake it up for your lap dance."

I responded with, "Sure."

I walked into his arms, my right hand to the cock which was already expanding and wrapped my other arm around his neck. He lowered his mouth to kiss me and placed the palm of a hand flat on my mound.

"I moaned into his mouth."

By then his cock was hard and up. He said, "I will sit and you can entertain yourself. You have one song and we have 30 seconds to leave or security will come in and ask for more cash.

I wanted the cock in me but under the circumstances knelt when he sat, placed one hand under his sack to lift the balls and then opened my mouth and took the head in of his cock and swirled my tongue around it. He placed his hand son the back of my head trying to push my mouth down further but I resisted.

As I was pleasuring his cock I was having apprehension about permitting Jack to take my cherry ass as guys like to refer to it in stories I have read.

"Jill I hope later you might let me finish in your mouth or even deep throat you."

The song was up; I stood and said, "Well let's see what develops. I will be waiting for your call.

Jack escorted me back to the table and sat with me until Shelly returned. She was glowing. I knew from the smile she paid the high bucks and relished the results. I did not bring the topic up. Jack stood to give her the chair and said, "Thanks for the dance and hope we can do more later."

It was near time to leave so Shelly could get home on time. I had feelings of jealousy knowing she made herself good on a cock which was not her husband's. I was now looking forward to be in bed with Jack but still apprehension about Jack doing me anal.

Jack called and we met at a restaurant near my place. After becoming acquainted and telling him he had stirred my feelings at the shower and that John was out of town, it provided a convenient time for me to slip out of the house to watch him work.

"Jill, should we go check into a motel and make each other feel good? You have an awesome body and I have desired to shag you since laying eyes on you."

"I'd like that Jack. There is a place near here and close to my place. Do you want to follow me? Are your plans to spend the night there or a few hours?"

"Up to you Jill; I am free until three tomorrow afternoon."

"Because of the time I prefer to stay until morning for my own security or you are welcome to come to my place but I prefer you left your car elsewhere and we can pull into the garage."

"I like the idea of your place Jill and will leave my car here and in the morning you could bring me back."

Jack paid the check and we headed to my place in my car. Jack was working me up by running a finger up and down the slit hidden in my jeans. He started to open the zipper and I said, "We are here you can continue when we get in the house."

The lights were on in the kitchen as w entered from the garage. I placed my purse on the table, asked Jack if he wanted to drink and heard, "Yes, babe you as he wrapped his arms around me. His hands went to the middle of my back and my arms around his neck.

We began kissing with his hands working lower and lower until he could squeeze both cheeks in his big hands, pulling my stomach into his half hard cock.

Breaking the kiss for air, his right hand went to my mound and the palm covered my mound. I went, "Ohhhooo," as the palm warmed me up covering my mound.

"Jack let me freshen up and come with me."

I led him to the master bedroom and said, "You can use that bath," pointing to the one adjoining the bedroom. "I will be back in a jiff."

I went to the main bath, freshened, put on a mini-skirted bath robe, grabbed a couple of towels and headed back to the master bedroom.

We both entered the room at the same time; he was only in his bikini briefs with the cock extending several inches above the waist band.

When I was within touching distance, he placed his hands on the robe and pulled it open and went, "Wow!"

His hands encased the orange size breasts and squeezed them softly as our lips connected and we went to a tongue duel, stoking the flames of passion for each other.

I took my hands from around his neck, placed my thumbs into the waist band of his briefs and slowly lowered them.

I lowered my self as I was lower them and took his cock into my mouth as I continued my way down to kneeling.

I heard this deep intake of air as my mouth encircled the head.

I let the brief then fall once past his knees.

"Jill let's sixty-nine?"

My heart skipped a beat or two. I had not done that with a guy before. I knew that if he was on top he could choke me. I said, "Sure, but I get top."

"Great babe, I love looking at the pussy and asshole that my cock may get to sample. There is no more of a pleasant thing to looking at. I get so turned on seeing those inviting holes. By the way do you have some lube so you can massage my prostate as you blow me?"

What the hell was his prostate? "Sure let me grab it."

Jack was on his back, as I climbed on the bed. His cock was straight like a ruler.

I straddled his face and slowly lowered myself. When his tongue swipe my slit I went, "Ohhhhoooo."

"Mmmmm, your honey is delicious Jill make more for me."

He then sucked the clit into his mouth and massaged it so slowly with his tongue. I wrapped a hand around his cock and licked it all over, bathing it with saliva. I then opened my mouth and sucked the head into it. I mouth fucked him and tasted pre-cum in the process.

After some time I had an orgasm. During the orgasm I moaned on his cock and he flicked the clit fast. That fast flicking made the orgasm more intense then. I did more moaning.

When I had calmed down, he pushed me up at the hip bones and said, "Lube my asshole now Jill and your finger good and let's play more as you massage my gland.

I decided to do as he requested, then would move my finger around until he said something. I figured it could not be too far in for whatever I was supposed to massage.

I knew from my dildo experience lots of lube helps, so I used plenty. I never had a finger in an asshole so I was all tense at my first attempt. I pressed firmly and watched as my middle finger slowly disappeared. When it was all the way in I started to move the tip of the finger around.

I heard, "Mmmm at a certain spot each time I passed over it."

I took his cock with my left hand and returned to mouth fucking it.

I was building to another orgasm. I removed my left hand from his cock and lifted his ball. He was smooth; feeling skin was so neat. Jack was getting harder and moaned I noticed, as I touch one spot in the dark tunnel. I then concentrated with my finger at that spot as he moaned more and started to hump. I was going over the edge into an orgasm when Jack's balls seem to tighten next to his body and he thrust up so fast and hard with his hips that his cock stretched my mouth to hurting as I felt warm sperm gushing down my throat as I was in the throes of an orgasm.

Feeling the warm stuff shooting down my throat caused wave after wave of orgasmic pleasure moving over me. My nose was at his pubic bone, Jack was shaking violently and moaning on my clit and all combined to make it awesome. My god I did not know the pleasure and awesome feelings that this form of sexual play could bring to me.

When I recovered, I pulled off of his softening cock, reached for a towel to wipe my face and finger and heard, "Kiss me Jill before you do that."

I was shocked to hear that but did wipe my finger, turned and lowered my mouth with residual sperm to his. We shared the flavors of our mouths.

Let's get some sleep and play again in the morning. He spooned into me and we drifted off to sleep.

I woke up feeling a hard cock in the crack of my butt and slight humping. A hand covered a breast. There was soft warm air on my neck from his exhale. I felt so close to Jack from the awesome experience and orgasm he induced with out a cock in my pussy or ass.

I tensed after Jack said, "Do you enjoy anal, Jill."

I wanted to experience it and then with his cock as big as it was had second thoughts.

"Yes Jack I do but I think you are a tad too big and I know I will not be able to please you because of the pain."

"Please Jill, I promise to stop when you tell me."

"If you promise then I will try but please take it easy you knowing I am tense about it."

"I promise babe, promise."

He freed me from the spoon and we kissed, messed with our hands for a few minutes and then I lifted to a kneeling position.

Jack placed on a condom, found the lubricant and spread a lot on the erect tool. He then spread a lot around the anal opening and I gasped as a finger entered me; at the end of the gasp the finger went all the way with me moaning, "Ohhhhhhoooooo."

Jack finger fucked me with a single digit and I had the sensation he was spreading me. He had used his right hand for the intrusion and his left hand was holding the lube tube with his arm resting on my back.

I let out with, "Oh god," as he inserted in one shove another finger and resumed the ass fucking. I then let out with, "Mmm...mmm...mmm," each time his fingers made the inward move."

I gasped again when he shoved more fingers into me and then I was moaning with, "Ohoooo... ohoooo... ohoooo... ohoooo... ohoooo... ohoooo... ohoooo...," each time he shoved forward. The thought entered my mind that he might be trying to shove his whole hand into my ass.

Jack placed the lube tube on the bed, reached under me and played with my clit as he did my ass slowly with his hand already there.

I had an orgasm and as I was the middle of it when he withdrew his fingers from my asshole and pressed against my asshole softly with his cock. I was still coming down from the orgasm because of the finger of my clit when I felt a tearing sensation as Jack shoved his hard cock into me. I let out with, "OH god AAAAhhhhhhhhh, stop, wait. easy, go slow, ohoooo god your cock is too big."

Tears were flowing down my cheeks from the unexpected pain after all the work I had done to prepare myself.

He maintained a study push and his cock was sliding deeper and deeper. I felt my anal ring stretching wider and wider to accommodate him.

When his balls hit my thigh he stopped all movement and we remained quite except for an occasional sob emitting from me. The burning, stretching sensation was abating as we did not move.

He then did very small hip movements. It felt like with each stroke in/out, they were stirring my pain but then suddenly the pain was gone and I had the feeling of being really stretched, filled and satisfying the guy doing me.

I began to move my hips some, humping back and forth slowly against the monster cock.

Jack moved a hand under me again to play with my clit.

"You have a nice smooth ass Jill and it is tight. God it is fantastic."

Hearing those words caused my orgasm to begin to build.

"Jack, fuck my ass with that magnificent cock of your."

"Oh my god, Jack, it's deeper than before. Please fuck my little ass harder."

"Harder, please, harder; it feels soooo goood! Oh god yes! I'm going ccummmm, Jack"

"Oh Jill your ass is so tight. My cock has never experienced such a tight fit and squeeze. I love fucking your sweet tight ass Jill. Yes...Ohooooo jeez Jill, I'm UUgggghhh...UUUUgggghhh...UUUUgggghhh...UUUUgggghhhh."

"OHooo Jack I'm Ohoooooooo, Ohoooooooooo, cccccuuuuummm, ohhoo."

Jack made sure my clit was well massaged even as he was cumming. His balls were resting at my pussy entrance as his cock fired his nut juice. His body was wet with perspiration.

It felt like I had a soda can in me but the picture in my mind of being sodomized was making me glow.

Jack's cock expanding, as he was firing, stimulated ever nerve at my anal ring.

My god, I just gave my ass to a guy, not my husband, in our bed. What was I becoming?

When Jack has settled he said, "Babe that was a great ass fuck for me. I thought you were going to cut my cock off as you were cumming. How was it for you?"

"It was the best ever Jack," not wanting to tell him it was the first.

I was feeling good knowing my asshole could bring such pleasure to a guy. It also triggered the thought of wondering what all guys might do to get into my ass.

We had settled, Jack's cock softening, the stuffed feeling gradually fading away when I asked, "Jack, what percentage of girls let you ass fuck them?" Jack responded with, "Not many Jill."

We proceeded to clean up with a shower were he held me tight with his arms around me, enjoying the relaxing affect of the warm water.

After dressing I ran him to the restaurant, we had breakfast, headed for the cars after kissing each other passionately one more time before beginning a new day.

To be continued.