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I then slowly pushed my finger until it was buried to the first knuckle.
I gave her a moment to adjust and then I pushed in about another inch. It was obviously not comfortable for her tiny hole, but she didn't object.
When I had buried my finger as far as it would go, I inserted a second finger with the same process.
By spreading my fingers, I was stretching her A hole to accept a bigger part of my body.
Once she stopped squirming, I asked her if she was ready.
Trembling, she just moaned and nodded her head. I climbed up and aligned my rock hard dick with her little brown hole. I slowly pushed the circumcised head about an inch into her ass.
I stopped there as she shifted her body to better accept the next push. When I thought she could deal with it, I pushed in another two inches.
Anne started moaning and I didn't know if I was hurting her or pleasuring her. I did know that her nose was only inches from my sleeping wife's face.
I had nothing to go by as Anne never told me to stop. I did feel her push her ass toward me as I pushed another two inches of dick into her hole.
With one more push I figured I would be all the way in.
About half way there, I hit bottom. The last inch and a half appeared to really stretch Anne's ass to the limit.
With more tears running down her face she said to me I am ready. Fuck my ass as hard as you want and as an afterthought she said "I also want to thank you in advance for getting me warmed up for Harold."
I started stroking in and out as hard as I could. After all, I felt an obligation to get her ready for the big test.
She took the butt hole violation like a real trooper. She even started to push back to accentuate my forward thrusts.
She used her hand to spread her vaginal lips and massage her pussy while I used her anus.
She reached her climax after a few minutes of pounding, and just like Julie, she used her tight little ass hole muscles to massage my dick and bring me off as she came.
As I pulled out, she looked up at Harold and without hesitation said it was time.
If ever he was going to manage to do this, without ripping her open, now was the time.
Though I hadn't stretched her to his proportions, I had started the process. And there was still a load of my seed lubricating her swollen passage.
As I extricated myself from her hot body, Harold took my place.
He managed to insert about the first six inches before it got uncomfortable for Anne. After holding still for her to get used to it, Harold made a decision that the best way to get there was with one hard thrust.
Anne screamed so loud from the pain that she woke Sarah and set off a few car alarms in the neighborhood.
From there, Harold worked up to a fucking motion that Anne could endure.
Because of the size of her hole, the pressure on Harold's dick was incredible. He came first and dumped his load, causing her well used tunnel to send her into another climax.
When Harold pulled out, Anne joined Sarah in unconscious bliss and fell asleep curled up spooning my wife.
We let the two girls sleep it off and that also gave us some time to recuperate.
I told them of Sarah's promise to fullfill my fantacies all week, and John told us that he and Anne were talking about the doing same thing.
Julie then informed John and Harold of their "inaccurate" guesses during round one of Friday's game.
Julie looked at me and asked if I knew that I had been wrong on all three of my guesses.
You ate my pussy, not Anne's, you Fucked your wife, not me and it was Anne that cleaned you up, not your wife.
Julie then said she was certainly wrong about something also. Looking at my two partners laying there on the concrete, we certainly didn't take everything you could dish out.
Sarah and Anne rejoined the party and after they showed the guys their thanks by kissing each of their partners, we settled down to a late afternoon of more alcohol and an excited discussion of future events and ideas that we each wanted to explore with specific members of the group that until today, would have been off limits.
For what seemed to be setting the tone for future gatherings, two or three of us would head up to one of the bed rooms, engage in pleasuring and fucking each other and then quietly rejoin the group.
Over the next 4 or 5 hours we each disappeared upstairs 3 or 4 times. Someone would express their desire to have sex with any one of the group and that person or person's always seemed ready to oblige.
Since tomorrow was a work day for everyone but Sarah, we decided to make it an early evening and get ready for some Monday reality.
I don't believe anyone went home feeling anything but thrilled with the events of the weekend and the possibilities that lay ahead.
The events of the last two days were obviously taking their toll on both of Sarah and I. We said our goodbyes and were half way to the street before I realized that Sarah was stark naked.
I opened the car door as I asked her if she was aware of that fact.
She said I've been naked most of the day, and it just seemed like such a bother to dress for such a short trip.
Because of the late hour, there was no one there to enjoy the view of my naked wife, so I drove us home.
As we pulled into the driveway and got out of the car, we noticed Mr. Johnson, our 80 plus year old widowed neighbor across the street, sitting on his porch swing.
Sarah whispered to me softly, oh hell, I guess it's too late now, as she proudly lifted her shoulders pushed out her chest and headed for the door.
As she closed the door behind us she said "Remind me to pay that nosy old fart a visit".
As we climbed into bed, my conservative wife of last week said I think we have just added four part time spouses to our marriage.
She continued, it just felt so natural the way everyone accepted the sex acts between their partners and who ever their partner chose.
I said Sarah, you're the most beautiful woman in the world. I love to be inside you. I love to feel the inside of your cunt, your moisture that you produced just so you could get fucked by a big dick.
I had to admit that she seemed to have a real talent for this. In fact the highlight of my day was seeing and literally feeling Harold fuck your little ass hole.
I just want to be sure that I never lose that part of you.
She couldn't answer. She just wrapped her arms around me for a sweet loving kiss.
I told Sarah that since she still had 7 days left in her sentence, that I thought I could finish up at the office by noon and take the rest of the week off to enjoy the time with her.
I was up early the next morning and made some arrangements for her day.
Sarah woke as I was getting ready for work.
Still abiding by my nude at home policy, Sarah padded over to the toilet, leaving the door open for my pleasure and relieved her bladder before proceeded to go down and start my breakfast.
Unaware of my arrangements, Sarah was surprised when the door bell rang. Like the good little slut she was becoming, she answered the door and found John with a big smile on his face.
He said, Gary asked me to pick him up so that you could have the car to meet him at the office for lunch.
As I came down the stairs for breakfast, I watched Sarah unzip John's dress slacks, pull out his limp dick and start licking him until he was hard.
As I ate a quick breakfast, I was treated to another of her spectacular blow jobs. As she swallowed all of Johns cum. Sarah looked up at him and said good morning to you too.
I told her I had left her instructions on the dresser and kissed her goodbye as John and I headed to work.
At noon, per my instructions, Sarah was in the lobby and I got a rather awkward call from the front desk telling me my wife was there to see me.
I reminded my secretary that I would be gone the rest of the week and headed downstairs to have lunch with my wife.
Sarah was sitting as prim and proper as her clothing would allow, and somehow she managed to get up without exposing her charms.
She wrapped her arms around me and said she was sorry but there had been too much going on this morning to obey the shopping instructions I had left for her and that she would explain in the car.
I purposely waited until the four men in the parking structure were right in front of us before I opened the car door for Sarah.
As she sat, her short skirt rode up to reveal her legs right up to an inch below her hairless pussy.
As she placed her left leg in, her pussy was fully exposed and the four men just stopped to watch.
She took her time getting her other leg in and she smiled at them as if to say she had enjoyed giving the show as much as they had enjoyed the performance.
Since time wasn't an issue, I decided to head for a town about 30 miles from my office. It was known as the rough part of the city. On the way Sarah got a chance to tell me about her morning.
Sarah started with an apology for not getting to the mall to make the purchases I had requested.
She was wearing a men's dress shirt with the top 3 buttons opened and a skirt that was so small, I wasn't sure the zipper was all the way up in back.
She told me that she had borrowed the skirt from Julie but that that would all make sense when she was done describing her morning.
She told me that right after John and I left, she got a call from Harold, who said he and Julie had managed to take the day off.
Harold asked if I was available and that he needed to see me.
I thought Sarah said, maybe there had been a problem, so I said of course and that the coffee was on.
Ten minutes later the door bell rang. I was surprised to see both Harold and Julie. I was relieved to see that they were both smiling, so I invited them in.
I sat on the bar stool, still completely naked as they sat facing me from the kitchen table.
Harold complemented my outfit and began their request.
He said "It had always been Julie's fantasy to get it on with Gary and he wanted to thank me for letting that happen".
I still had no idea where this was leading as I filled their coffee cups and sat back on the bar stool, unconsiously exposing myself to our new part time spouses.
Sarah continued, as I sat there listening, Julie came over and pulled out the stool next to mine and sat.
Harold went on to say that he hoped I had enjoyed him as much as he had enjoyed the special places I had allowed him to experience.
As he took a deep breath, and seeming to be very nervous about what he was going to say, I assured him that after what we had experienced together, there was nothing I wouldn't do for him and that if he had a need, he should just say it.
Harold was finally able to say did you notice how over the last two days, all the sexual activity, even when three or more of us were going at it, all involved a man and a woman?
As I considered my response, I became aware of Julie caressing my arm. I said I hadn't given it any thought but in thinking back, I would say that his observation was correct.
At that moment, Julie stood in front of me and lifted my chin as she leaned in and surprised me by kissing me right on the lips.
She was so soft and so confident that I didn't know what else to do. I had never been kissed by another woman, but it felt so good and so right that I responded by slightly spreading my lips and kissing her back.
Like the naïve woman I am, I still did not understand what Harold was asking of me and I thought Julie was just being Julie.
Julie spread my lips with her tongue and pushed her tongue into my mouth. She took her fingers from my chin, softly running them down through the cavity between my breasts and then across my left tit to my sensitive nipple.
I was getting really turned on but I still didn't get it.
After a long couple of minutes with Julie caressing my tits and tongue fucking my mouth, she whispered in my ear that Harold wanted to watch as she made love to me.
I didn't know what to say. My juices were flowing freely down my legs, so I was obviously turned on.
I rationalized that all afternoon Sunday, every request for sex had been reciprocated. My thought process turned off as my body responded to the soft caressing of my vaginal lips by Julies fingers.
I still hadn't answered, but I willingly let them move me to the living room couch and lay me on my back. I guess my non resistance was their answer.
Harold sat watching as Julie spread my legs and licked her way up from my toes. She tongue bathed, my right foot, sucking my big toe into her warm mouth.
She massaged my leg with her tongue and fingers. Just as she reached my pussy, she stopped. I was already so wet and excited that I had lost control.
I was disappointed that she didn't lick my pussy.
Then she started giving my left foot and my left leg the same attention.
When she reached my willing pussy, she stopped again. This time she crawled up and lay on my tummy as she kissed every inch of my face and neck.
She slowly worked her way down to my chest and softly caressed each breast, as she gave them the attention that only another women could appreciate.
Then she started bighting my nipples as I moaned in pleasure. I don't know if she sensed my orgasm approaching but she decided it wasn't time yet, so she bit my left nipple really hard. With me focused on the driving, Sarah ran her fingers up my leg to get my attention. She unbuttoned two more buttons on her shirt, leaving only the last button holding her top together.
She cupped her left tit, removed it from her shirt and showed me her left nipple with Julies red teeth marks still clearly visible.
In fact, it looked like she had actually broken the skin. When I reached to massage her exposed tit, Sarah was in obvious pain from how her sensitive nipple had been abused, and not just by Julie.
Getting back to her story, Sarah went on to say that Julie spent more time focused on her tits, and massaged her sore nipples with her tongue before running her tongue down Sarah's stomach to the top of her bikini line.
At that point, Julie shifted herself between my legs. I had no choice but to spread them and allow her access to my womanhood.
I had never even considered sex with another woman, but here I was on the verge of being eaten out by another woman and her husband was sitting there stroking his beautiful 10 inch dick, just watching. Julie tenderly spread my vaginal lips open with her fingers and started licking my clit as I lost control. By the time she got her tongue into my hole, I was on my second orgasm with sweat and cunt juices flowing freely.
I kept trying to spread my legs farther apart so that Julie could reach further inside. She was pumping three fingers in and out by the time I realized she had penetrated my box with anything but her tongue.
She reached below me and forced at least three fingers up my ass and began massaging, from both sides, that little skin membrane between my two holes.
I was bucking like a stallion, but Julie kept the pleasure going until I simply couldn't move.
I noticed on the clock, that you had left two hours ago so I guessed that I had been in a state of orgasm for well over an hour when Julie got up and straddled my face as she tenderly started licking my swollen lips between my legs.
I was on my back being pleasured again by this beautiful woman that my husband had fucked so thoroughly, and I was presented with another decision.
Rather than trying to rationalize what I should do, I just reached up and started licking Julie's vagina.
I had never been this close to another woman, but I wanted to pleasure this goddess the same way she had satisfied me.
I thought of that question I had asked you while sitting and examining my vagina, about what men found so attractive with that wrinkled wet hole between our legs.
I now had the answer Sarah continued.
I had no idea what to do, so I started by sucking on her lips and burying my tongue deep in her hole. I was surprised at how I actually enjoyed the feel, the taste and the odor of another woman.
I pushed two fingers into her twat and started moving them in and out. Using the knowledge of what felt good when you ate me and from when I masturbated, I proceeded to bring her into such a screaming orgasm that she had to remove her tongue from my hole to satisfy it.
When she came down, I wasted little time in massaging her little brown hole and forcing four fingers inside.
By the time she was done coming, I knew that I would have to hurry, to get to your office.
I still took enough time to bend over the back of the couch and let Harold fuck my ass while Julie sucked on my dangling tits and cleaned the female juices from my aching pussy.
There were no goodbyes, or thank you's, Just the knowledge that we now had 5 sex partners each and the understanding that if you wanted it, your partner would oblige.
Needles to say I didn't have time to shop and I borrowed this skirt from Julie. I am ready for whatever you have planned my love.
I had planned a long lunch in a raunchy little joint just off Broadway in the worst part of town I could remember. I was going to watch as Sarah spread her legs for the patrons that were lucky enough to be having lunch late on this beautiful Monday afternoon.
I was going to let her tease them with her tits and maybe even find a dark corner to let them get a little taste of my wife's 36C tits and taste the juices that flowed from her pussy almost constantly now.
After Sarah's morning escapades, that seemed too tame.
Instead we stopped for a quick burger and a beer at a small joint that seemed OK. I did a little flirting with our middle aged waitress, but when Sarah asked her if she would let me see her tits, the manager asked us to leave.
Fortunately we had already finished eating, so we apologized and headed for this run down little theatre we had passed a few miles back.
It was showing some porno movie about little white and Asian women being fucked by big black dicks.
They had a sex toy booth in the lobby with a really old black man manning the counter.
I paid the six dollars for my ticket.
He said "we don git no white pussy in this place to offn, so I ain't gonna charge ya for the slut".
With that I quickly purchased one large and one small vibrator, a butt plug, some tit clamps, two sets of handcuffs and a box of popcorn.
We entered the theatre with the show already going and sat as close to the center as I could see in the darkness.
There was some small asian woman on the screen being fucked by a room full of black men that if their dicks were real, had to be at least 14 inches and thick as a soda bottle.
As my eyes adjusted I could see a dozen patrons, mostly sitting far apart from each other.
If I had to guess, I would have said they were all black. The two closest to us had their dick's in their hands as they masturbated in the darkness.
Sarah took all this in and asked if I thought we were safe.
I don't know if I would have felt safe at the midnight showing but this was the middle of the day.
I had Sarah undo the last button on her shirt and I let her watch the movie while I played roughly with her sore swollen nipples.
She wasn't about to stop me, but the pain from my attention was causing her to whimper and moan.
I handcuffed her wrists to the arms of the chair and I started rubbing her hairless pussy under her short skirt with the large vibrator.
It didn't take long for the other patrons to notice what was going on with this white couple that were already out of place in the ghetto.
The first guy to notice moved to the third seat on the other side of Sarah. He had an unobstructed view of not only her chest, but because of the way she was seated, her pussy was in total view.
