The sequence of events that led to this story started a few years after our second, and final child was born.  During those years, I became Mommy to two little boys.  I was fortunate in that Alan’s practice was doing well and I could forgo going back to work as a teacher until the boys were both in school also.  I am afraid that having two very small boys to deal with put our sex lives on the back burner for nearly three years.  By that time, Alan’s parents and the boys welcomed a short weekend together and Alan and I certainly welcomed a Friday night, Saturday, and Saturday night alone.

If you are curious about a few details of our life before, take a look at the beginning of my last two stories on Lush.

After a few weekends spent without the children, Alan and I began to revisit our pleasure in the idea of sharing me.  The initial fantasy had actually become real before the birth of our first child.  Now with some “us” time, we started the fantasy life again. 

That was a time when Craigslist Personals was fully functional and had gained a lot of popularity.  More as a lark than thinking that anything that would really happen, Alan put an ad in.

It started, with “Older Couple Looking for College Student, 18-24, +7inches”.  He included three “R” rated pics of me.  This was a first.  We had never shared any pics of me. 

We were shocked by the response.  We got over 20 responses that appeared legitimate.  Most included very impressive pics and some cell phone numbers.

Alan and I spent the next few weeks in fantasy land narrowing the field to six that looked very possible.  It was actually a big turn-on to trade pics and chat online with them.  Several of them seemed eager to go on cam while we chatted.  Like I said it was a huge turn-on for a woman that was, shall we say, thirty-plus, to watch guys in their late teens and early twenties masturbating while chatting with her and looking at her pics.  It was something Alan and I both enjoyed.

I will tell you now, it was a mistake to be so free with pics of me.  It came back to haunt us and was very jarring when it did.  It is a big part of the reason I am so guarded about what I post on Lush!!  Still, at the time it was a huge turn-on.

I will start this account with Alan driving us toward our first internet meeting. My head was swirling and I was nervous that I might throw up at any moment.  This feeling had been growing in me since we left home an hour earlier.  It all felt like a fantasy romp until I realized that I would soon be face to face with a man that we had actually arranged to have sex with me.  I say, “man”, age-wise he just barely made the definition.  He had turned eighteen just a few weeks earlier.

He was one of the first responses to our ad that we had answered.  We had been having online sex for several weeks already and he seemed very, well, polite.  He did not use crude language or ever call me by pet names.  He was a freshman at a local university and ran track.  So, he was very fit. I find that terribly appealing in a man of any age.

Anyway, as we drove toward our rendezvous, I was a little dizzy from the realization of what I was about to do.

We had agreed to meet at a hotel that we knew but did not frequent. We wanted to keep it very anonymous.  The hotel had a nice bar where we could have a drink and chat for a bit.  That would give us all one last chance to back out.

We got there a bit early and got a booth that would afford us a bit of privacy.  When the young man walked in he recognized us right away and walked over.  We all knew what we looked like, but in person, he looked younger than his 18 years.  We had ordered drinks already and Alan asked him if he would like something.  He said sure a diet Pepsi would be great.  That is when it hit me, he was not old enough to order alcohol!

He seemed as nice in person as he had been over the internet.  Alan and I had agreed that if I was comfortable with progressing I would suggest that we go check out our room.  If that happened but Alan was uncomfortable with it, he would say he needed to make sure the reservation was OK.  We actually, had already checked in.

It took about twenty minutes to finish our drinks.  Alan asked me if I wanted another, I thought about it deeply and then answered, “Sure, we can take them to our room.”

Alan’s response was, “Great!”  He ordered another round and when the waiter brought them we went up to the room. 

I will confess, that there was a lot of tension and anxiety all around on that elevator ride and the walk to the room.

When we got inside, it was clear that we all felt rather awkward and unsure of what to do next.  Jim (not his name, of course), immediately sat down on the sofa.  I had noticed that he was walking a bit oddly.  Clearly, he was feeling the moment and didn’t want it to show.  Alan seemed especially ill at ease and I began to think he had changed his mind.

As it turned out he was just being the lawyer.  Finally, he just said, “Jim this is awkward, but do you mind showing us an ID?” In that situation, that made everyone blush!!! And, it had been the source of Alan’s anxiety!  Jim fumbled for his wallet and then dropped his license, picked it up, and handed it to Alan.  Alan suddenly realized the situation and started laughing, which easily broke the emotional ice for all of us.  I was glad we had discussed the issue of bareback on the phone the night before, so that issue did not have to be tackled.

After a few moments to enjoy a chuckle, Alan pulled me close to him with my back to Jim.  He held me close and kissed me, running his hand under my skirt and up, pulling my skirt up with it.  He began fondling my bottom and running his hand between my legs.  I could feel his hardness against me.  He let me go and turned me toward Jim who was sitting wide-eyed with his hand on his very obvious cock.

Alan suggested that I go see if I could help Jim with his problem.  I was psychologically and physically ready to try for sure.  Jim was wearing rather baggy cargo shorts.  I felt his cock running along the leg and just eased the leg of the shorts up to reveal it.  I already knew he was big, but having it in my hand seemed to make it grow. (Actually, it may have made it grow!)  I was on my knees, so I just leaned over and kissed the head.  His cock was marvelous.  The head was not really mushroom-like but was plenty big and the shaft was a bit thinner just behind it but swelled nicely back from there.  I really wanted it fully in my mouth.

I leaned back and motioned for Jim to stand.  I reached up and unbuckled his belt and unzipped him and eased the shorts down.  His cock surprised me by springing rather violently upward toward his stomach when it was released.

With him standing, I really could not reach his cock with my mouth so I pushed him gently back into a seated position.  I grabbed the shaft with both hands and was about to take the head into my mouth when he suddenly stiffened his entire body, driving his cock up toward me.  I took as much of him as I could into my mouth, and suddenly felt a huge spurt of cum as he let go.  It was followed by several more cum laden spasms.  I took most of it in my mouth, but he did shoot a bit more onto my blouse and skirt.  Wow, that was a sudden beginning. 

The poor guy just lost it!!!  He blushed all the way down to his balls, then made things worse by starting to apologize for cumming on my blouse and skirt!  To go even further, his apology was directed, first to me and he called me ma’am several times and then to my husband and called him sir!  That certainly pointed to both his politeness and our age difference.

The great thing is, that I kept my hands on his cock and he never actually lost his hard-on.  I started to suck him seriously and it was great I had enough of his cum in my mouth us use it as a lube for him.  I would feel his cock start to twitch a bit and I would back off.  I wanted to keep him edging for a while.  I was enjoying a nice big, smooth 18-year-old cock in my mouth.  After several minutes, I reached between my legs and felt my pussy.  I was soaking wet and my clit and vulva were very swollen. 

Alan had removed his pants and was stroking his lovely cock and watching his wife sucking her first new cock in several years.  He sensed that I needed some help.  He came over and raised my skirt and I felt him rubbing the head of his cock along my vagina.  Oh my gosh, I wanted him in me so badly right then.  He leaned over me and whispered in my ear as my head went up and down, “I’ll take seconds today.  Let the young man have you first.  He moved back down me and as he went he removed my skirt and my panties.  I took the hint.

As Alan moved back to his vantage point, I stood up and straddled Jim.  It took a bit of effort to raise myself up enough to be able to guide his cock into me.  Oh my, it felt so good to slowly lower myself down until he was fully in me. I was so wet it was not a problem.  I just sat very still for a moment and squeezed his cock with my pussy.  I took my blouse off and Jim immediately went for my breasts. He didn’t really know what to do with them, so he just pawed them both at the same time.  Still, his enthusiasm was exciting.  I started to slowly move up and down on his shaft.  There was a bit of a problem.  He seemed to want to stay fully in me, so his hips followed me up and we really were not fucking!  I really wanted to be, well, pounded a bit. 

After a few minutes of my futile attempts to actually fuck the young man, Alan said in a voice loud enough for Jim to hear, “Jim, keep your ass on the chair.  Let Cyn fuck you.”  He must have heard.  After several good hard strokes, I felt his cock start to twitch and I knew he was close.  I raised up until he was nearly out of me, then pushed down, all the way down until I was against the base of that wonderful cock.  I was holding back my own orgasm trying to cum when he started shooting into me.  I started squeezing his cock with my vagina.  It is funny that you will think of odd things in a moment like that, but I did.  I was really glad I had done so many Kegels after our second child was born!  I felt Jim start to stiffen and try to push even deeper into me.  On his first spasm, I let go.  Within seconds we were both trembling with orgasmic pleasure.  Even after his first cum, he still shot me full of cum with four or five big spurts.  After our orgasms had subsided, I just lay on top of him with his cock in me.  Alan gave us a few minutes to enjoy the sensation and for me to rest.  He had patiently watched me take a huge load of cum orally and then another in my pussy.

When I returned to the world, I looked around Alan was lying on the bed gently holding his nearly purple cock.  I was feeling greedy.  I wanted it!  When I got off of Jim, I felt a huge dollop of cum leak out and down my leg.  The sofa was some kind of leatherette and there was a pool of cum already under Jim’s balls.   

Alan motioned me toward the bed.  He moved to a sitting position facing Jim and me.  When I got up he patted the bed beside him and I sat.  He reached between my legs and spread my vulva lips.  His three fingers were soon filled with Jim’s cum.  Alan spread it first to one of my nipples and then the other.  He pushed me back on the bed and straddled me.  He used both hands to rub the cum in and pinch and pull my nipples.  I loved it.  I started to involuntarily hump again.  I could feel the heat of his cock against me.  He leaned over and sucked first one nipple letting his lips hold it until it pulled free.  Then the same wonderful treatment on the other.  I wanted to be fucked again.

He raised up and looked down and said, “Let’s give Jim a show.  How about reverse cowgirl so he can watch me cum in you just like he did.”  He moved off me onto his back.  I moved around and straddled him. Looking at Jim, stroking a once again fully fuckable hard-on, I slowly lowered myself onto Alan’s cock.  I could tell he was doing all he could to hold back so Jim could see him fuck me.  It was so hot to be fucking Alan like that and looking at the lust in Jim’s eyes as he stroked.  I didn’t think I could hold out much longer and I knew that when I started to orgasm, Alan would.

I motioned for Jim to come over and get on the bed. I wanted him in my mouth.  He actually figured it out.  He was up and on his knees beside me.  I leaned in his direction and he snuggled a bit closer.  I grabbed the base of his cock, leaned over a bit, and started sucking him.  He quickly started holding my head, not really forcing me onto his cock, just holding it as he humped toward me.  I had sucked him less than a minute when I felt Alan start to cum.  I let go.  I had held my orgasm at bay, but no more.  I let Jim go and leaned forward to support myself with both hands so Alan could hump harder.  Within moments I was being rocked by the first wave of my orgasm.  It was like I had one earthquake when Jim shot into me, now it was mega-earthquake time.  Alan and I both stiffened and just hung there until he pumped out in me.

Before I could actually fully recover, Alan had rolled me over onto my back and Jim entered me. He had missed his first sloppy seconds and got his first sloppy thirds!  He pumped a few times and filled my pussy with its third load.  He collapsed on me and we just lay there until he was empty and a bit limp.

We had pulled the bedspread off the bed and put a big beach towel down before we started. We all just lay there, exhausted, and I let the cum leak out.

We had gotten to the hotel just before 3:00 pm and it was just after 5:30 pm now.  Discounting the 30 minutes of having our drinks and getting to the room, in two hours I had taken a load of cum in my mouth, and three in my pussy. Fantastic!

Alan got up and went into the bathroom and brought back a nice, warm, damp hand towel, and started to clean me up.  The attention of my husband was great.  While he was cleaning me, Alan suggested that we get showers, get dressed, and go downstairs to the poolside snack bar and get something to eat.  He then added, “Jim you go ahead, there is not enough room in the shower for all of us.”  Jim hesitated, looked me over, and then went into the bath.  Alan suggested to him that he be quick about it.

When Jim went into the other room Alan gave me a nice kiss and then, as he was rubbing, pinching, and pulling my nipples, suggested that if I wanted more we could finish up after eating.  He knew that I wanted to have both guys in me at the same time vaginally and anally.  He was right. 

When we heard the water turn off, he slid down my body and gave my pussy a kiss and a deep tongue and then stood up and pulled me up behind him and said, “Your turn, babe.”  As I passed Jim I gave his cock a little teasing pull and he started getting hard again.  I moved on.  I noticed that I still had a bit of cum trickling out.  I got into the shower and soaped up giving some attention to my hard nipples and giving my vagina as deep a wash as one can. It felt pretty good in my heightened state of sexuality.

When I finished, I went back into the room in a towel.  When Alan passed me for his turn, he gave me another kiss and gave his cock a few nice wifely squeezes.  It would have been nice if he had joined me in the shower, but we had decided that it would not be a good idea to leave anyone alone in the room with Alan’s pants and my purse.

I found out later that Alan had been chatting with Jim as Jim got dressed.  He had asked Jim if he was good with trying a d/p session with us and pointed out that there was no way to do it without the guys touching.  I mean that seems obvious, but Jim was clearly totally inexperienced.  Alan said that Jim started hardening again in spite of efforts to cover it. Alan suggested that I take my time getting dressed to give Jim a good show.  We had planned that I did not wear any underwear, but as I was getting dressed I realized that I was still leaking a bit of cum, so no bra was great, but I put on my normal bikini cut cotton Hanes panties.

When I came out of the bathroom, Jim was dressed and sitting on the sofa.  I am not sure if he had ever actually looked at me in toto before, from enough distance to get perspective.  He was making up for it now.  I went over to our suitcase which was on the floor and made a point of bending over so Jim could see my vulva from the rear.  I was rather proud of it at that moment. 

At that time, I normally trimmed but did not totally shave.  A couple of nights before our outing, Alan had shaved me bald.  Not only did we enjoy that experience and the sex after, but I also loved the feeling against my panties and pants when I was dressed.  Just before we left to meet Jim, I carefully touched up my shave and made myself very bald and smooth.  When I turned around, Jim had his hand on his cock.  I walked over to him and reached down and gave him a couple of tugs.  I told him that I believed that Alan had made him aware of what I wanted after we ate.  He actually blushed a bit and said, “Oh yes, thank you.”

I dressed in a thigh-length, empire waist sundress that fit my form nicely and, as I said,  a pair of rather mundane Hanes bikini panties with a bit of extra material in the crotch and a “lite days” pad.

Alan came out of the bath and got dressed as we all chatted.  The guys never really managed to become totally flaccid, and I could not tell if I were just still enjoying their cum in me or if I was lubricating myself.

Anyway, we were all dressed and a bit hungry, so off to the pool snack bar we went.  On the way down in the elevator, Alan decided to add a bit of fun to the experience.  He told Jim to refer to me as Aunt Cynthia when he spoke to me.  It is a bit perverted, but it did turn us all on a bit more.

There was quite a large number of people in the pool and the bar.  I didn’t try to hide my nipples and they got quite a lot of attention from both the men and women.  That is always fun.  Jim did manage to work calling me Aunt Cynthia several times and I like the idea of people around us thinking he was my nephew given what we had been doing and planned to do.  Alan and I had another drink, as we waited for our burgers, but poor Jim was regulated to soda. I think he was enjoying himself anyway.

It was only a short time before the food came, but I think none of us were really into a long casual break by the pool.  Although, Alan and I were enjoying the looks I was getting from the other guests.  Have I ever mentioned that I have always loved having nice breasts and nipples!

We did not stuff down our burgers, but we did not dawdle over them either.  Alan signed the check and we were on our way back to the room.  Alan picked up a couple of the pool towels as he passed them and Jim grabbed a couple too.  I think to cover up his building anticipation of what was ahead.  No one even spoke on the elevator up to the room or in the hallway.  I could see Alan’s cock in his shorts, but Jim kept the towels over his.  Very nice!

 Back in the room, I took Jim’s towels and threw them on the sofa.  I pulled him close to me and gave him what must have been his first well-done French kiss!  It took him a minute to realize what was happening.  I had grabbed his head to pull him down to me, but when he started feeling it, he pulled me in tight and pressed his cock into me as he started trying his best to kiss me back.  He was not very skillful, but the enthusiasm was there!  I moved my hands down and got them between us and pushed him away a bit with one hand and broke his grip on my head with the other.  Who knew when I would need one of the hold-breaks Alan had taught me for self-defense.  Jim was about to cum and I didn’t want it in his pants.

I pushed him back onto the bed and kind of spun him around so he was fully on the bed and pulled his shorts and undies off.  My gosh, he was close.  I was afraid to touch it!  To my and Jim’s shock and amazement, Alan came over and poured cold water on Jim’s cock and balls!  Not much, but it was enough.  Jim looked shocked and sucked in his breath.  Alan very calmly asked Jim, “You do want to fuck her, don’t you?”  Alan handed me one of the towels and I started drying Jim off and moved him further over on the bed.  I thought you are out of practice girl, you had better get in control of this guy’s cock if you want it in you when it cums, and I did.

I got between Jim’s legs on my knees.  He had not lost all of his hard-on, but I could manage it now.  I started just holding his balls and blowing on his cock head.  I was being very careful and measured. I wanted to edge him long enough for Alan to get me ready.

Alan and I had been doing anal on me regularly since we first got the hang of it a few years before, and we had often included a dildo in my vagina, but this would be the first time I had had double penetration with two real guys.

We had found out that while I loved anal once I was ready for it, it took a bit of leading me up to it.

I was aware that Alan was behind me as I started to settle down giving Jim some very slow gentle head and being careful not to push him too far.  Then, I felt Alan get on the bed behind me.  I hoped I knew what was about to happen.  It did.  Alan had a bottle of Astroglide and he began to finger my anus with it.  My gosh, it felt good.

A little note here is in order.  We consider my rectum to be a bit different than any other orifice of the body.  Alan, nor anyone else, puts any body part in it without a condom.

First one finger, gently.  Then he inserted a second finger and more Astroglide.  He was getting the lube as deep into me as he could with his fingers and using plenty. At the same time, he was stretching me.  I was having a hard time concentrating on Jim’s cock and not going too far with him.  I was experiencing the first episode of this heavenly hell ever!!!

When Alan had lubed me as much as possible with his fingers, I knew that if he followed our routine for anal there was more in store for me and I was right.  He left the bed for a moment and then returned with a small dildo that we used at this stage to get the lube deeper in me.  Alan only used it once this time.  He knew I was barely holding it together.  There was no way I could cum and not bring on Jim’s orgasm as well. 

Alan moved over to lay on his back beside Jim and me and put a condom on.  That was my cue to move over and well, lowered my anus onto Alan’s cock in reverse cowgirl.  I was totally ready for it and it felt wonderful.  It took poor Jim a minute to catch on.  When Alan was fully in me, I lay back on him and he started playing with my nipples.  I so wanted to let go, but I wanted it all now.

Alan glanced over at Jim just watching us and holding his cock.  After a few more seconds, Alan said, Jim, are you going to just watch, or are you going to fuck Cyn?”  A eureka moment occurred to Jim.  He moved over and got between Alan’s legs and literally plunged his cock into me to the hilt!  I tried to hold back my orgasm, but I was gone.

I could feel Alan filling my rectum and when Jim put his lovely hard cock in my pussy, I could feel them both.  The difference between Alan doing me anally while I used a dildo on my pussy did not even begin to replicate the experience of two nice, hard, and lusting cocks in me.  Jim was giving me full, hard strokes. Alan came on Jim’s third or fourth stroke.  He said that he could feel Jim pumping in me and just could not hold back.  He came hard enough to actually bump me and Jim a few inches off the bed.  That was more than I could take.  I was shaken by the first of several waves of orgasm.  Jim gave me perhaps three more full strokes and I think I felt him cum in me.  Whether I did or not, the second wave of my orgasm started and continued through a third.  I was totally spent!

After Jim fully emptied his balls in me he had been decent enough to roll onto his back. I just collapsed on top of a limp Alan.  As exhausted as I was, I was still having little tremors as I lay there.  Alan said that he could feel my pussy involuntarily contracting and releasing.

We all just lay there for maybe three minutes, me still lying back on Alan.  Alan said that he could feel Jim’s cum running out of me and over his balls which was a totally new experience for him!

Alan helped me roll over so he could get out from under me.  He had put another beach towel under himself when he had laid down.  He just rolled me back and I lay there perhaps ten minutes with my legs open letting Jim’s cum run out.  

I think we were all three pretty exhausted.  Jim had gone in the restroom and when he came out, for the first time since we met him, he was completely flaccid.  Alan was in pretty much the same condition.  I was very satisfied but sexually spent.

Alan told Jim that if he wanted a shower before he dressed to leave to go ahead and Jim did not protest.  As we heard Jim showering Alan asked me if I was good with that being our last session and I nodded, smiled, and ask Alan if he had enjoyed it.  He grinned and said it was a good first experience for sure.

Alan had already gotten a couple of towels for us and we wiped ourselves as clean as possible and only had to wait a few moments for Jim to return.  We told him how much we had enjoyed the experience and he certainly indicated he had done so, as well.  I was sitting on the foot of the bed and held my arms out to him and he came over and I hugged him and gave him a short kiss and a bit of a cock squeeze.  He was done.  No reaction. 

Alan said that he hoped we could do it again as a signal that this session was over.  Jim started to get dressed and Alan and I got up and I went in to shower. Alan pulled on some shorts and a shirt and saw Jim to the door and out.  We have discovered that the “send-off” is often an awkward moment.  This was no different.