Should I?
 

Greetings Fans,

I am at very interesting cross-roads and I really do not know what to do. Ideas, comments, and such are welcome.

Before I met my wife I dated a girl for a significant amount time (five years) who I thought was the "one". She was a bit more wild then me, but very loyal. In truth I think I 'owe her' for opening my eyes sexually to other 'things' and I know our sexual relationship was very VERY HOT. So many stories... I know she told me up front she never wanted to marry, but I thought perhaps someday, but it never happened and we stopped dating after five years.

Less than a year later, I would meet my wife and up until now, I have not really thought about her. Jenny as I will call her found me about two weeks ago through social media. I am not a huge social media person as there just seems to be a ton of people telling you "how great there life is", "Lookie' what I made at home for dinner", and my kid just took his first shit. While I enjoy keeping in touch with friends, FB seems to be a narcissistic platform for people to either showcase that or get the "courage" to post about it when they might never have. At any rate, Jenny found me.

Our conversations back and forth have gotten less tame in the last 48 hours to the point where she asked about meeting up with my wife and I one night. Jenny, true to her comments never married and suggested a night out with dinner and drinks. My wife has seen pictures of Jenny and has always thought she was attractive and that both excites me and concerns me.

So what do I do? There is no secret between my wife and I concerning Jenny... and yet I feel it would be awkward. She invited us over to her house so she could enjoy booze without fear of driving home and I know my wife will drink and well... I am not sure I know why I am concerned. Thoughts? Ideas? I think I have too much going on in my head...
:confused:

This comes at a time when a close friend and neighbor recently told us about finding his first high school sweetheart on the internet. Seems he went to a reunion and her first husband was there. It's been like 50 years since they dated or he really thought about Sally.
But as Bob talked more about his old love the truth came out. He and his wife now collect many things. They have several life sized statues. One a cowboy that his wife June calls her lover. She hugs him and fondles where his penis would be. Bob has a very sexy looking life sized woman who he calls Sally. He actually added pencil erasers to the breasts and supposedly rubs them and tells Sally good night.
Now these are other wise normal people and actually quite religeous. We didn't know any of these secrets until Bob talked about his old girl friend and told how she was fucking many other kids in school when her and Bob were supposedly going steady.
They drifted apart and Sally married several times. Supposedly she is once again single, in her 60's, and a decent looking cougar. Bob asked us the same things. Should I go visit Sally? Should I tell June, my wife?

I say why not. You are only gonna live once and time is running out. If I had the chance I'd meet and let nature do what nature does. Also pay attention to your wife and see how she reacts. Just don't do anything to mess up your own relationship with her.

Less tame? are you reminiscing on past experiences or talking about creating new ones with or without wife? Have you and your wife played with others before? It sounds like you would like something to happen (most guy's fantasy, I know) but I don't think that is something you spring on the wife without having discussed it or have prior experience. "Hey honey an ex of mine wants to have dinner and drinks then sleep with us, what do ya say?"

Now all that being said, my high school girlfriend and I stayed friends after we broke up. It was a decision we both made due to the fact we hung out with the same group of friends and we both didn't want to make the group choose between us. I can't say there was zero tension when my wife and I started dating, felt more on my wife's part due to being the new person to the group. But that was over 20 years ago now and they are both good friends.

Model T, Dollie, and Whatnow3,

Thanks for the response. Sometimes I type something and mentally see what I want to convey in my mind and yet it fails to get typed on the keyboard. I am sorry for that and this should help Whatnow3 with the whole process.


-She and I have exchanged 'hey remember when...' and that has been "less tame".
-My wife knows Jenny contacted me and has been encouraging in talking to her since she saw her.
-I do not know if I want or do not want anything to happen.
-I think more than anything, I am the one with reservations.

However, Dollie and Model T have persuaded me to at least meet up with her and see how that goes with my wife. I am not sure what I expect or know what the hell I expect to happen, but I am game.

I will CERTAINLY post here what goes down.

Fivehole I believe often our brains and hearts see and think of things that may only be parts of our fantasies, our dreams, and what we'd like to see happen in that fantasy world. That doesn't mean the other person in this relationship are even having these dreams.
Perhaps all they want to do is meet and have a good time while talking about the past.Then again maybe they have even wilder ideas of things they'd like to do to rekindle old romances and old dreams. As mentioned, meet, have a good tme, respect your own wife's feelings, and see what happens.
It ain't easy loving someone and not hurting them. I guess all I'm trying to say is take it easy but don't be afraid to follow your instincts.
As I sit and type I sometimes know exactly what I want to say in words. Our fingers don't always write what our hearts are thinking so the words become mixed and confusing, like this !

my two pennies worth ...
 

1. I would also recommend, like whatnow3, that you discuss this over clearly with your wife. She anyways knows about your relationship so should not be difficult.... and
2. If I were you, I would not cross a certain limit when I met her again for the first time. I dont want my wife to feel that all i wanted was to fuck her again when i had the chance (which is not the case anyways).

Who knows there is friendship or tension in store for future ... but worth a try

My personal feeling would be to steer clear of this. I wouldn't go into anything like that with any kind of significant reservation. You need to think about this, your motivations, why you are concerned, and deal with your reservations before you pull the trigger on anything. You also need to have some set of understood expectations with your wife as to where things might go before you get into it.

Question
 

I hate to bring it up, but do you and your wife have kids? Because if you do, the stakes are so much higher. Going into a situation like we are all imagining, you and your wife might both think it sounds like fun, but sometimes after an event like swinging or a threesome, one or both of you has a harder time dealing with what has happened than that person imagined. And if you split up because of it, your kids will suffer, and that will increase your feelings of guilt over the whole thing.

Of course, I don't know you or your wife or really anything, but I just thought I would add this. As a parent, I have definitely not done things I would have loved to do, with the welfare of my kids in mind. I'm sure every parent on this board has, as well.

Wow, so much to say and yet nothing at the same time.

First, thank you to all the comments and suggestions. Before my wife and I even decided to meet up with her, I explained my interest and was completely truthful concerning why I wanted to meet (the truth is I was more curious and wanted to see how she was doing). Then my wife asked what she looked like and I showed her. My wife is not into girls per say, but has found a select few very "doable". Jenny was added to the list.

My reservations where because I really didn't know what I wanted and played out the evening a few dozen times in my head with what could and might happen. Everything from leaving after a 1/2 hour to my wife getting mad and us leaving after 5 minutes. I really had no idea what to expect, but my wife was curious to know about the girl before her and prompted me (or should I say us) to get together.

Of all the outcomes that I thought might happen, the ending result was nothing I could've predicted. We sat, drank, ate, and shared some stories. There lots of laughs, fun, and even a moment that both girls were very emotional on concerning me and both had tears. However, we all walked away happy. I think more than anything that was key.

This coming weekend we agreed to meet up again at a bar/restuarant and laugh so more. Details to follow because I asked the question and you all provided me with some ideas and concerns. I just think I owe the onus of responsiblitiy to provide you with the details if I ask for advise. Maybe that is me though.

For the record, we have no kids. Kids were something we entertained over the early years of marriage, but it was something we liked, but NEVER loved. I do not think either of us regrets even one bit. A lot of it has to due with co-workers, friends, and family who for whatever reason experienced single parenting, didn't want kids, but thought they did, or were 'stuck' (there words, NOT mine) in a marriage because of kids. I love my wife and I know she loves me; besides I'm a big kid.

Hey FiveHole ... great to hear back .. and that you had good fun. I guess thats the best that can happen, whatever the details, that the three of you have fun and are happy with this meeting up and getting together ! And i like the last part ... `am a big kid` :D.... Enjoy

The Conclusion
 

If you have come on here in a hopes of reading about a wild evening of filthy sex and wildness, then I am sorry to disappoint you. because it was MUCH more than that!

So, Saturday morning came quite early. I awoke to warm sensation around my cock and realized quickly I was getting awakened with a blowjob. My eyes opened I saw a bobbing motion going on under the blankets and a lock of brown hair peaking out from under it. I lifted to covers and saw Cate giving me a sexy morning BJ. She was taking care of me well and I was getting close. Then she caught me looking and stopped to talk to me.

She asked me what my expectations were for the evening... I really had nothing. I told her that I just wanted to see Jenny (Let me stop calling her "Jenny"... Jen from now on) and talk, but I DID NOT want to upset her. She smiled and said, I was never going to do that and she wanted to get together too with her. She had a blast hearing old stories and just with no stress. It was refreshing and she liked how Jen looked at me.

I questioned that "look" and Cate apparently saw a desire in Jen's eyes. I am oblivious to this, but apparently women can pick up on this shit. Who knew! At any rate, I asked her about it and she said it turned her on. I thought she was going to continue with my morning surprise, but she said, "sorry, you'll get more later". I was both sexual frustrated and aroused by this.

The day cruised right on by like most Saturday's do. At eight o'clock I was dressed waiting for my wife who was getting ready. Why is it that us men are ALWAYS and I do mean always ready before the ladies? I know why, but yet, why don't they start the process sooner so they are ready in sync with us? At any rate, I'm sitting downstairs in black pinstripe dress pants, black shoes, and charcoal gray button down shirt. I'm watching The Orioles play when I suddenly hear the sounds of heels coming down the steps. I am acutely aware of this and yet, baseball has my attention.

Cate enters the room and I look up. My jaw was hanging open as she stood there in the shortest and tightest cocktail dress I had ever seen her in. Her boobs were on display as well as it was both sleeveless and strapless. Aroused was and understatement! Her hair was pulled back and her make-up smokey. She had the audacity to ask how she looked, when she knew FULL WELL how sexy she looked to me. I still told her and she grinned heavily.

The ride over was a fun one as my wife and I talked about some of the morons we both worked with. I have no idea why, but when we got to Jen's, I almost wished we could've laughed more about the fools we work with.

Jen answered the door in an equally sizzling outfit and look. A corset-style top with a tight mini skirt and heels. Her hair was down and her red hair looked just like one of the shampoo commercials.

We went inside for a little bit and had a drink. I was going to be the "designated driver" which I though was slightly unfair, but hey... It was the smart decision with how they both looked.

First we went to dinner at an unscale local restuarant. The food was great and the wine was too. I had three glasses which I was gonna' stop at two, but was okay after the two hours we sat there. Jen and Cate however, drank at least that. When the bill came, I about shit my pants. $289.40 (It was seared into my head) for the wine and food. Jen scooped the check out of my hand and paid for it before I could even object.

We got up and the girls were both giggling about things. Somewhere on the way to the car Jen asked about going to a club so I took them down the main drag that had clubs. We cruised by three times because they kept laughing (definitely alcohol related). Then Cate settled on a place and we parked and went in.

I am not much of a dancer, but they both got me out on the floor to dance. I have not had two hot women ever dance that close to me. Cate at one point slid my hand between her legs and I felt her wetness. What a turn on. Jen did dance pretty dirty too, but nothing like that.

At around one-o'clock we grabbed another drink and headed out. I don't remember a lot of talking on the way home, but when we got there, Cate and I were about to say, 'goodnight', when were invited in. I was about to say, "we cannot", but Cate just went right on in.

We sat down and started to talk with the girl on the couch and me sitting across from them on chair. At some point the conversation got a bit wild and I said, "Easy..." to Jen.

Jen without missing a beat said, "You mean to tell me you'd not be interested in seeing me kiss Cate?" I was speachless and then then Jen leaned in and planted on Cate's lips. Cate neither backed away or turned away, but instead kissed her back. The kiss seemed to go on and on and then suddenly Cate's hands were on Jen's chest. She was massaging her boobs thru her corset.

I sat in awe watching them and then Jen pushed Cate back and started to kiss her neck and ear along with always going back to her lips. They were flat out making out heavily and I just sat and watched.

Naturally I was aroused. My hard-on was getting more and more stiff as I watched them kiss and hearing my wife moan softly was so incredible to both see and hear. To my knowledge I had never known Jen to be interested in girls past kissing, but this seemed to be intense.

Jen slowly went down past Cate's neck and pulled her top down revealing her boobs. I watched as Jen sucked and tease her nipples and boobs. Both boobs seemed to pop out of her dress as she lay there. Those 36C's just beautifully on display. I watched as Cate pulled Jen back up and they started to kiss again. It wasn't long before Jen was back down on those boobs and Jen was running her hands through her hair.

About 15 minutes past and Jenny slowly slid down and lifted Cate's skirt up and started to kiss and lick around the edge of her thongs. God, that had me so hard watching it. Cate arched her back and Jen's tongue slid in as her red hair hid what she was doing. I just watched Cate and she was definitely enjoy it. Cate would eventually look over at me and mouth the words, "Fuck" as I found myself touching myself through my pants.

Cate went back to enjoy it and I saw Jen remove Cate's thongs ever so gently and begin to do her work again on her. I saw Cate's chest start to go up and down erraticly and knew she moments away from an orgasm. Sure enough, I was not wrong as she moaned through and orgasm she got from Jen licking. Jen did not stop and just continued.

I watched feverishly and then noticed that Jen was touching herself while she licking my wife. I could see her bare ass as she had slid up her mini skirt and moved her underwear to the side and was fingering herself. That was extremely hot and I watched her. She gained some momentum and started to touch herself with the speed of a girl who was close. I looked at my wife who had basically move her dress to be a towel wrapped around her stomach.

Jen suddenly moved up and kissed Cate as I saw her convluse into an orgasm of her own. Her head looked to the ceiling as if there was the answers on how to win a million dollars up there. Then she collapseed down Cate's boobs and started to breathe heavily.

Cate pushed her gently back and had Jen stand-up. Then she removed her dress completely and pulled off Jen's mini-skirt/underwear. I really never got to see what kind of underwear they were to be perfectly honest. My wife kissed her heavily as she was naked in heels and Jen was bottleless showing a red landstrip. Cate then slowly pushed her down and began to kneel between her legs and lick. Jen's eys rolled up as she justt enjoyed the licking and I saw movment below my wife's fine ass. She also was touching herself.

Jen's eyes were focused on Cate who was uisng both her mouth and her tongue to play with her pussy. I watched both Cate's ass and head go while alternating to look at Jen was enjoying this immensely. Cate's rubbing finger inserted itself into her pussy and she arched her back as she did things to Jen which I have no idea about.

Jen soon could take no more and started to make short and soft cries that finally made way to an orgasm (number 2!). Cate had orgasmed just before this from touching herself and I sat there rubbing my throbbing cock through my pants.

There was more of this and then, a "okay, ok, ok, ok, oh...oh..." and then a whimper as Jen hit another one soon after (number 3!). Jen looked up and saw me sitting there finally and started to undo her corsetted top. Then without warning she let her boobs fall free from it. Massive 36D's that begged for more attention or that from me.

Just like in a porn, Jen looked up at me clearly enjoying the work of my wife and said, "why don't you get behind her and let's see how hard she works when she has you licking her." I needed a sign from my wife that she wanted it and then "a butt wiggle" told me 'GREEN LIGHT'.

I stood up and took off my shirt and tossed it on the chair. Then I laid down on the carpet and went down underneath Cate's dripping pussy. I gave her an orgasm almost immedtiately and then one soon after that which was either three or four total. WOW.

I was licking Cate heavily and then felt Cate lift off me and I looked up to see her stand soon after. Apparently, they enjoyed wht they gotl. I heard Cate say, "Get up here." and I didn't have to be told twice. I stood up and then both girls dropped down and started to remove my pants.

When I was completely naked like them. They both took turns deep-throating me with incredilbe force. I really ENJOYED it. While one sucked on me the other would do things to my balls. Good god that felt good.
But soon it ended when Jen wanted it in her.

I lifted her up and put her doggy style on the couch and proceeded to enter her as Cate watched and masturbated in the chair I had once been in. Upon entry she was very wet and came twice while I was in there. She did say things like "Fuck Matt, you are so far in!" Which turned me on and yet I hoped Cate was not mad. she wasn't.

I pulled out of Jen and she needed a second to catch her breath as I pushed myself onto Cate and really gave it to her. She was equally wet and felt so incredible. At this point she just enjoyed it and I know I gave her a solid orgasm before I needed to sit back in a chair because my knees were hurting.

I sat down still erect and both girls came over to suck on me if by command. Cate started, but soon let Jen have a go. Then I watched Cate drop down a little and go for my nuts as Jenny hand pumped my cock. It was finally then that I realized both girls were drunk. Both of their forheads had some 'shine' that you only get from drinking. Jenny's brown eyes gazed into mine as did Cate's green eyes. I looked at Jen who started to say, "Give me it... Shoot it! I want it now!" Cate's tongue was circling my balls as Jen pumped and at some point she hit the spot. Then I knew I was ready.

As I grabbed both arms of the chair I was in, Jenny pumped down on my cock sending a shot of cum up into the air that splattered back onto Cate's face. The shot lifted out of my cock at least a foot and landed in her hair, on her cheek over an eye and maybe even lower. Then Jen decided she wanted to swallow it and opened her mouth to collapse onto my dick as she pumped again. However, before she could clamp onto me, I blasted another shot which hit her right on the nose. IT hung on her nose she sucked down on me. I know I blew a massive load but closed my eyes and only slowly opened to fel just a hand jerking me up and down and both girls kissing with cum dripping off them. I can honestly say I've never came liek that before and yet I never really saw it. I felt wiped out and so relaxed.

We ended up cleaning up and staying the night. Right after the shower, I was ready to go again and ended up having sex again with them both. Although I think I came in Cate at the end. It was all a blur. In the morning, we said goodbye with a kiss from Jen for each of us. Cate's was on the side of the lips and Jen went for a wet on the lips one.

WOW. I never imagined that could happen and hope you all enjoyed it.

A great story. I really did not expect this to happen. So much happened then that my wife would never do to this day. She's just not into women. Her and her girfriends had used toys on each other years ago, fondled boobs briefly, and even kissed more like a friendly kiss. But that's all. She's even shared my cock with other women.

You are not the only one ModelT... Believe me... I had no expectations or thoughts of this... I merely thought it was going to be a fun night... Turns out, I had no idea how "FUN". My wife isn't necessarily into girls, but it did happen and I won't complain. :):D

awesome !!!

Hey, Five Hole.

Any chance I know this girl!:D LOL!

Now this is getting interesting! :)

I read post #11 over again. What a reuniun!
It's true we don't always know what women will or won't do!

That is pretty responsible for you two. Many people have kids because they are supposed or "oops". I like to tell people don't get married until you're over 25, don't have kids until you've been with each other for 4~5 years - built up a lot of romance and trust. (like date for 2 years, married for 2 years, then a kid or two).

I wasn't planning on having children with my wife, as she wasn't supposed to get pregnant - I was already 40 and have done my share of changing dirty diapers for EX-GFs of the past. So far, after 5 years together and 2 with a kid - while we can't quite do as much kinky - party things and have to have a baby sitter to do things, we've yet to feel we're STUCK with kids. And of course, with people like that - why do they have 2 or 3 of the little shit-factories?!

PS: Yeah, we posted our first baby shits on facebook! ;)


Not really... but other things, that are cuter.

WOW!
 

Ah... Maybe!!!??? Welcome aboard! Call me tonight!;)

Well, I wanted to say that "FIVE HOLE'S" recollection of that night in question was fairly accurate! I have a lot of fond memories of us dating, but I am so glad he met Cate. She's a lot of fun and I think I will be seeing more of them down the road.

I have not decided if I will post or not, but I have given Matt the OK to post about me. Hopefully this means I will see more of him, his package and Cate. So, Mr. FIVE HOLE the next move is yours! LOL!

Wow, great story. Sounds like what I hope will happen to me soon with my wife and the woman who took my virginity. She is in FLA with her husband and I'm here in MA with my wife.

Jenny Red,

You surprised me and Cate by joining, I didn't think this would be your cup of coffee!

So, tonight we'll meet up and I'm looking forward to it. I don't know what all is planned, but Cate told me I'll be having a great time. I gotta' say... I'm HIGHLY interested. See ya' soon and I'll definitely be posting about what all happens! I mean, if that is okay with you!?;)

Good luck five hole. Life is full of surprises. We've had a few of our playmates join this group and a bike site I am on. But so far none has added any stories or been willing for me to share any more of the adventures we had with them.
Some people don't want to share with the world and that's okay. This is why I don't use their photos or real user names. Sometimes getting all the facts does get confusing.
We'll all be looking forward to your next adventures with jennyred.

Currently writing our last encounter. Stay tuned. Not sure if I'll post it here or a new thread. Sorry for the delay!:D