Damned If You Do


"Jim will be gone for two days, and it could be that they can't get together until Thursday too. I don't know, and I sure as hell don't want to be involved in that mess either. Just trust me Drew... I wouldn't lie to you."

"I hope not. You've never lied to be before, and I want to believe you Matt, but Gloria... Oh damn. That's why you were so weird the other day when she offered to... take care of you. You'd seen her that morning. Oh my God. Oh my God."

I could see that now Drew believed me, at least partially. I had a huge load off my chest and it appeared that Drew still loved me and at least was listening to my story. I just hoped that Gloria would follow through with what I figured she'd be doing on the next Wednesday or Thursday now. If not, I'd probably be on someone's hit list for sure maybe two someone's. If Jim found out, I would possibly be on three someone's hit lists.

The next few days were tense around our home. Drew and I had sex, but it was different. Drew was holding back at times while I was struggling to overcome this sudden void that had crept into our lives. Each day brought more hope that Gloria wouldn't let me down now.

On that Monday I found out from my boss that a training class I had been scheduled to take had been moved up two weeks. I had to fly out Tuesday evening and stay until Saturday.

To say I was unhappy was a huge understatement. What with what I figured was going to happen next door this week, I felt a need to be home. Instead of being able to take a few days off I now had to fly out of town for a stupid training class.

My boss had made it clear to me what would happen if I chose not to go too.

"Matt, I know that the change in the class is bad timing, but it's the only time this year you'll be able to attend. Matter of fact, it's the last time this year they're going to give it and you have to, HAVE to have that training to continue working in your present job."

"What are you saying Robert? I'll be fired if I don't go?"

"Look Matt, this training is the next step for your move up in this company. If you aren't there, you can't move up. I need someone who's capable and able to move up. You have the capable part down, matter of fact I'm having a hard time believing you don't want to go. I apologize for the change and the shortness of notice. That's the best I can do though."

"I know Robert. I know. It's just that some things have come up on the home front and I needed to be home on Wednesday and Thursday. Guess I'll just have to man up and do what I gotta do. Sorry."

"That's the spirit. I'll make it up to you Matt, I promise."

My news didn't seem to bother Drew at all. Matter of fact she just accepted it as part of my job. In the past we'd had huge arguments about this very thing, the sudden travel with no forewarning. Suddenly an out of town trip for the rest of the week was no problem?

I didn't feel good about it, and was expecting a fight from Drew. When that fight didn't occur I was curious as to why.

"Drew, why aren't you upset about this training class?"

"Matt, I learned some time ago that your job requires you to be out of town once in a while. I know that this trip was unexpected and the class was for two weeks from now, but it will be okay. Gloria will do what she'll do, if you're right, and I'll see it. When you get home it will be settled, one way or the other. Matter of fact I think it would be better if you weren't around if she does do what you claim you saw."

"Okay. But why not want me around Drew?"

"First of all, Gloria is my best friend. She doesn't need to know that you know about her doing something like that. She doesn't need to find out that we think she's a slut, if that's what she's doing."

"Why the fuck not? I mean, I didn't plan on watching them. Matter of fact it made me kind of ill to see it when it was going on."

"How long did you watch them Matt?"

"Not long. Just enough to know that it wasn't a first time thing. For any of them."

"Okay. I can understand why you'd be ill at seeing something like that, I think. You like Jim and Gloria and thought we were great friends. Then you see that and you're put between a rock and a hard place, so to speak. If you tell Jim, you risk your friendship. If you don't tell Jim, you risk your friendship."

"Yeah, something like that."

"Then you need to understand this. Gloria is my best friend. While you and Jim are friends, Gloria and I have bonded closely. I'm not sure how I'll handle seeing her like that, and to be honest, I don't want you to be there because your being there could set a pace to drive things to a place I don't want to go."

"What? You want to stay friends with her even if she's like that?"

"Look Matt, I know you don't understand, but we are so close. I can't leave her like that, knowing that she will wreck her marriage. I can try to talk her out of doing that and remind her that Jim is her man. Barring that, I know that she'll one day need someone to lean on when Jim finds out, and he will eventually... won't he Matt?"

Drew gave me that look. She knew that eventually I'd feel the need to tell Jim everything I'd seen that day and that Jim would probably fly off the handle at Gloria. I understood why Drew felt a need to be there for her best friend, but I didn't understand how Drew could be her best friend now, after knowing what Gloria was doing when she thought she wasn't being seen.

"Look Drew, why would you want to be friends with Gloria when you know she's like that?"

"So far Matt all I have is your word, and though you're my husband and I love you, I love Gloria too. Not the same way as I love you and if she is doing what you say you saw, it will put a huge strain on our relationship too. Still, we are close friends and friends don't dump one another... ever."

"Admirable, but there are limits to friendship Drew."


I knew I was pressing too hard. The 'Matthew' thing was the first sign of obvious irritation by Drew in this whole mess. Drew has always considered friendship to be a sacred bond that is worked on and held dearly to. I had admired that in the past, but now it worried me.

If Drew kept being friends with Gloria, would Gloria rub off on Drew? Could Drew get caught up in Gloria's lifestyle and end up doing something like I had seen Gloria doing with Hal and Pete that day?

Or would Drew rub off on Gloria in a good way and cause her to re-think her lifestyle? Would Drew help Gloria to see the error of what she was doing and help her to find Jim again?

Knowing Drew, I knew that either way, I would find out. I just hoped it would be the latter instead of the former when it all settled out. Drew and I had talked about messing around on each other and we had both stated that would have the highest cost, our marriage. I hoped that Drew remembered those conversations now.

The next day I left for the training. I had misgivings, but in the end I knew that my trust in Drew was firm, and that I could only hand her the freedom to have a choice. I hoped that her seeing Gloria doing those things wouldn't be too hurtful to her, and that they'd be able to work things out. I also hoped that Drew would be helpful for Gloria instead of Gloria dragging Drew into her lifestyle.

All I knew was that I had to trust Drew to do the right thing by us. Still, there was a little voice in my head telling me to go with caution. I fretted about it all the way to the airport. Drew was driving and I could tell she was bothered by my feelings since they must have been showing.

"Look Matt, I won't do anything like those things Gloria has done, if that makes any difference to you. I love you and I can only love you. I can only make love to the person I love and that's you totally. Please Matt, don't worry about this. I'm not sure how I'll handle it all, but you don't have to worry about me. Okay?"

"Okay sweetie. I trust you. After all, we had a discussion about something along these lines a long time ago, and I know that back then you thought like I did, and extra-martial affairs were wrong. I love you Drew, I really do."

I felt somewhat better, but not totally. Temptation can bring down the most rigid and righteous person, as the bible and other written history will show. I mean, Eve was tempted into taking the apple right? Samson was brought down by Delilah. What more can I say?

I arrived in good time and called Drew from my hotel room. She was in a good mood and we had some sweet phone sex before I hit the pillow for the night. I felt better than I had earlier, knowing that Drew did love me.

We made plans for me to call her the next night around seven. After hanging up, I lay in bed and thought about what I'd seen that day. Gloria had a hot body on her that was for sure. I know that I had some thoughts once a long time ago about her but those thoughts had been short and not all that serious.

It was who she'd been doing it with that really bothered me though. I figured someone like Gloria, with such a hot body and all, should have had some real studs out there not two fat, gray haired, old men. I just didn't understand that at all.

The next morning we started the training and I discovered that it was going to be harder than I had been led to believe. I was going to be doing some work after hours in order to keep up, and while not too difficult, I could see that I was going to have some late night sessions trying to figure it all out. So much for easy classroom work and lazy days.

That night I called Drew around seven. She answered on the third ring, her voice out of breath.

"Hey Matt, how's things?"

"Good. The classes are tougher than I thought they were going to be, but I'm learning what I need to know. Why are you out of breath?"

"Oh, I was on the patio enjoying the last rays of sunshine when you called. I forgot to bring the phone out with me and had to run in before you hung up."

"So, what did you see today?"

"You were so right Matt. I apologize for not believing you. Gloria not only was doing it with Hal and Pete, there were another two men there today too. I don't know who they are, but one of them was black and the other was huge. Everywhere. I mean, huge."

"FOUR men? How'd you handle seeing that Drew? I'm sorry, I don't mean to sound pious or anything, but I told you so. Damn, four men. I never knew that."

"Matt, TWO men was too much to begin with. Four is just... slutty."

"I'm sorry Drew. I know you wanted me to be wrong and Gloria to not be doing those things..."

"It's all right Matt, can you forgive me for not believing you though? After all, you are my husband and all. I should never have doubted you. NEVER."

"It's okay Drew, I forgive you."

"Oh Matt, you wouldn't have believed it. Well, maybe you would have believed it. Three of them did her together and everything. I mean... it was nasty. Real nasty. Almost like Jenna."

I was troubled now. Drew sounded worked up, like she'd gotten turned on a bit by seeing her best friend like that.

"Uh Drew, are you all right? I mean, you sound kind of jealous or something."

"What? Matthew, how dare you. I'd never do those things. While it wasn't disgusting to see, I could never do those things, and you should know that. I mean, naked people doing it has always turned me on a little bit. Knowing that I knew some of them was way far different than watching a porn film. You know how turned on I get when watching Jenna Jamison and her studs anyway."

I had to admit that Drew had always been more of a visual type of woman than most. She'd watch porn movies with me at the drop of the hat, and later she'd wear me out in bed, or wherever else we happened to be doing it at.

"So, I don't have anything to worry about then?"

"MATT, you're pushing the wrong buttons right now, and you know it."

"Sorry. I was kidding."

"I know. So was I. Oh honey, I don't know how to go about telling Gloria I saw her today either. This is going to be harder than I thought. I have to tell her I know though. I just have to. Even if it means our friendship is in danger of being lost. I can't hide this from her."

"Drew, you do what you think is best. I'll be here for you and I'll be home on Saturday too. I love you babe."

"Goodnight sweetie. I love you too. I mean that Matt, I really do love you."

"I know Drew. Just like I love you too."

That night I was thinking about Drew and Gloria and suddenly it hit me. Drew had no other true friends at all other than me and Gloria. I had been so worried about things that I had forgotten all about that.

All the other people in the neighborhood were older to the point of being retirees. Well, almost. With the exception of Gloria and Jim, everyone was at least ten years older than us. Most had kids that were in high school. Drew and I hadn't even gotten to the point of having kids yet. Neither had Jim and Gloria.

Here I'd been worried about Drew possibly cheating on me, and she was in the middle of learning things about her only and closest friend that were not really 'good' things to know of them. I knew that I'd have to watch close and keep Drew remembering that she had me still. I'd be her rock. She was going to need one that was for sure.

The next day the classes were tougher than the day before. I struggled with some of the concepts presented and by the end of the class day I had figured out most of them and was fairly comfortable with them. I was drained though. I went out and ate, then headed to the room. After a long hot shower I called home.

Drew didn't answer the first time. Later, when it was about seven I called again. This time Drew answered promptly.

"Hey Matt. I miss you baby."

She sounded worked up. I wasn't sure whether I should be glad or worried about that.

"Love you Drew. You okay?"

"Oh baby, I'm more than okay. I'm fi-i-i-n-n-n-e."

She moaned out 'fine' and that started the hackles on the back of my neck to rise.

"Drew, are you alone right now?"

"No, I'm not baby. I'm with you."

"You're all alone in the house though, right?"

"Of course baby. I'm just practicing for when you come home."


"I've got big blue out."

'Big blue' was a fake cock we'd gotten once. It had been a gag gift I'd gotten her actually, and we'd used it a few times in our play. I knew that time to time she'd use it when I was gone out of town too.

"What are you practicing for sweetie?"

"You'll see when you get home. I'm all warmed up though. I want you naked within one minute when you walk in the door Saturday Matt. I want your hard cock poking the back of my throat while my hands pull you by your ass cheeks deeper and deeper. I want to swallow you whole baby."

I was on fire suddenly. Drew was hot to trot right at that moment and the phone sex was hot. We'd done this before too, but never had Drew been warmed up before the call and never had she started it like this.

"Oh yeah?"

"Yeah. Then after you shoot your load into my mouth and down my throat, I will suck you right back up and drag you to the couch where I'll lay you down on your back."

"Oh yeah...sounds good."

"Yeah? Well, once you're laying back I'm going to straddle your head and give you a chance to re-cip-ro-cate me. I can feel your long hot tongue licking me like you do. Oh! Oh! Uhhh!

I knew she was cumming right then. I thought that she'd come down and we'd have the rest of our talk, but I was stroking myself imagining her laying on our bed naked, working her pussy with 'big blue'.

"Oh yeah...that was good, but I want more."

Surprise number two. This had never gone two times before. This was new.

"You want more baby?"

"Oh yeah...lots more Matt. I want your tongue licking me, sticking inside me, your hard cock in my mouth while you eat me to multiple orgasm's. Once I've had enough of that I am moving off of you. I straddle your hips, your hard cock is sticking straight up. Oh...uhhhh...and I drop down on you, your cock penetrates me deep. Ohhh...uhhh..."

She was working up into another orgasm.

"Oh baby...I'm riding your cock and your hands are on my tits. My nipples are hard and you're pinching them, tugging on them. I can feel it all the way down to my pussy. So full. Full of you. Oh...Uhhhh...OH!!! UHH!!!

I couldn't believe it. Drew was having another orgasm again and so soon too. Not only that, she was worked up as much as I'd ever heard her be on the phone. I wondered briefly why, but I was caught up in the sexual tension now.

Drew came hard that second time and as she did, I sprayed all over my chest and stomach. I came pretty hard myself. It felt great, but nothing near as good as actual sex with my wife though.

While we both calmed down from the almost simultaneous orgasm's, I gathered my thoughts.

"So...how are you sweetie?"

"Missing you Matt. Missing you."

"Did you have a talk with Gloria yet?"

"No. I keep thinking about what I saw and what she must have been feeling, all those cocks..."

"Drew, you don't want to try that do you? I couldn't handle that at all. You know...'

"NO. I'm just...oh I don't know... the thought of all those cocks is enticing, but I'd never cheat on you Matt... you should know that. I'm maybe a bit jealous about Gloria, but only in what she must feel when there's more than one man inside her. Not what she's going to face when Jim finds out."

"I don't understand. You want to try multiple cocks, is that it?"

"Matt, damn you... NO. It's the fantasy baby. That's all. You never have thoughts of more than one tongue on your cock, or more than one mouth on your body? More tits, more pussy, more... I don't know... everything?"

"Well, not since I've been with you baby. I mean, a long time ago maybe, but since we've been together? No."

"You do know I'm talking fantasy Matt? I don't want to try it out for real. It's just fantasy material. Like Jenna and the studs."

"Well, you're making me a tad nervous Drew... but I think I understand. It's just the timing of it all."

"Well, until the other day Matt, I'd never seen people doing it in a group grope kind of thing in real life either. Gloria looked so... I don't know... fulfilled? Maybe?"

"How fulfilled will she be when Jim finds out Drew? How 'good' will she feel then?"

"Maybe Jim knows and is into it too Matt."

"Now you're talking real fantasy Drew. You know Jim as well as I do. He's so jealous you know he'd kill someone for even thinking about doing Gloria. You can't seriously think that he'd go for that for one second do you?"

"You're right. He'd never go for that, and neither would you. That's all right though. I could never do those things either. I just can't help thinking how it would feel and everything."

"Well, you can try those things with your next husband dear. This husband don't want nothing to do with that stuff."

"I know Matt, I know. I'm sorry. I just got caught up imagining... things. That's all. How's the training going anyway? Learning everything you need to know?"

The sudden change in conversation was probably a good thing. I was thinking bad thoughts about Drew suddenly and worry was one of the last things I needed to have on my plate this week. Still, I worried.

The next morning the trainer came up to me and told me that I was ready for the test. I was surprised.

"I thought we had another eight hours of training to go yet."

"Oh no. You're so far ahead of everyone, we talked it over and thought you'd like to get out of here early, so we think you're ready for the test. You pass, you're gone before lunch and don't have to stay the extra day."

I passed the test with flying colors and bid goodbye. I was able to catch a flight home in the early afternoon, putting me home at about four in the afternoon. The cab dropped me off and I just then realized that I hadn't called ahead to let Drew know I'd be home early.

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