Helping Out the Neighbour

I was happily single after a run of somewhat disastrous relationships that at least had ended before marriage. There were various reasons, one was about money, one got upset if I even noticed that there were other women in the room, one was more interested in getting mani/pedicures and her hair done than working and I can't even remember why I broke up with another one but I remember there was a lot of swearing from her when I told her it was over. I could likely have dealt with those things if the sex had been better but as much as all of them seemed good initially, it quickly turned out that having sex was either something they did to get a boyfriend but not to keep one or they were just plain boring. It wasn't like I was into really kinky sex, I just liked it in places other than the bedroom, maybe a nice blowjob occasionally (I'd go down on them regularly and loved it), some public sex or even a bit of anal.

The good news was that being single meant I had more 'disposable' income than most of my friends and I'd recently purchased a small semi-detached in a newly built neighbourhood. It wasn't anything huge, there was a reasonable kitchen, combination livingroom/dining room with a bathroom downstairs and a bedroom, bathroom and what they called a second bedroom upstairs that I just used as a storage room. After moving in, I quickly got to know Peter and Tracy who'd bought the place right beside me about a month before I moved in. Peter was similar to me, about 5'9, maybe 200lbs, dark hair and in decent shape. The only real differenced were that he only had a mustache where I had a mustache/beard and I was about 5 years older than he was. If he was a 7, Tracy was a 9. Almost as tall as he was with long/brown hair, brown eyes and an awesome smile. She wasn't huge in the boob department but what there was looked firm with noticeable nipples and the pants she wore when I met them looked like they'd been painted onto her beautifully firm ass. I eventually found out she'd set up their storage room for a small workout room and the results showed clearly in her trim, shapely body.

They turned out to be a nice, very friendly couple and on the first weekend that I was there, they invited me over for a BBQ so I didn't have to cook. It was just burgers and beer but to not have to cook and be able to enjoy some company made for a great night. By the time I went home, it felt like I'd known them for years and Peter and I had already made plans to go golfing once I'd unpacked everything and got settled.

Over the next few weeks, we'd often see each other coming or going and chatted often. I also found that the wall between our semi's wasn't all that soundproof and seeing as my bedroom was adjacent to their bedroom, I often heard them having sex. I really didn't mind and often masturbated as I listened to the two of them fucking and talking dirty. One night they'd been over for a few drinks that lasted just past midnight. When they left and I went to bed, they were louder than usual when they got to bed and the alcohol had obviously made them hornier than usual. As I stroked myself, I listened to the two of them saying how good things felt, how good the others cock/pussy felt and from Tracy there were several rounds of, "Yes, that's it! Harder...oh fuck I'm cumming again!"

Eventually, things got quieter and then I heard Peter quite clearly saying, "I'm not that drunk, keep your finger out of my ass."

It was slightly muffled but I could just make out Tracy saying, "Oh come on, both of us enjoy it when you fuck my ass, let me have some fun with yours."

"Not gonna happen, no fingers and I'm definitely not interested in having one of your toys up my ass like you keep suggesting, how about I lick you to one more orgasm instead?"

There were a couple more quieter exchanges that I couldn't make out followed by Tracy moaning, "Even if you won't let me play with your ass, the way your tongue hits all the spots in my pussy almost makes up for it."

"Almost?"

That was followed by a series of moans, groans and other noises from Tracy before I finally heard, "Alright, alright - your tongue totally makes up for not wanting me to play with your ass!"

That was followed fairly shortly by, "Fuck yes! Don't stop, finger my pussy! I'm going to cum again!"

As I lay there stroking my cock, all I could think of was her wanting to play with his ass and wanting to fuck him with one of her toys. I'd never had anything up my ass nor had I ever enjoyed porn where the girl was playing with the guy's ass but hearing them seemed to trigger something inside me and I shot one of the largest loads I'd had in a long time, all over my stomach and chest. A couple of the spurts were so strong, they hit my chin and cheek.

Over the next week, I kept having the same thoughts until one night while I was listening to them, I grabbed some lube and as I stroked my cock with one hand, I fingered my ass with the other. By the time I came, I had two fingers deep in my ass and I was wishing I'd tried anal play sooner.

Over the next few months, almost every other weekend one of us would have the other over for a BBQ or some drinks, sometimes with a few of the other neighbours as well and sometimes just us. I quickly noticed that anytime they'd had a few extra drinks, the sex that night would be louder and more intense, often with her asking if he'd at least let her try some ass play with him and the answer was always 'no'. In the meantime, I'd found that I came a lot harder if I played with my ass and had even tried a few other things that were a bit larger like a carrot and found that felt even better.

We'd just gotten into fall and they were having some minor renovations done to their upstairs when Peter came over and asked if he could use my bathroom as their water was temporarily shut off. I was just in the middle of painting my downstairs bathroom so told him to use the one at the top of the stairs. When he came down, he had a bit of a strange look on his face. When I asked if he was ok, he mumbled, "Ya, I'm ok. It's just...."

"Just what?"

"Damn, this is kind of embarrassing but I could easily hear the guys that were working upstairs at our place. Does that mean that you can hear it when we...well you know?"

There wasn't much sense in denying it so I said, "Well yes, sometimes more than others."

"What do you mean?"

"Well, it's not something I thought we'd ever be talking about but it seems the more the two of you have had to drink, the louder you are so it's pretty hard not to hear what's being said and is happening."

Maybe it was the way I said it or maybe he was already thinking it but after looking at me for a second or two he said, "Shit, so I guess that means you've heard Tracy asking for, well... some different sex?"

We'd gone this far so I figured there wasn't any sense in pretending otherwise now so I nodded and said, "Yup."

"Oh shit, that's even more embarrassing. I'm not sure why she keeps asking, it's not like guy's wants anything up their ass."

Now it was my turn to get a funny look on my face which he quickly noticed. "Or maybe it's just me?"

Now it was my turn to be a bit embarrassed, "Well, up until I heard the two of you, I'd never had anything in my ass and never really wanted to but then I got curious and when I did a bit of experimenting and found I kind of liked it."

"Wow, didn't expect that but I guess everyone's different. At least you don't think it's too weird or anything then."

"Now that I've actually tried a bit of ass play, nope, not weird at all. Who knows, you might even like it."

"Maybe, but it's not something I even want to find out if I like or not. Anyway, I'd better be getting back to see how the work's coming."

As he left, I couldn't help having the same thought I'd had for a while now and that was of what it would feel like to have a woman actually use a toy on my ass but seeing as I wasn't dating anyone, that wasn't likely to happen anytime soon. The next time we got together for a big evening was Thanksgiving and they'd invited me over for dinner. I usually grabbed some wine and beer but for tonight, I decided on wine and a bottle of nice rum that I'd been given. Once supper was done, we made some more drinks and then moved to their living room to talk and watch some tv. As the alcohol kicked in, Peter and Tracy got a bit frisky which wasn't unusual. It was good that I just lived next door because all of us were fairly drunk and at least I didn't have to go far. I was using the washroom by the kitchen when I heard Tracy saying to Peter, "Hey, once we're alone, how about we go upstairs and have some fun. Maybe the turkey won't be the only thing that gets stuffed tonight."

I was totally surprised when I heard Peter reply, "If you want your turkey stuffed, I'd love to but if you're thinking of doing the stuffing, maybe talk to Mark. Apparently, he's heard us a few times and thinks it'd be a lot more fun than I do."

"He's what?"

After a drunken laugh, Peter said, "I was over there a while ago and could hear the guys doing our reno pretty easily. Turns out the walls are a bit thinner than we thought and he can hear us sometimes and has heard you ask to play with my ass."

"Damn, that's embarrassing! What did he say?"

"Just that he heard us, started thinking about it and since then he's played with his ass a few times and liked it."

"Hmmm, maybe he can convince you to try it then!"

"He did suggest it but I told him the same thing I keep telling you, I'm not interested."

I'm not sure what else was said because as soon as I opened the bathroom door, they quit talking but that night instead of a 'generic girlfriend' in my dreams, it was Tracy standing there with the lube, vibrator and me naked on the bed.

Things were a little quieter between us for a bit but nothing else was said about her desire to play with his ass or me enjoying playing with mine but they quickly got back to normal. It was a few weeks before Christmas that Peter popped by and asked if I had a few minutes. When I said, "Sure!", he came in and I grabbed a couple of beer for us.

Not much was said until the second beer was almost done and then he said, "Mark, I really want something special for Tracy this Christmas and thought maybe you could help."

I laughed saying, "Oh ya, two guys going shopping for his wife's Christmas present. We'll come home with tools or a new snowblower instead."

That's when I noticed the look in his face and realized that wasn't what he was thinking of. After taking a deep breath, he said, "Tracy and I have been together almost 6 years and I've lost track of how many times she's asked to play with my ass and it sure as hell wasn't something I was going to discuss with anyone else but seeing as you already know, that makes it a little bit easier. This is going to sound really strange but would you be interested in your ass being one of Tracy's Christmas presents?"

He must have thought I was having some sort of a seizure because later he said my mouth just opened and closed several times and I was blinking but that was about it. When I finally managed to talk, I said, "Let me make sure I'm right, you're asking if I'd let your wife fuck my ass as one of her Christmas presents?"

"Ya, that's pretty much it. Nothing else, no kissing, no oral and definitely no actual sex."

"Well fuck! I've been asked some strange things but that pretty much tops them all."

"I'm sorry, I thought maybe it was worth a shot. How about we just forget this whole conversation?"

As he started to get up, I stopped him with, "I didn't say no, I'm just kind of shocked."

Sitting back down he said, "So you're interested?"

"Let's just say I'm still trying to wrap my mind around it. What will Tracy say/do? The last thing I want is for her to freak out when she finds out we've planned this."

"I know and I haven't quite figured that out yet but I thought I'd run it by you first. If you're good to try it then we can figure out how to make it happen."

"If we can work out something that won't break us up as friends then I'm definitely interested."

"Ok, then let's figure things out over the next week or so" and with that, he got up and went home.

After he'd gone, I replayed the whole thing through my mind a few times to even convince myself that it had really happened and it wasn't long after that before I was laying on my bed, stroking myself and imagining what it would actually feel like.

Peter and I talked over the next week or so and finally came up with something we thought would work. A few days later, Tracy knocked and asked if there was any way she could use my computer for a bit because hers wasn't connecting to the internet and she had a few things she had to log into her work and do. I said sure and pointed to where my computer was set up in the living room. "I was just on my way out to do a bit of shopping. If you're done before I'm back, just lock the door when you leave ok?"

"Sure thing, thanks!"

I did actually have some things I needed to pick up but even though they weren't urgent, I grabbed them anyway and took my time getting home. When I got there, the door was locked and she was gone. The next day, Peter caught me in the laneway and with a big grin said, "So, apparently you left some porn running on your computer yesterday!"

I just grinned back and said, "She actually told you that?"

"Not right away. When she came home, she just said 'Bedroom, now!' and we had one hell of a session in the bedroom. Afterwards, when I told her I couldn't remember the last time she was that wet and that horny right at the start, she kinda blushed and told me that she'd seen something that got her excited. I pushed it a bit and she finally admitted that she'd seen a couple of videos on your machine of a woman using a strap-on on a guy."

"Is that all she said?"

"No, she did suggest that if you were turned on by it then maybe I should at least look at some videos of it and see if it did anything for me."

"And I'll bet you said no."

With another big grin, Peter said, "That's exactly what I said, but I also told her that I wouldn't say anything to you about it."

"Got ya!"

We still got together fairly regularly to talk, relax and enjoy a few drinks. Other than catching Tracy looking at me more, everything continued pretty much as it had been. A few days before Christmas, I overheard them talking in the bedroom and when I figured out what they were talking about, I just had to put my ear to the wall so I could hear better.

"Look, I don't care if Mark likes fingers or anything else in his ass, I'm not interested in finding out."

"Please, just once. If you don't like it then I won't ask again but it's something I really want to try, remember how hot I got after seeing a couple of his videos?"

"Then maybe you should be asking him, not me. Who knows, he might be interested in letting you try."

"Seriously? How the hell would I do that? I really can't see myself saying, 'So, Mark - I accidently saw some videos on your computer of a girl using her toy on a guy's ass and Peter told me you like playing with your own so I wondered if you'd like to try it with me.' I can just imagine how badly that could go and I really doubt it's something you're going to ask him for me."

"Ok, you've got a point but let's just say he was interested, would it turn you on as much doing it to him as it would if I said yes?"

There was a bit of a pause followed by, "I'm not totally sure but considering I just got a bit wet thinking of it, yes - I think it would definitely turn me on."

Obviously, I couldn't see what they were doing but then I heard, "Damn, you are wet from thinking about it. Are you picturing him lying there while you finger his ass like you want to do to me? Maybe then when he's ready, you lube up one of your vibrators and watch as you slide it into his ass?"

"Fuck yes!"

"Damn, I can feel you getting wetter and wetter. Thinking about it turns you on that much, does it? Who knows, maybe he'd let you use that harness and strap-on you bought last year when you were trying to convince me to let you fuck my ass and fuck him with it."

"Oh damn! I'm going to cum!" followed by a series of moans and groans from her.

"Damn woman, you just squirted all over me!"

"I told you I get really turned on from thinking about it and I can only imagine how hard I'd cum if you ever said 'yes' to trying it but for now, how about I straddle your face and you can lick me for a bit before I straddle your cock and ride you until you fill me with cum?"

"Sounds good to me."

The conversation faded out but there was definitely lots of grunting, groaning and moaning before everything went quiet for the night. When Christmas Eve rolled around, we had a few drinks at their place and then I headed home...or at least that's what Tracy thought. Peter kept her occupied in the living room while I snuck around and came in through the unlocked back door and crept up the stairs. About 10 minutes later, I heard Peter say loud enough for me to hear, "I know we usually don't, but would you like one of your presents tonight?"

Just the way he said it must have gotten her interest because she said, "I'd love to!"

"Ok, here - put this blindfold on, I don't want you to guess it based on how it's wrapped."

She must have put it on because shortly after, I heard them coming up the stairs. Because I was kneeling on the bed, facing away from the door, I couldn't see them but I could easily hear them coming into the bedroom. There was no doubt when he pulled her blindfold off because the first thing I heard was a loud gasp followed by, "Holy fuck! What the hell!"

I could understand her reaction because she'd be looking at my bare ass up in the air with a tube of lube on one side of me and her harness/strap-on on the other. I couldn't tell but I was pretty sure he was grinning as I heard him say, "Well, you've been after me for years to play with my ass but that's not something I want to try. Mark's found he enjoys some anal play by himself but has never had anyone else do it to him but would like to try so I figured it would be a perfect present for you. We've already talked so he knows that it's only anal, no kissing, oral or sex."

It still took her a few seconds to get everything together in her head before she blurted out, "How long have you been planning this?"

Now I knew I heard a chuckle before he answered, "Well, remember the porn that you 'accidently' saw on his laptop because we had no internet?"

"Yes."

"I was the one that disconnected the cable downstairs temporarily so you'd have a reason to go over there."

"You sneaky bastard! I'm still not quite sure what to say but there's no way it's going to be 'no'!"

That got a laugh from all three of us before he said, "Well, I'm going downstairs to watch hockey, have fun!" and with that, he left the two of us in the bedroom.

There were a few seconds of awkward silence before Tracy said, "Please don't tell Peter but since he told me you play with your own ass occasionally, I've thought about what it would be like to play with it a few times before and I'm already wet thinking about it now."

I felt her move on the bed and when I heard a soft 'click', I was pretty sure she'd opened the lube and when I felt a cool, slick finger tracing patterns around my pucker, I knew I'd been right. Next, I felt the tip of her finger tentatively exploring the entrance to my ass. When I moaned slightly, that gave her the confidence to push a little harder and shortly after that, I felt her finger slide all the way into my ass. When it did, she giggled and whispered, "I guess I am actually opening my Christmas present aren't I?"

I chuckled too and my chuckle quickly turned into a low moan as she started slowly sliding her finger in and out of my ass. "Damn that feels even better than when I do it myself, go ahead and try two fingers if you want."