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Introduction:

This is my first session with Tim & Mary.

Tim, Mary and Me!

The characters in this story were first introduced in a series called “Well, we did it again!” parts 1-5. This rendezvous occurred after part 4 of the mentioned series. This story was re-written to stand alone but reading the other series first will help the reader with some context.

It's Sunday morning, the wife has gone to church to pray for my soul. Course she wouldn’t have to save my soul, if she’d just spread her legs a couple times a month! When my wife hit her 60th birthday the frequency of our intimacy decreased to the point we have been in a 2-year dry spell. This lack of intimacy has pushed me to stray, which is sad because other than our mis-matched libidos, we do make a pretty good team.

I guess the moral to my dilemma is to be honest about your sexuality with your partner. In my case, I have always been emotionally attracted to women, so I rarely indulged my bisexual tendencies throughout my life. Until I got cut off, then my suppressed bisexuality rose to the forefront of my sexual desires. After 10 years it is too late in our vanilla marriage to say, “Honey, since you no longer have any desire for sex, is it ok for me to go fuck a dude or vice versa?” So here I am stepping out the door to have a rendezvous with a fellow I had a 3-way with at Fred’s place and his lovely wife. I feel like a total shit.

I’m as nervous as a dog during a Fireworks show. I really want everything to go well with Tim & Mary. I must reconcile myself that this could easily be a “one off”, seriously what am I bringing to the table? I’m just an old man who is more than twice their age and well past my sexual prime. Time to go, I’m just very thankful for the chance to share their unique relationship.

I arrive at Tim & Mary’s and ring the doorbell. Tim greets me at the door with a hug and passes me a small glass of Fireball, my favorite bracer. He tells me, “I know you are nervous, don’t be, we want this to work”. He leads me to living room and points me to a seat.



“Look”, he says, “I know this is going to sound weird, but ever since we hooked up at Fred’s place; I just have this connection with you. I don’t know if it is because I grew up without a father figure in my life or what, but I just find myself drawn to you. When Mary joined us at Fred’s, she pointed out that you must have very similar feelings for me. She told me how you reacted when she passed my cum to you. Only a moment’s hesitation, then you were sucking it off her tongue, she was impressed. And the way you totally relaxed when you and I kissed after I plowed your ass. Mary said she also felt a connection to you. As she put it, you were gentle with her and when she looked into your eyes, she could see you cared for both of us. Plus, she liked your pussy licking skills”, he said with a smile.

I downed the 3 fingers of Fireball before I spoke, buying some time to organize my totally muddled thoughts. Tim that first time we met at Fred’s, I liked you, how’s that for understatement? Physically, I liked everything about you, your slim hairless build, your very fuckable ass and that beautiful mushroom head on your nice thick cock. What really put the hook in me was the passion you transmitted when we kissed. I don’t know if I have ever felt so much love, acceptance, or however you describe the passion you put into that lip lock. It just blew me away.



I’m bisexual but it has always been the “emotionally, I only love women” but physically “I enjoy sex with a man”, type of bisexuality. In fact, I was pretty much just a butt slut, I never wanted to kiss a man and sucking a cock was just a requirement to get him hard enough to fuck my ass. Then you walked into Fred’s den and my priorities changed.

Suddenly, we hear Mary’s disembodied voice say,” If you guys are done professing your undying love for each other, get your asses in here! You’re keeping a lady waiting and you know there will be a price to pay for that slight.” Tim looked at my astonished face and cracked up laughing while pointing to the baby monitor sitting on the fireplace. “Mary wanted to give us time to talk things out but also wanted to listen in. She is very protective of me, and I love her all the more for it” he said.

We walked into the bedroom to find Mary sitting cross legged in the bed with her back against the headboard, with a pillow covering her crotch. Ok, nothing “abnormal” about that, except maybe the Cat woman mask, ears included and a red leather bra that completely exposed her, delightfully more than a mouthful, breasts.



She asked,” Why are you to still wearing clothes? If you two don’t step up your game, I’m just going to send Bob home!” Tim & I sent our clothes flying everywhere, I don’t want to go home! “That’s better”, she says “aren’t you curious about the surprise I have for you? Yes, ma’am we said in unison! She removed the pillow from her waist and lo and behold she is wearing a strap-on harness with a 12” black dildo that’s at least Tim’s thickness, sticking straight out.



This cute little pixie terrifies the fuck out of me, in a delicious sort of way. Tim is all smiles, like he’s remembering going a few rounds with that big boy! “Ok,” Mary says, smiling sweetly, “here’s how I would like round one to go. Bob crawl over here and start warming up my pussy and ass like you did last weekend. I want the full treatment. Remember, the more I like it, the more lube I’ll use on your ass when I drive this home, she says while stroking the monster. You really don’t want it dry do you?” “No, ma’ma”, I said. She slid down the bed and grabbed a pillow to put under her luscious hips and another one for under her head. I crawled into position and stared at the little tuff of heart shape hair above her slit, such a nice touch and buried my face into her already juicy pussy.

Mary, wasn’t going to leave Tim out, she said, “Lover, I want you to straddle my chest and feed me some of that nice cock. Remember, we’re saving your cum for later.” Ok, what does the pixie have planned? Guess, I’ll find out later, better get to work, don’t want that anaconda dry!

I followed my same pattern from last week, licked her left side labia all the way down to her anus then back up the right side without touching her clit. I made this round-trip pass three or four times until Mary’s hand came down and pushed my face into her pussy. Guess she’s getting impatient. So, I slipped my tongue between her slit and ran it down the left side labia, quick ring around her anus then back up the other side. This time I stopped at her clit and give it a few licks then back down we go.

Her hips are starting to rock a little so, I must be safe, for now. I looked up, around the anaconda, I can see Tim’s butt doing little hunching movements, I think he’s enjoying himself. I open my mouth wide and suck in both of Mary’s labia. It’s time, I bring my hands up and hold her labia open with my fingers, her clit and vagina are mine for the taking! I bury my tongue in her pussy, then lap at it like a dog, yes, her hips are moving. I remove my tongue and move up to her clit, I push her hood back and wow, I hadn’t noticed before, but Mary’s clit is about 2” long, yeah, I’m going to suck on her mini cock. Gently is the key, I stroke her clit with my tongue. I see her push Tim back and she whispers something to him.

Tim slips off Mary and disappears from my view. Mary grabs my hair and pulls my head up and says “Rim me” she releases my hair and I drop down for my new assignment. She readjusts on the pillow to get her ass a little higher. Just as my tongue goes out to explore her tight pink ring, I feel a cool liquid drip down my ass cheeks, I’ve got a pretty good idea of what’s coming next. My tongue circles around Mary anus, then I hear her hiss,” stick him”.

I feel Tim’s hands nudge my legs open, then he climbs on top of me. I feel his mushroom head searching for the opening, he applies some pressure and I feel the burning sensation as he opens me up. I move back up to Mary’s clit and start working a finger into her ass. She doesn’t stop me, instead she hands me the lube. Hint taken!

Meanwhile Tim who has been waiting for me to adjust, begins sinking is boner in me. Yes! I’ve lubed up my fingers and begin doing shallow strokes in Mary ass, while still licking her pussy. I must be hitting her just right because she has raised her knees locking my head in this position. Tim is starting to get into his rhythm, that big head allows him to pull his cock almost all the way out, “crowning”, if you will, then my ass naturally sucks him back in, he just adds a little extra push to sink it deep. I’m in heaven, face in a young woman’s pussy, two fingers plunging in and out of her ass while being fucked by her lover. My wet dreams were never this good!

I’m staring at this monstrous dildo that is swaying before my eyes, wondering, when and on who, will it be used? Should have kept my mind on my assignment. Mary calls for a change up, Tim pulls his cock out of my ass with a pop. Mary cracks up, she knows that sound. She releases my head and I start to back out from between her legs but stop to admire the view. Her pussy is slightly open, displaying her clit, delicious vagina and her slightly gapped anus, with this obscene foot long, black dildo, waving in the breeze. Only Mary could pull it off! I laugh, then have to explain my outburst. Tim looks over my shoulder and chuckles, Mary doesn’t appear to be amused.

Mary says, “Last weekend I enjoyed watching you and Fred spit roast my husband. It was so hot watching him swallow your cock while getting impaled on Fred’s impressive tool. Well, this morning, I’d like to see how well you can handle my “tool” and Tim’s beautiful cock. Are you game?” I gulped audibly, “Mistress, I will try to please you, but I fear your “tool” maybe too much for my ass.” She gave me a wicked smile and said, “I know you will please me”. Oh, shit!

Tim and I moved one of their nightstands into the open area in the bedroom. Mary placed a couple pillows on it to make it more comfortable, she really is a sweetheart, even if she is threatening my ass with a 12” anaconda.

Tim headed to the bathroom to wash up, we’re not fans of ass to mouth aside from a little rimming. While, Tim was gone, Mary told me to let her know if it is too much. “I’ll only push in as much as you can handle. See this mark on the monster? That’s Tim’s limit.” Holy shit, his ass swallowed nearly 11 inches! “This is about fun, imagination and scene playing. We’re not into the SM lifestyle.” Said the Cat Woman pixie with the 12” poker. How the hell did Tim get so lucky?

Tim returned and asked if I was ready? He said, “The main thing is to relax, get into a sub headspace and enjoy the ride. She’s damn good with that thing!” I leaned over the night table and really appreciated Mary putting the pillow on it. Mary said she was going to re-lube my ass before she introduced it to the anaconda. She pulled out a syringe that was full of lube and stuck it in my ass, pushed the plunger and filled me up with lube. Pretty damn clever that Cat Woman.

She slipped in a couple of fingers to spread the lube around then slapped me on the ass with the anaconda. “Relax bitch and enjoy the ride! Once I’m in part way, plug his other hole Tim.” A fucking military campaign to spit roast me!

I felt the Mary tease my hole with the anaconda’s head, fortunately it is not as big as Tim’s but it is hard silicone so it will not give much going in. Breathe and relax, breathe and relax. She starts pushing, my already fucked ass easily opens to accept the intruder. She pauses once the head is seated. “You ok?”, she asked. I turn my head and smile at her, “Bring it on Cat Woman!” She jabs in 6”, OOH, that will teach me to tease Mary! She nods to Tim, let the spit roast begin. He moves to my face and lifts his beautiful cock head to my lips, he rubs his precum across my lips, then says “Open up slut, this one’s for you!” Here we go!

Tim feeds his cock head in and tells me to polish that knob. I begin tonguing it. Meanwhile, Cat Woman, has been slowing sliding the anaconda in and out of my ass maintaining the 6” depth. Tim pushes more of his dick into my mouth, Mary takes that as a cue to feed my ass some more anaconda. I don’t know how much she has in there, but it seems to take a long time for a round trip. Tim pushes in more of his cock until I gag, he backs out a tad then begins to fuck my face.

Mary decides, since I have not stopped her yet she should push on, I start feeling something. Has she reached the next sphincter? I don’t know anatomy, but I am feeling something. I’d like to grunt but Tim’s enjoying my mouth. Mary withdraws completely…I feel so empty…feed my ass! She feeds the anaconda in quickly, really starts ramming the first half foot in, then occasionally pushing in more. Shit, I feel my belly getting wet with precum. I start tasting a little precum in my mouth, I look up at Tim, he locks his eyes to mine and smiles, I feel the first blast hit the back of my throat, he proceeds to fill my mouth. Just as I’m about to swallow, Mary slaps my ass and says “NO, don’t swallow!”

She pulls the anaconda out of my ass, Tim helps me stand, and he turns me to her. She reaches up, grabs my face and brings it to her lips, we kiss and she scoops some of the cum out of my mouth. She then breaks the kiss and walks over to Tim and kisses him, passing some cum to him. Well shit, we all swallowed, Tim’s cum. Cat Woman smiles at me and says, “We’re cum family now!” Tim pats me on the back, then gives me a sweet cummy kiss.

I’ve got to hit the bathroom; lube is running down my legs. When I get back Tim has a measuring tape and is measuring to a point where Mary has her finger on the anaconda. Tim looks up at me and says “10 inches Bob! You almost hit my record the first time!” “Oh, joy, swallowing anacondas with your ass is a competition, who knew!”, I said. Tim and Mary both cracked up.

Mary, in her Cat Woman mask looks like she is pouting. What’s wrong Mary? “I just realized you haven’t cum yet.”, she said. Tim says “Well, I’m pretty sure we know how to cure that affliction. We’ll have a contest to see who gives the best blow job. Bob can be the judge.” “Wait, while that sounds fair to me, I happen to know that Mary didn’t have an O either.”, I said. Tim, ever the problem solver said, “Let’s deal with this like adults, in the bed.”



How about this, “Let’s make a sandwich”, I said. “Ok”, they said “but who gets to be the peanut butter & jelly and who will be the bread slices.” Tim said, “How about Mary and I will couple, and you can take me from behind?” Mary, blushed, Tim and I turned to look at her. She was looking at the floor and said in a very quiet voice, “I’ve never had a cock in my ass and pussy at the same time.” She raised her head and locked onto Tim’s eyes. “Are you sure you want to?” Tim asked. “No”, she said, “but if you two go slow, I trust you both not to hurt me.” Tim hugged her and said, “I’ll never let any harm come to you, Baby”. I raised my arms and hugged them both, “You’re safe with me, as I was with you.”

Mary and Tim slipped into bed. Mary turned to me and said “Bob, I think I could stand a Fireball bracer. The bottle is in the kitchen, the shot glasses are in the cabinet above the sink, bring one for each of us, and make them a double, please.” Yes, Mistress, I said and headed to the kitchen.

When I returned, I passed out the shots and sat on the bed. Tim raised his glass a called for a toast. Mary and I raised our glasses and Tim said, “Here’s to cum family, may our friendship and love grow.” Mary said “Yes”, Tim said “Yes”, and I chimed in with “Yes”. We threw back the shots and felt the fire in our mouths and throats followed by the warming in our bellies. I gathered up the glasses and set them down on the nightstand. I turned and Tim was behind Mary, his arms wrapped around her hips.

Mary patted the bed beside her, I slipped into bed and rolled on my side to watch them both. Tim bent down and planted a very passionate kiss on her lips which she returned with equal fire. When they broke the kiss, Mary laid down facing me and she leaned in to kiss me. It sent my head spinning. When we separated, she crawled on top of me, missionary style. I started to protest but she put her hand to my mouth and said, “You are family now, Tim and I discussed it, and this is our way of sealing the bond.” With that, she straddled my legs and laid flat on my chest. Tim, moved around behind her and began running his tongue up and down her slit. This went on for a couple minutes until Tim reached for the syringe filled with lube. He slipped the tip into her anus and pushed the plunger down. Mary said it felt weird. Then Tim helped guide wee willy into her love canal.

Mary slowly backed on to my cock, what a wonderful velvet glove. She clinched her kegel muscles and her pussy tightened around my cock like a wet, warm, soft vice. Rather than thrusting in and out, she clinched me every 30 seconds or so. She would hold it for about 10 seconds then release. She was milking my cock! I’ve only had one other lover that had that kind of control. Fucking awesome.

Tim gave us a few minutes to get acquainted then he pushed a finger into his bride’s voluptuous derriere. When Tim entered Mary the kegels contractions stopped and I began a slow thrusting motion. Mary moaned into my ear, “shit this is feeling pretty good so far”. I kissed her on her forehead. Tim, seeing Mary responding, inserted a second finger. Mary let out a “Ohhhh”, Tim began pumping the fingers in and out. I could feel them caress my dick. Mary started to push back against his hand. Tim add the third finger, Mary froze. I stopped thrusting. I whispered in her ear to just breathe, breathe, try to relax.

She remained motionless for a minute, then I felt her kegels tighten around my dick and Tim’s fingers. She released and said go on. I resumed my slow thrusts and Tim pushed his fingers in deep. Another “Ohhh” from Mary. After a minute or so, Mary says she was ready for Tim’s cock. Tim removed his fingers and lined up his big mushroom head. He asked Mary, “Are you sure, we can stop now, I’ll just finger your ass while Bob fucks you?” “No” Mary said, “I really want to experience this but go slow! If you see me tense up stop.” I raised my hands to either side of her face, I stared straight into her eyes she focused on mine and I said,” Relax & breathe”.



Tim began inserting his cock into Mary’s pert ass. She maintained our eye lock, she open her mouth and emitted a long “ Ohhhhhh! Tim said “My head’s almost in, god, you are so tight! “Breathe baby, relax, let it happen” I said. Tim’s head popped in, Mary breathed a sigh of relief. “Shit, I’m stretched so tight, Stop Tim. Tim stopped, I can feel his head pressing against the base of my cock, man that is going to feel so good when he can begin stroking! It will be like having your cock buried in warm wet pussy and getting a hand job at the same time.

We wait for Mary to relax, I figure the easiest way to take her mind off the stretch is to put a lip lock on her, so I do. She’s hesitant at first but she parts her lips and I run my tongue across her teeth and begin to wrestle her tongue. She engages with me, and I can feel her lust building. Tim feels her ass loosen its death grip on his cock and he slowly pushes it in. I can feel his head slide down the length of my cock until our heads are touching. Mind blown! Mary, is making little mewing noises around our kissing.

Tim begins pulling out, I wait until he is at the base of my cock, then I begin withdrawing as Tim pushes back in. Mary, breaks our kiss and begins a low howling, punctuated with “Yes, more, a little faster”. Mary’s eyes look like a wild animal! I know when our cocks meet, my cock is putting considerable pressure on Mary’s G spot. I hope she will let go and let her orgasm wash over her. Twenty strokes later, Mary goes entirely rigid, her ass and pussy tighten up to the point Tim and I are stopped dead in our tracks. She cums, it is truly a beautiful sight. Her kegel muscles are spasming to the point she milks the cum out of my cock and I think Tim followed suit. We just laid there, exhausted and content. Tim starts to pull out, but Mary stops him, “let it fall out on it own, I want the whole experience.”



Tim laid on her back and began kissing her neck, while I sample her luscious lips one more time. I don’t know who slide out first, probably me, but Tim joined me shortly after. He rolled off his ravaged bride and she put her hands to my face and said,” I hope you enjoyed that as much as I did.” I smiled and said, “Dear, I will take the memory of this afternoon with me to the grave!” She smiled and was about to get up when I pointed out that there will soon be a fair amount of cum, dripping from her pussy and it would be a shame not to share it. Both Mary and Tim laughed. I rolled Mary off me and slid down between her legs and told her to use her wonderful kegel muscles, she pushed and the cum squeezed out into my mouth. It also pushed out of her ass, but I caught that with a towel.

The taste of the mixture of our cum was heavenly, I raised up and Tim leaned in and tongued out a portion from my mouth. He then moved up to Mary and they shared our cum in a very passionate kiss. When they were finished, Mary and I swapped our cum.

Let’s go take a shower! Once in the nice big shower stall, we started washing each other. Special attention was paid to Mary’s perky tits. Tim spent considerable time washing Mary’s pussy & clit and being a gentleman, I spent equal time cleaning all that nasty cum from her ass with my soapy fingers. When Mary had received enough attention, she grabbed us by our dicks and pulled us out of the shower to towel off.

We dressed and headed out to the living room, where I poured another 3 fingers of Fireball into our glasses. Once we were settled, Mary asked me how my experience with the anaconda and spit roasting went. I’ll start by saying “Wow”, I’ve enjoyed being on the other side of a spit roast with Tim and it is fun and with Tim’s deep throating ability amazing. Being on the other side and knowing you were packing the anaconda, I was actually fearful. Would Tim want to drive his cock down my throat? Could my ass really take the anaconda without serious injury? I’ll admit it, I was scared at first. Tim eased my first fear by respecting my limits. He is quite a gentle face fucker! Tim chuckled.

I took a sip of my drink and turned to face Mary. You little girl, with your Cat Woman mask, red peek a boo bra, 12” of anaconda and a wicked smile had my butt quivering in fear. But you eased my fears when we were alone, you said you’d only feed me as much as I could handle, I saw the caring look in your eyes when you said that. So, once I relaxed, it was a very interesting experience. Would I do it again with you two, hell yes! However, I do not wish to attempt to beat Tim’s record. I bow to the anaconda slayer!

I told Mary I was totally amazed at her kegel control. I’ve only been with one other woman who could milk a cock the way you can. She smiled and said, “Why thank you, Sir. Once Tim found out I could squeeze his cock that way, he has encouraged me to continue with the exercises. Your recognition of my ability makes it all worth the effort.” Well, my dear, I’ve already said you and Tim are 1 in a million, guess I going to have to up that rating, 1 in 10 million.

Tim asked Mary “Did the double penetration experience live up to your expectations?” “Just so Bob is aware” Mary said, “Tim and I have experimented with double penetration using Tim’s wonderful equipment and a small dildo. I guess playing like that motivated me to “want” the real thing. It was far superior to our playing around. Both cocks were real flesh and blood. When I would squeeze, I could feel both give a little, the silicone cock doesn’t feel the same. If I could change one thing, and please don’t be offended Bob, I think, I would like to do it with Tim in my pussy and you in my ass. I believe I could have cum faster with Tim’s big ol’ head rubbing against my G Spot while you drill my ass.” “No, offense taken”, I said, “I enjoyed Tim’s “big ol’ head” rubbing up against my cock thru your ass wall.” We all broke out laughing at that one.

What about you Tim? “Well, today I played a supporting role. I enjoyed that because I was able to watch my beautiful wife fuck an ass with the anaconda. I’ve often been on the receiving end, so it was fun to watch her in action. I was so proud of Mary for trying the double penetration. I think you both know I wasn’t 100% on board for that scene. I worried she would get hurt and it would be my fault. I’m just very thankful it worked out and she was able to achieve an orgasm. The fact that she then milked an orgasm out of Bob and me at the same time is just fucking awesome!

There is one thing I hope we can work on. I would love it if Bob can learn to deep throat. I’ll happily volunteer to work with you on that. LOL ! I’d really like to see my cock buried in your throat. “I’m an old dog,” I said,” but I’m up for learning some new tricks, but we might have to practice a lot.”

We shot the shit for a while, then it was time for me to hit the road. We did a group hug and planned on getting back together next weekend. I’ve just been fucked by an anaconda, shared a beautiful woman with her husband and was spit roasted by the two of them. Now, I just want to get home so I can jack off, I got horny just thinking about it.

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