Loading...I’m a well to do 56 year old professional. My home is very nice and nearly paid for. I’m not married anymore, but not by choice. My wife of 32 years, Sherry, was in the wrong place at the wrong time while riding her motorcycle out in the countryside one day. Some kids came hauling-ass out of a grove and pulled right across her path. Thankfully, she died instantly in the accident. I miss her company very much, but I’m not a lonely kind of guy.
See, Sherry and I were both actively bi during our years together, and I’ve been a pretty busy guy of late. It started out about thirty years ago; funny now how it seems like it was just a little while ago…..
In my early twenties I was what you’d call a typical college guy. Decent looking, 6′ 1″, 210, swimmers build. I had done some team swimming in High School which helped the body department, but I wasn’t scholarship material. I was popular enough with the local ladies around school that I could get laid several times a month without too much trouble. Going to college in New Mexico, with its fabulous weather, I was able to land some work cleaning and servicing pools after I finished my morning classes. Yeah, I know, “Pool Cleaner Boy”. Well, in my case it worked out pretty good. Several of my customers were the left-at-home housewives, hubby putting in the hours at “the job” while his lovely lady hung around the poolside. It didn’t take too long before I hooked up with a couple of ’em. Most of these women were pretty good looking, not calendar material, but not too bad. One lady in particular, though, really rocked me…Linda.
Linda was such a hottie! She only stood 5’3″, and had that Sally Field look, you know, tight round little ass, great legs and 36D tits that made your dick ache!! She was in her early forties and had a daughter going to one of the Big 10 colleges back east. I’d been cleaning her pool for a couple months, watching her tanning in the deck chair while I brushed the pool. Those tits of hers straining against that bikini top with every breath she took, would get me so hard… One day she glanced over while I was reaching out with the pool brush and when I stood back up my dick tented my shorts with all its glory. Linda nonchalantly lowered her sunglasses, smiled, and went back to her tan. When I got back to the dorm that night I wacked off big time with that glistening body and smiling face burned into my memory.
The next week, I got to Linda’s house late, about 2 in the afternoon. Usually I was at her place right after lunch. As I walked up the drive, she came out the front door in a sundress and waved me around to the side gate. Damn! I was really gonna miss seeing her out on the deck in that string bikini. I’d been looking forward to this stop all week! I went out back, stripped off my shirt, and went to work. We’d had a good storm the day before and the pool had a heavy layer of silt at the bottom that took a lot of extra work to get up. I was working on the deep end, stretched out with the vacuum pole when an arm snaked around my waist and a very tanned hand got a good hold of my dick through my shorts. Startled, I began to turn around.
Linda said huskily:
“No, you keep working on the pool; let me work on you.”
My cock grew quickly and was rock hard in a matter of seconds. Every time I’d reach out with the pole, she’d stroke mine. With her other hand she began to work my ass cheeks. My sweat from the sun and cleaning the pool had run down my back, soaking my shorts and making my ass cheeks slick. Without losing her grip on my cock, Linda worked her free hand into the crack of my ass and began rimming my hole. Oh, my gawd! I’d never had anyone play with my asshole before! The sensation was intoxicating. After rimming me for a couple minutes, I reached out with the pole, bending way over, and Linda slipped her finger up to the middle knuckle into my ass. Shaking with the sensation of her stroking my cock and pumping my ass with her finger I dropped the pole onto the deck.
Breathing heavily, she whispered:
“You like that Greg? You like me holding you this way?”
“Yes, oh gawd, yes. Don’t stop, please.”
“I’m not going to stop, my dear. In fact, we’re just getting started.”
Linda slid her finger out of my ass and still holding onto my cock, came around and pulled me toward the house. I was delighted to see that my view of her wasn’t inhibited by her bikini. Her naked, tanned body was there in beautiful, full view. The white patch of skin at the top of her ass crack twisted and swayed with each step. As we approached the sliding glass doors I was treated to the reflection of her naked beauty. Her ass patch had a complimentary triple-play in front. Her nipples hard and erect and her pussy was damp with her wetness, a small shiny trail beginning to run down her inner thigh. We made our way inside and back to the bedroom. Stopping at the foot of the bed, Linda slid her free hand back into my shorts, but instead of stopping at my ass, she reached through my legs and snatched my nutsack. With a strength that totally surprised me, she grabbed tight and pulled them back toward my ass, forcing my cock to point straight down. Stepping back slightly she said roughly:
“Drop the shorts, Greg, now!”
The moment was exhilarating!! Here this little woman had me in her control, ordering me to strip naked, and I was loving it! As my shorts hit the floor, Linda pulled back more on my balls, forcing me face first onto the foot of the bed.
“Don’t move! And don’t turn around, either!”
She dropped to her knees behind me and took the head of my cock into her mouth. As I shuddered in a mixture of exquisite pain and pleasure she let my cock slip out of her mouth. Squeezing her free hand tightly around my balls, the nails digging into the soft sack, she cooed menacingly:
“Don’t you come yet, or else!”
She squeezed harder and through clenched teeth I stuttered:
“N-n-no, ma’am, I won’t.”
“That’s my good boy.”
She took the cockhead back into her warm, wet mouth. She swirled her tongue around the hood, licking into the peeslit and then began sliding her mouth up and down the shaft of my cock. Her rhythm began to pick up and my moans of pleasure started to come from deep inside my chest.
Linda let go of my ballsack and began kneading my ass again. Damn! I was really getting heated up! I started swaying into the rhythm of her sucking and squeezing, feeling my hot load building in my balls. My cock began to twitch in Linda’s mouth and my balls started to suck-up when suddenly she let my cock slip out of her mouth and she ordered:
“Stay right there, the fun’s really going to get started now!”
With that Linda stood up and walked across the room to a dresser. I turned my head enough to see that she was glistening with the sweat from our lust. She opened the top drawer and began to sort through it. “Perfect” she said as she pulled something out then turned to face me. Holding behind her back what she had retrieved from the dresser, she grabbed a bottle of oil and slowly advanced across the room to me.
“You really like what you see, don’t you Greg?”
I stared at her naked beauty, unable to break my eyes away.
“You like the way my tits sway and bounce when I walk? The way my juices are matting my pussy hair, running down my leg? It’s making you shiver with lust, isn’t it Greg? You want to lick it all up, don’t you? You’d do anything for me right now, wouldn’t you dear?”
“Yes, anything, anything you want…! I want you so bad!”
“Well Greg, you just do as I tell you, and I promise you’ll get more than you ever dreamed of.”
I nodded slowly, never moving my eyes off her. She disappeared behind me again and dropped back to her knees. She must of have put the oil on her hands because they both began to slide all over my asscheeks. She rubbed up into my crotch and back along the crack of my ass. Her thumb began to rim my asshole and with her other hand she grabbed my cock. Slowly, she began to pump my cock, while she continued rimming me. I was really getting into it now, and my hole began to relax and opened up to her prodding.
“O-o-o-o, that’s good Greg. Just relax and enjoy the way that feels. Yes, that’s it…good boy.”
As I listened to her voice, soothing and sultry, she slipped her thumb into my ass. Slowly, she rotated her thumb while pushing against the inner muscle, resistant to her probing.
“Relax, baby, let momma make you feel all good inside.”
My eyes were shut, my inner vision seeing her behind me, stroking my cock and sliding her thumb into my hole. I relaxed more, and it slipped in until her hand was buried in the crack of my ass.
“U-n-n-gh!! Oh yeah, oh yeah. Oh, that feels so…so…good…”
She began to pump her thumb into me in time with her jacking my cock. My gawd! I was losing myself with the sensations she was giving me. I could hardly believe what was happening!! This was more than I had ever imagined! It felt so fucking goooood!!! My cock was aching with the build up! I could feel that I was getting ready to unload. My cock started to swell even bigger with the heat of our passion! This was it! My back started to tense as the cum boiled in my sack…and she stopped! She slowly pulled her hand away from ass, a sucking sound coming from my hole as her thumb slid out. She released my cock and began to stand up.
“You’re ready now, baby. Momma’s gonna give you what you really need now.”
I turned my head and saw what she had gotten from the dresser. It was a double-dildo and harness!! The cocks were each about 8 inches long.
When she saw the wide-eyed look on my face, she cooed:
“Don’t worry baby, I’ll be real good to you, I promise.”
I couldn’t take my eyes off her as she tauntingly slid one of the cocks into her dripping wet pussy. Her eyes kinda glazed as it slid up into her hot, wet hole. She began to run it in and out of her, covering it with her honey. Then, with a look of mischievous glee, she turned it around and shoved the other end into her. With it buried in her pussy, she picked up the harness that was lying on the floor next to her feet. Stepping into the open loop, she pulled the patch over the dong, and secured the strap around her waist. The sight was unbelievable!!! This tanned, gorgeous woman was standing there with a wet, hard cock in her hand, and it was hers!!!
Linda stepped up behind me, holding that cock and smiling enticingly.
“You’re gonna love this, baby. Momma’s gonna do you like you’d never imagined.”
With one hand she spread open my asscheeks and with the other guided the cock toward my hole. My ass clenched as the cockhead touched my hole. I yelped when Linda unexpectedly smacked my ass hard, heat building in the spot where she had hit it.
“Don’t! You’re going to take it from me, the way I want to give it to you.”
Again she pressed the cockhead against me. Closing my eyes, I willed myself to relax. Linda pushed, my virgin ass reluctant to give up its cherry. She began to slowly rock into me, the head slipping passed the first ring muscle.
“O-o-o-oh yeah, let me in, baby, let momma show you how good it really feels.”
She presses in and comes up against my inner ring. My ass refuses to open up for her and she slaps my asscheek hard! My ass tunnel flexes around the didlo’s head and as it relaxes from the slap, Linda pushes forward against it, forcing it to open, just a little.
“That’s it baby, relax. You’re gonna love this.”
She slaps my ass again and again my ass flexes around the invading, silicone cock. As the inner ring relaxes again, the pressure Linda has against it allows her cock to open me up a little more. Again she starts to rock against me and I fall into her rhythm. My ass relaxes and she slips into me, my ass finally giving in to her incessant invasion. The incredible heat of her passing into the virgin territory of my ass slowly fades as Linda continues her rhythm, driving into me with each thrust until her thighs are tight against my asscheeks!!
My mind is reeling as I lose myself in the pleasure of her cock filling me. Linda slowly begins fucking my ass, grabbing onto my hips and sliding her cock out nearly to the tip before driving back deep into my ass. Her rhythm begins to pick up as my ass welcomes her into me. She’s really starting to drill me now! The feeling is just so incredible!! I never believed it could feel this good!! We’re both getting into it now, beginning to get into a lusty, panting, driving rhythm. My orgasm is mounting steadily. Linda is pounding my ass now with her cock, sweat beginning to drip off her chin and onto my back.
Suddenly, quietly, over the lusty noise of our passion, I hear a man’s voice:
“So, what do we have going on here?”
I snap my head around to see Linda’s husband Dan leaning against the doorway to the bedroom, his hard-on obvious in the crotch of his pants. Without breaking her rhythm of fucking my ass, Linda pantingly replies:
“Finally breaking in the poolboy, darling. Isn’t he luscious? He’s such a good boy, aren’t you Greg?”
She continued pounding into me. The passion continuing to rise in me as I look into Dan’s face and harshly whisper:
“Yes, ma’am.”
“Why don’t you come join us, dear. I’m sure Greg won’t mind. In fact, I’ll bet you can really open him up to how good this can be.”
With that, a smile breaks across Dan’s face, and without taking his gaze off us, peels off his shirt and kicks off his shoes. He’s in pretty decent shape, with smooth abs and nicely buffed chest. Dark hair covers him, his skin easily visible beneath it. It circles his nipples and runs down across his stomach, disappearing into the top of his pants. I’m locked into his gaze as he starts to play with a nipple, pinching and tugging until it gets hard and points longingly from his chest.
As Dan unbuckles his belt and tugs down his pants and shorts, I see the trace of dark hair pointing to his groin still hidden from me. I suddenly realize that I’m licking my lips, staring at his crotch as he lowers his clothes. I want to see him, I’ve got to see him!!
Dan sees the lust in my face and pauses his movement, bringing a quiet whimper from me. Again, he pushes downward until the head of his rock hard cock comes into view. I lick my lips again as he completely uncovers his pulsating member. I’m mesmerized as he kicks off pants and begins walking toward the bed. With Linda continuing her driving, pounding fucking of my ass Dan climbs onto the bed and crouches in front of me, his cock inches from my face. I see a pearly drop of pre-cum slowly seep from his pee-slit and I find myself yearning for it to drop into me.
“He looks like he really likes what he sees, darling. Don’t be such a tease, baby, let him have a taste.”
Dan slides forward on the bed, his legs spread-eagle on either side of my head. Just as Dan’s cock touches my lips Linda gives my ass a big thrust and my forward lunge causes Dan’s cock to slide halfway into my hot, wet, hungry mouth! The sensation is beyond anything I’d ever expected. The contrast between the softness of his cockskin and the hardness of his cock itself is amazing. I start to suck hungrily at Dan’s hot, hard rod. This feeling is more amazing than I could’ve imagined.
As Linda continues to pound my ass, my lunges cause my mouth to slide up and down Dan’s cock. Dan begins to moan as my sucking mouth draws him into me. He starts a rhythm of his own and begins to fuck my mouth. Now I have them both drilling into me, filling me with cock from both ends. Dan’s cock, nearly as large as the dildo Linda’s fucking me with, begins to bang the back of my throat, causing a gagging motion. Dan eases back a little and I begin to adjust to the invasion of my face. I’m starting to go over the top now, sucking harder on Dan’s awesome tool as Linda continues filling my ass.
We’re all breathing heavily as we approach orgasm. Linda begins to shudder first as she hits her peak, quick little thrusts now as she keeps the dildo buried deep into me. My own load starts boiling up as the sensations of this double-fuck courses through me. Just as my cock begins to spew its pent-up passion, Dan grabs the back of my head and spurts his salty cream down my throat! I continue to suck him hard, milking every stream, every drop from his cock. Linda collapses onto my back as her orgasm subsides and Dan falls back onto the bed, his cock slipping out of my mouth with a distinctive slurping pop.
I’m completely wiped, laying there, half on, half off the end of the bed, Linda’s heaving tits pressed tightly into my back, Dan’s limping cock draped across his thigh. Eventually, Linda pulls out of my ass and strolls into the bathroom. I roll over and slide down to the floor, still exhausted from this lusty assault.
As the shower comes on, Dan slides down to the end of the bed and drapes his legs over my shoulders. I turn my head and am greeted by his hardening cock just inches from my face. Grinning down at me, he gently grabs my hair and pulls my mouth back onto his cock. This time, I open up willingly and glide my mouth down onto his hardening shaft until my nose is buried in his pubic hair, the head of his cock turning down into my throat. I quickly suck him back to his full, rigid glory. With Linda in her shower, I back off Dan’s cock and climb onto the bed with him. Lying on my back, I spread my legs, grabbing them behind the knees and lift my ass invitingly to Dan. His smile grows bigger as he climbs on top me and easily slides into my hot, hungry ass. This is really what I want, Dan’s hard, hot, throbbing rod pumping in and out of my ass.
I quickly get into a rhythm with his thrusts and lose myself in the incredible sensations of this man fucking my ass. As the shower stops and Linda steps into the bedroom our eyes lock as she watches Dan taking her place in me. She smiles slyly as Dan suddenly pumps into me hard and fast before he grabs both my asscheeks and thrusts deep into me. I can feel his cock spasm and twitch as his load shoots into the depths of my ass. With one final thrust, he falls onto me, his chest heaving into mine.
Later, after Dan and I cleaned up, we all laid out by the pool in the cooling evening air and talked about the afternoon’s festivities. Linda and Dan said how much they enjoyed having me there, happy that I wanted to come back again for some more fun.
That was the beginning of a very enriching school year. The times that Linda, Dan and I had were very exciting and fulfilling. I have never regretted any of it, and am actually very thankful that they “opened me up” to the pleasures of the bi world. What was really extraordinary though was when their daughter came home for summer break. She turned out to be a very remarkable woman. She showed me the true meaning of ‘keeping it in the family’. We enjoyed each other so much that by the end of that summer, I asked her to marry me, so we could be a family forever. Yep, Linda, Dan, myself and Sherry would have some grand and glorious times together. Maybe I’ll tell you about them sometime……