Due Diligence Ch. 01

"I've started dropping hints about you to her," Jack told me, "but we've still got some work to do. Can you come by for a bit tonight?"

"Tonight?!" I replied, surprised. "You mean, she's..."

"No, she's away for a couple of days, Randy, but there's some more... evaluating, let's say." Even over the phone, I could hear the smile in Jack's voice. He was enjoying this, and at this point I wasn't sure which of us was more excited. Not that it mattered.

I agreed to come by; Jack had advised me to keep my schedule clear, so it wasn't a complete surprise, and as... unorthodox as this all was, he seemed a decent enough sort and I was enjoying this.

Jack had approached me the week before. He'd seen my profile on AFF and presented me with a tantalizing offer; he wanted to provide an unforgettable surprise for his wife, and he'd asked me to meet him for a drink to discuss it. I asked him about the wife, and he refused to give any details. "Not until I know for sure we're going ahead with this, but I can promise you'll be impressed."

Yes, I was flattered. Newly single at 42 (by amicable, mutual agreement), I'd been out of the scene for over a decade during my marriage. In the six months I'd been on my own (with half-time custody of our 9 year old boy), I had decided to "work on me" before going after anything. Went for a little counseling, hit the gym, and I was definitely starting to feel ready for a little fun. I'd dropped my spare tire and leaned myself down to 240 on my 6'4" frame with the help of P90X and workouts at a local MMA academy. I'd never be climbing in a ring, but my coordination was improving along with my muscle tone, and I was gaining some badly-needed confidence. I'd posted my AFF profile a few weeks before with a few, tasteful, discreet pics (and one decidely UNtasteful one; I didn't want my casual intentions to be mistaken). I'd chatted with a few women back and forth, but I hadn't found a situation I was completely comfortable with, and I wasn't desperate enough to jump.

Jack and I met for the first time at a sports bar on a quiet night. He was definitely a different physical type, maybe 5'6" and compact. He struck me as one of those wiry little fucks that would be easy to underestimate in a fight. Older than me, I figured him to be early-to-mid fifties, but active. I had a feeling he ran.

I introduced myself and he laughed "Really? Randy?" I smiled in response, "Yessir, really Randy. Take that any way you want."

We got a beer and found a quiet table. "First thing I want to make clear, Randy: I'm not gay, not bi. I'm not after your dick. This is all for my wife."

"Thanks," I said, "Won't deny the thought crossed my mind. This is a little, um, unusual."

Jack explained: he and his wife (who he still wouldn't name or describe aside from "athletic with a few curves") had been married close to 30 years, and while their kids had been growing up they'd both played it completely straight. A strong marriage, never a hint of infidelity. "Not that we NEVER fought," Jack laughed, "but I always felt VERY lucky."

Once the last of their three kids flew the nest, they traded their suburban home for a nice condo. Jack had a successful business, "wifey" had a successful corporate career, and once they were on their own they started indulging each other, tentatively looking for adventure, but together.

"So you're getting into swinging?" I asked.

"A little," Jack said, "but we're being careful. My wife arranged a... surprise for me a little while ago," the recollection made his eyes twinkle sharply, "and she went to a lot of effort. 'Due diligence', you might say."

I agreed with what he was saying. I hadn't been in "The Lifestyle", but I'd thought about it a lot, and read up as much as I could. I could understand it being a minefield, especially for a couple that valued discretion. I was flattered he'd even consider me for this.

After bullshitting about women and work for a while, I looked Jack in the eye, "You sure your wife will be into this?"

"Oh, you're her type, for sure. She's turned on by bigger guys, especially since I'm all she's had, pretty much ever. I just hope you understand, that 'due diligence' I was talking about is going to take more than a couple of beers."

"What do you need?" I asked, a little offended, "A fucking background check?"

Jack held his hands up, "No, not like that. Let's just say there are some pitfalls I want to avoid, and I hope you understand. Trust me, and let me evaluate you a bit. Nothing bad, don't worry. Like I say, trust me. If we do this right I promise you won't regret it. There's a couple of things I want to check out with you, and I'm gonna say it will take maybe a week. But it will be worth it for all of us. Really."

We shook hands, and agreed to meet at the YMCA for a workout the next night ("I want to see how much it takes to wind you," Jack said with a smile). He wasn't kidding, either. We ran a couple of miles on the track and did an interval training session, then a quick round of weights. He was in pretty decent shape, but I was stronger. I was grateful for the fight training, it definitely helped my wind. Jack discreetly checked me out in the locker room, of course. It's hard to be sure in the showers, but I was pretty confident that I was somewhat better-equipped. And I understood that Jack needed a little more confirmation that those AFF profile pics were really me.

As we left the Y, he said, "Okay, this is looking good so far. Bear in mind you're not the only guy I've ever checked this out with, but I'm comfortable with what I see. There's a couple more things I want to, um, 'evaluate'. Keep the next couple of nights clear, okay."

"Sure, Jack," I replied, shaking his hand. I respected the effort he was going to in making sure his wife's "surprise" would be a good one. Jack had explained that some of the younger guys he'd considered came across as inconsiderate and cocky (which was why he was looking at me, a guy only a few years younger than his wife), and a couple of others just seemed... off-kilter. Nothing specific, but kind of sleazy. Jack wasn't picking that vibe up from me, so he hoped I could be a little more patient.

So, two nights later he asked me over for a little more "evaluation", and I was still good with what he was doing, but when I got to his condo and he led me straight to the Master Bedroom, I cocked an eyebrow at him.

"I told you, Randy, I'm not after your dick. I've got a few puzzle pieces to fill in for you, though, and I'm going to push your comfort zone. You'll see why."

I sat on the bed as Jack brought out an album of Polaroids. "Yes, these are recent", Jack said, "she's not comfortable with digital photos, not even with me, and I don't push shit with her. Randy, meet my wife, Leah."

Leah looked to be 35. "How recent are these?" I asked Jack. This week," he replied, "yes, she's 48. Yes, she looks that good. I told you, I'm a lucky guy."

The first few shots were completely innocent. Leah was wearing a nice, short black cocktail dress, set to go out. GREAT legs that had just a hint of muscular definition to them. Mid length, dirty-blonde hair and green eyes. A pretty, professional smile, but in one shot she had her mouth wide open, her tongue looking ready to lick the precum off an off-camera cock.

"Oh yeah?" I said to Jack, smiling. He smiled back as he turned the page, "Just wait."

There were only a few shots on the next page, but they were as hardcore as you could hope. In one shot, she was holding a dick (presumably Jack's) between beautiful c-cup tits with VERY firm nipples. In another, she was getting fucked anally. "I'm biased", Jack said, "but she's got the most incredible ass I've ever seen"--I couldn't argue from what I could see in the pic. The last pic was a creampie shot, of just her pussy. Trimmed, but not shaved, with thick lips that she held apart with french-nailed fingers.

"Okay," I agreed, "she's hot, and she's hot to trot... and she's looking forward to this?"

"You have no idea," Jack said, "I took these the other night when I told her I might have found someone she'd be comfortable with. Trust me, she wanted to show off for you."

I was hard enough to make it uncomfortable to keep sitting. I stood, with a prominent bulge. Jack laughed, "So, that worked for you, huh? Go stand over by the closet. And put this on..."

He'd handed me a blindfold. "Here's that bit about pushing your comfort zone, Randy. I need to make sure nerves won't be an issue for you. Put it on, don't worry."

Jack had stood up on the far side of the bed. I shot him a doubtful look, but put on the blindfold like he'd asked and stood still. In a few moments, I could sense someone standing in front of me. "Hi Randy," a pleasant female voice said, "I'm Sheila."

"Ever fuck a woman you can't even see?" Jack asked slyly. "Sheila's wonderful, trust me. She's the 'surprise' that Leah set up for me and she's agreed to help me test you out. Call this your final exam."

"Oh, Jack," I said as I felt Sheila start to unbutton my shirt, kissing her way down, "I didn't expect this... I didn't bring anything..."

"No worries," he said, "I'm figuring you for Magnums?"

I laughed out loud. "Sheila, you sure you're good with this?" She was rubbing my hardon through my jeans now, so I was pretty sure of what she'd say.

"Ohhh baby!" she said, "you don't know how many fantasy buttons this pushes with me!"

She was still standing, pulling my now-unbuttoned shirt apart so she could nibble and suck my nipples. I threw my head back with a gasp, almost losing balance.

"Randy, baby! Don't fall down!" Sheila said as she turned me around and guided me to lie back on the bed.

Jack said, "I'm going to watch, if you don't mind. Ever had to perform for an audience, Randy?"

I thought back, "Um, no... not that I ever knew, anyway..." Sheila was on top of me now, straddling me. She'd been naked when she came in the room, and I could smell her arousal already. She was nuzzling my neck and kissing my ear, slowly rubbing her pussy up and down on the bulge in my jeans, which was getting steadily more uncomfortable and her tits pressed against my bare chest. I reached down with both hands and gripped her ass. She was a little padded, but not unpleasantly so, which didn't do anything to lessen my own arousal.

"Ohhhh, Sheila..." I groaned, "I'm getting a little uncomfortable. Can you help?"

I heard her chuckle. "Maybe you shouldn't wear such tight jeans, you bad boy." She climbed off me. My feet were on the floor, and I could sense her getting on her knees between my legs as she unbuttoned and unzipped my jeans. She didn't pull them straight off, but pulled my thick, straining cock free. She stroked it a few times, almost lovingly, before I felt Sheila take me in her mouth. "Mmmmmmm," I heard her moan before she released me to say to Jack, "Leah is gonna owe you BIG TIME!"

"Good," Jack said with a hearty chuckle, "It's about time!" I loved the flattery, and Shiela's mouth felt wonderful. I definitely didn't feel self-conscious, even with Jack watching. If anything, having an audience was turning me on even more. She finally pulled my jeans down to my feet so that she could spread my knees and stroke my balls while she sucked my cock.

"Mmmm, Randy," Sheila cooed, "has anyone ever told you you've got a BEAUTIFUL dick?"

"I'm glad you like it," I replied cheerfully.

"How big are you? Is that nine inches?!"

I honestly wasn't sure. "I don't think I'm THAT big... It's not too big, is it?"

"Ohhh, honey, there's only one way to find out."

I heard Jack say "here you go" as he handed Sheila the condom. She gave me a few more strong strokes before she rolled the Magnum down my shaft, then she had me shift back further on the bed so she could climb up and fuck me. I could feel her hovering over me, stroking the head of my cock up and down her lips as she bent over and stuffed a nipple in my mouth. I loved it; she felt great, and smelled wonderful. It was almost better having the blindfold on; like I was less distracted. I had my hands behind the tops of her thighs now, pulling her lips apart as she used my protected cock to frig her clit. It made her catch her breath every time her clit ground against my cockhead, and I thought I keep going like that with her all night. The wet noises of my cockhead rubbing up and down her cunt were getting louder with every stroke, until she finally put me inside and began to slowly sink down.

"Oh-oh-ohhh..." Sheila moaned. She was able to work about two-thirds down on that first stroke, then rose up again until just my dickhead was inside her. "Okay, it's official," she said, breathing heavy, "that's the thickest cock I've ever tried to stuff up my poor old puss."

She slowly pushed down again, this time taking all of me. It took her some work, and when I was in all the way she collapsed down to my chest and kissed me again. "Ohhh DADDY that feels good!" Sheila propped herself back upright again, and began to work her hips up and down, sliding me even deeper in.

MY turn to moan, now, as her rhythm picked up. She was getting so wet that I could feel it seeping down to my balls, and the sensation was making me crazy. I grabbed Sheila's ass with an iron grip--digging my fingers into her cheeks--and began to drive myself upwards into her as hard as I could. My strength overwhelmed her, and instead of her fucking me from on top, I was pounding her cunt hard from underneath. I could hear her stifled moans with each stroke, "Mnnn-Mnn-MMMMnnnn!", like she was biting her lip.

She suddenly pushed the blindfold over my forehead. "Waa-waatch me-meeee cummm-mmm," she tried to say as I kept fucking her from down under. She was sweating, with thick, wavy brunette hair now flying everywhere. The areoles on her bouncing tits were wrinkled and hard.

With a few more of my deep strokes Sheila was arching her back, wailing like a wolf-bitch in heat, her juices flooding my ball-sack. I was close, but not done yet. I'd landed on the bed crossways, and now Jack came around the foot of the bed, his pants down and his cock looking like it would burst. As Sheila finally settled down (with several shudders that made her cunt spasm around me and almost send me over the edge), she turned, smiling, and began to stroke Jack, then leaned over to take him in her mouth while I was still slowly sliding in and out of her snatch.

I'd seen lots (and LOTS) of porn, but I'd never actually seen sex right in front of me like that, and I kept fucking Sheila slowly while she sucked Jack off. I'd never even seen another guy hard in the same room as me before; Jack was smaller than me, sure, and he didn't taper to a thicker base like my cock did. Jack's dick was straight, with a huge, dark purple mushroom head. He was ready to blow, and he let out a long, loud "Aaahhhhhh!" as Sheila took his full length down her throat, inches away from my face. She buried her face until her nose was in Jack's thick pubic hair. He took her head and fucked her mouth for a few strokes, until he released her with a groan, shooting all over Shelia's face and tits as she jerked him off, yes, even with the odd glob landing on me.

Seeing that, and smelling the musky-acrid scent of Jack's semen started the approach of my final cum. I easily flipped Sheila on to her back and her eyes fluttered upwards as I fucked her as hard and deep as I could remember ever fucking my ex. I slowed for a few strokes, looking down to watch myself sliding in and out, pushing her pink cuntlips wide apart as my thick base pushed all the way in.

But in a couple more strokes I was on the edge of control, and tipping over. I had Sheila's legs pushed wide, going deep-deep-deeeeeep, but as she could feel my tension rising she cried, "No! I want to see you!"

I pulled out and slipped the soaking condom off, and Sheila grabbed me with both hands to finish me off, the first shot spurting far, leaving a trail up her face, into her hair, and on to the bed behind her. I'd never had a woman do that to me. I felt like I'd come for an hour, the cum shooting out to cover her tits, her neck, even her face. I must have shot ten, fifteen times before I finally felt my almost-painful orgasm pass, the last of my semen dribbling in to Sheila's belly-button.

Jack had pulled his pants back up by then, and he had a grin a mile wide. Sheila smiled at him, then playfully grabbed my softening dick. "No! Leah can't have it! I want to keep it!" We all laughed, then Jack said "she shared mine with you... maybe you can make a deal..."

She looked back up at me. "Don't mind us," she said, "we're kind of, uh, different as friends go. We have fun."

"I can tell," I said with a smile, "We'll see how it all works out."

Jack chimed in, "Performance anxiety isn't an issue for you, clearly. Looks like my Leah's in for a treat!"

Sheila went to the bathroom, and Jack lowered his voice. "There's one more base I'd like to cover. Think about it for a bit, okay?"

I shrugged, "What?"

"How soon can you get in to your doctor? And get tested?"

"I've BEEN tested. And I'm clean," I said.

"If I told you Leah's clean, you'd believe me, right? Would you take me to your doctor and have him tell me you're the same? She got fixed after our last kid, that's not a problem."

I looked at Jack. He was actually ready to let me fuck his wife bareback if he could trust I was clean. And, yes, I believed him about Leah.

I smiled back at him, "I don't have to think about it. I'll line it up and let you know."

Jack's face lit up. "She's gonna be fucking AMAZED!!"