Condo Lockdown Pt. 01

The first time Phoebe and I tried anal, we'd been drinking and fucking all afternoon. We were taking a break, both relaxed but still slightly horny, when she started a video of a MILF getting her ass fucked by her daughter's boyfriend. She'd caught him lying naked in her daughter's bed while her daughter was taking a shower.

Phoebe started talking to me like she was the MILF and I was some teenaged kid and the next thing I knew I was eating her ass, mimicking the action on the screen. When the MILF found a dildo under her daughter's pillow and handed it to the kid saying, "Loosen up my ass with this," Phoebe handed me a medium sized dildo and a bottle of lube. She hissed and groaned as I worked the small toy into her.

She later admitted that she'd only ever used her smallest dildos and the modestly sized butt plugs she owned on her ass before that. She'd frozen up when she tried any larger toys.

From there Phoebe had me work up to an average sized dildo, and then she took my cock. I'd had anal sex before, but Phoebe was my first anal virgin. I was nervous about hurting her and turning her off anal, so I tried to be as slow and gentle as I could. When I bottomed out in her ass, she let out a sound that said she was happy about her achievement, but at the same time felt anticlimactic.

We had a slow, leisurely fuck up until the end when she asked me to pound her hard. She was able to cum with a little manual help and afterwards proclaimed that we'd be doing that again.

She later told me that other women had said they could never take more than a few inches of their lovers' cocks in their asses while she had felt like she could have taken a much larger cock. I kidded her about being a size queen already and she just said, "More for the spank bank." Later still, she told me she'd bought the purple and white dildo specifically for her size queen fantasies.

Phoebe admitted she'd done a lot of research on anal sex. She'd learned that working up to it slowly, being relaxed and taking your time were essential for first timers.

She'd planned to have me fuck her ass that day, so it was no coincidence she had lube and appropriately sized dildos handy. She knew sex was a great way to relax, so she made sure we were both blissed out and happy before she started the anal video. She also knew we wouldn't be in a hurry after we'd already cum a couple of times. She picked that video to use as the pattern for our first attempt at anal specifically because it had a slow buildup.

Now that it was my turn to take it in the ass, Phoebe decided to relax me by giving me a slow, sensuous blowjob. She knows that I love to watch her suck my cock, and she loves to put on a show.

Her closet doors are mirrored, so I could look down at her face and watch my cock disappearing into her talented mouth, or I could look in the mirror and see her body in profile as she worked my shaft. She'd learned to put on a show for the mirror, undulating her body so it looked like she was performing an erotic dance while she sucked me. I was always enchanted by her tits hanging down and the sinuous motion of her ass. In those moments she looked more like a twenty-something hottie than a fifty-something cougar.

She took her time making love to my cock, bringing me to the edge and letting me slip back several times before she sucked me to one of those toe-curling climaxes that seems to last forever. It started gently and then built in waves until the first volley of hot sperm burst from my cock. I felt my balls contract in one hard, slow pulse after another, and I felt Phoebe swallow each spurt as it hit her tongue. Just when my cock was becoming too sensitive, she pulled off, moving to delicately lick and suck my twitching balls. When a final drop leaked out, she licked it up and then slid up to lay on me as we had a slow make out session.

When I caught my breath, she slid back down my body and started licking my balls again while she pushed my legs apart and up. Realizing what she was trying to do, I grabbed my knees and pulled them up, spreading my ass for her. I gave a little gasp as her tongue touched my pucker. She'd rimmed me before, but this seemed more momentous.

She smiled and continued to lick me, gradually becoming more aggressive. Soon she was lashing my asshole with her tongue, sucking it and probing it as deeply as her tongue would reach. I was desperate to open my ass for her and urge her to lick all of it at once. I couldn't help but groan when she tickled the inside of my ring with her tongue.

Then she was sliding a lubed finger into my ass. She knew about prostate stimulation, but neither one of us had done it before, so she stroked and probed my hole until my cock jumped and I said, "Right there!"

She stroked a few more times, marking the spot, then added a second finger and resumed her slow finger fuck. My ass accepted her small digits without any discomfort, and I was really liking what she was doing. Just as I was debating whether she could make me cum just by finger fucking my ass, she switched to the small dildo.

Although it wasn't any bigger than her two fingers, psychologically it was a big change and I tensed up. My cock had been hard, but it started to soften immediately. Phoebe took it into her mouth and sucked until I was focused on the feelings in my cock. Then my ass relaxed, and I had two inches of dildo in my rectum before I knew it.

Phoebe was fucking my ass with short strokes, not really trying to push in any farther as she said, "That's what you wanted. You wanted to feel a cock in your ass. Your dick tells me you like it. Your hard cock twitches every time I give you an inch." Then she asked, "How about another inch now?" as she pushed the dildo further into my ass. Advancing just a bit at time like that, she worked all five inches of the little dildo into my ass in seemingly no time. Once it was in to the base, she added some lube and gave me a gentle fucking, angling to hit my prostate again.

When she was pumping a steady stream of precum with every stroke, she left the dildo buried in my ass as she lubed up the average sized dildo. While I was waiting, I angled my ass towards the mirror so I could get a look at the pink, flared base flush against my ass. For some reason that looked hot to me, and I had Phoebe take a picture.

She pulled the small dildo out and immediately began a slow, steady insertion of the larger one. I could feel my ass stretching, but it was still a pleasant fullness with no real pain. She took several full-length strokes before pulling the dildo out and adding lube. As she fucked my ass at a moderate pace, she said, "Do you want me to keep fucking you?"

I said, "Yes. Fuck me. I want you to fuck me."

She picked up her pace and said, "And now?"

I could feel each stroke hitting my hotspot and I was more certain that I could cum from an ass fucking, so I said, "Yes, fuck me harder."

She kept picking up her pace and I was urging her to go harder, until she was jackhammering my ass and I was flushed and breathing hard. Then my ass was empty, and she said, "You need this now," as she lubed up the seven-and-a-half-inch dildo.

I could feel cool air in my asshole, then Phoebe fucked me with three well lubed fingers. As soon as her fingers were gone, I felt incredible pressure against my ring. Phoebe said, "Push out and let it in," as she applied steady pressure.

There was a burning stretch in my sphincter. I let out a whining groan, blowing out short, panting breaths in an effort to relax while she applied firm pressure. Then I felt the head push through, and the burn turned to a dull ache as I switched to long, slow breaths. I winced a little as she pushed the head through my inner sphincter, but then I almost didn't realize she was just continuing to slowly and steadily press the full length of the fake cock into my ass. It came as a bit of a surprise when I felt its balls against my taint and she said, "Is that enough cock for you?"

I was still turned towards the mirror. Looking into it, I could see those big fake balls between my ass cheeks, and I had a peek at my stretched ring. Phoebe gave me a couple of short strokes while I watched, then took another picture without me having to ask.

She started long dicking me with the dildo, pulling it out until the head was pulling against my ring and then ramming it back in. She was getting a kick out of the way I grunted every time she slammed her cock into me. My cock was hard and leaking, and she stroked it with one hand as she fucked the dildo into my ass with the other.

When my cock was throbbing on the edge of cumming, she changed to short, fast strokes She was somehow able to suck and jack my cock while continuing to fuck me hard with the dildo. When she took a break from sucking my cock, I was amazed to see how much precum she was milking from me.

I was thrilled to feel the head of the dildo almost constantly pummeling my prostate, sending out waves of pleasure that radiated from there to my clenching ass, my throbbing balls and up to my dripping cock head. I could feel a big orgasm building from that spot. It was unlike any orgasm I'd ever felt before and I found myself grunting and moaning as I thrust my ass back against her pounding strokes.

By the time I came, my knees were tight against my shoulders and my ass was completely off the bed. Phoebe rode with me, never stopping her assault on my ass and my cock. I stayed there, quivering and contorted, through four tidal waves of orgasmic power before my abs finally unclenched.

Phoebe took my first blasts in her mouth, and when the first wave passed and I was lying there enjoying the aftershocks, she leaned up and shared my cum with me in a sticky kiss. She didn't stop pumping her toy into my ass, and my cock continued to spew, untouched, with each stroke of the dildo. I sprayed hot sperm over both of us as we shared the cum kiss and then continued to ravage each other's mouths.

When my cock stopped spitting, Phoebe held the dildo in my ass as I dropped my feet to the bed. My ass ring was rhythmically tightening around the shaft and Phoebe moved the dildo gently in time with the spasms. She waited until my ass relaxed completely before she pulled it out, leaving me to feel a disappointing void.

As we lay there in each other's arms she said, "So, I guess I should order that harness now."

When the harness arrived, I found out that wasn't all she'd ordered. She'd small, wearable butt plugs for each of us, and for me she bought a butt plug the same diameter as her large dildo and an app controlled vibrating butt plug. I think the last one was actually a present for her, because she made me wear it for a game night while she controlled it from her phone. I discovered that you'll probably never cum from a vibrating butt plug, but it can be damned distracting anyway.

Not long after that, we were having dinner together when Phoebe said, "I hooked up with Natalie yesterday."

I just raised my eyebrows and looked at her, waiting for the rest of the story that I knew she was dying to tell. She didn't disappoint.

"She came by for her regular workout, but she was dressed differently. She usually wears a sports bra and calf length yoga pants. This time she was braless, wearing a tank top that showed a lot of side boob and cleavage, and she had on a tiny pair of running shorts. She usually works out with her hair in a tight ponytail, but this time she had it in a loose headband."

"She decided to run on the treadmill. As I told you before, we usually workout together, so I joined her, running on the elliptical."

In Phoebe's workout room, her Peloton is right inside the door along the left wall, her elliptical is on the far wall, and the treadmill is against the wall to the right. The treadmill and elliptical face the same corner where she has a small TV screen set up. That makes it easy for someone on the treadmill to converse with the person on the elliptical, or they can both watch TV while they workout.

Phoebe continued, "Her C-cups were moving pretty good as she ran, and I'm certain she was adding some extra bounce to her step. With the way her top was cut, I got to see pretty much all of her tits. We didn't converse much because she's gotten to where she can go hard for a long run, but she did make some flirty remarks."

"When we finished our workout, her top was drenched with sweat. She looked like a competitor in a wet T-shirt contest with her shirt plastered to her tits and her nipples clearly showing through. That's when she asked me, 'Are you going to shower now?' I of course said yes, and she said, 'Great. I hope it's okay if I join you.'"

"It wasn't a question, and she didn't wait for me to respond. She just walked to the bathroom, stripping as she went. She made herself at home adjusting the shower and then got in, leaving the door open for me."

As I said, our condos are supposed to be luxury units. One of the things that lets them make that claim is the bathroom fixtures. Each unit has a walk-in shower big enough for three people, a soaker tub, and a bidet. The showers have four heads, each with individual digital controls. Each unit also has its own tankless water heater, which means an endless supply of hot water. I've personally taken a forty-five-minute shower that was almost as good as having sex.

Phoebe went on, "As I stepped into the shower, Natalie was soaping up my sponge. She led me under the water, and when I was wet, she spent ten minutes washing me from head to toe. She didn't do anything sexual, but it was the most sensuous shower I'd ever taken. She worked the knots out of my shoulders and massaged my hands as she washed them. She knelt in front of me to wash my legs and feet, lifting them onto her bent knee and giving them a little massage as she sponged them clean. She had an amazingly teasing touch as she washed my tits and ass. She only spent a few seconds washing my pussy, but it triggered a rush of wetness. I was utterly relaxed and utterly horny by the time she was done."

"She had me kneel down after that so she could wash and condition my hair. It was incredibly sensuous feeling her hands running through my hair, and she gave me an incredible scalp massage in the process."

Natalie is a cute little blonde, just over five feet tall with a round face and big blue eyes. She'd had a little belly and some saddle bags that made her look older before she started her workout routine, but since then she'd developed a toned, but still curvy figure. The only thing that gave away her true age was the laugh lines around her eyes and a few gray hairs that you could just pick out in her golden blonde hair.

Phoebe had been a volleyball player in college and still looked like she could step on the court and play for her old team. She's just short of five foot ten with an athletic build that's intimidating to some men. She told me once that she thought her tits looked small on her, but her firm B-cups perfectly complement her svelte, athletic look.

Her hair is pure white, thick and straight, hanging down to the middle of her back and making a striking contrast to the golden complexion she says came from her maternal grandmother who was of Indian descent. She said premature greying is a family trait, and she's had snow white hair since she was about thirty. Her daughter convinced her to try some of the bright tints, so she usually has electric-blue or emerald-green streaks in her hair, chosen because her eyes seem to change from blue to green depending on the light and her mood. Her skin is still flawless, so she looks like a college girl sporting trendy locks.

"Natalie washed herself in a matter of seconds, and then she was helping me dry off. Again, she only took a few seconds for herself. From there, she led me to my bed where she had me sit on the edge, draped in a warm, dry towel, while she brushed my hair for me. I was feeling totally pampered. When she was done, she put the brush away, came back and gave me a soft kiss, and then turned as if she were leaving."

"I caught her hand and pulled her back to sit in my lap. I hugged her to my body and stroked her hair for a moment before I leaned in for a real kiss. She responded as I'd hoped, kissing me back, opening her mouth for my tongue and swirling her own tongue around its tip. I realized then the truth about women kissing differently than men. Her mouth was soft and gentle with only an occasional nip or hard nibble. Her tongue fluttered more than stabbed. And she made these adorable moaning sounds."

"From there, we rolled onto the bed. Neither one of us had ever been with another woman before, so it was awkward but fun exploring each other's bodies and trying to figure out how to play with someone else's nipples and pussy. Natalie was great about telling me what she liked and didn't like, and she was open to me telling her the same things."

"I think we both like having a nipple in our mouth, because we spent a lot of time in a nipple sixty-nine. We got each other off with our hands, and by rubbing our pussies together, but for me they were just warm, comfortable cums. It seemed like Natalie was just getting started too, but before things went any further, Natalie gave me a kiss and said she had to get home because Roger was going to be arriving with dinner soon."

"We talked today, and I asked her if she'd had rushed off because she didn't want Roger to know she was having sex with me. She told me that it was quite the opposite, that Roger had encouraged her to flirt with me and see where it went, and he was thrilled to hear we'd gotten together. Roger knew she'd had a friend in college who'd made sexual overtures, and that Natalie had been afraid to do anything and later came to regret that."

"When we started working out together, she told Roger how much she admired my body, but over time Roger had picked up on the idea that her admiration was more than just respecting my physical development. Roger started teasing her saying, 'You think she's hot,' and it gradually progressed to, 'You want her.' Eventually Natalie admitted that to herself and to Roger, and he told her to go ahead and see if I might feel a similar attraction."

"After that talk, we made a date to get together tomorrow and see how we like eating pussy. I'll let you know how it goes."

Phoebe had other news. "Natalie told me Scott and Maureen have been swapping with Guy and Karen."

That surprised me, given the fact there's a fifteen- or twenty-year difference in their ages.

Phoebe reminded me of a dinner party where Scott and Maureen had been talking about the kinds of vacation packages they book, and they'd mentioned some of those packages were for swingers' resorts. I remembered the conversation and recalled that there were a lot of questions about those places.

Phoebe said Karen started putting two and two together when she recalled Maureen saying they got to go on most of the vacation packages themselves as business research. They got discounted rates, and they could write off part of the cost as business expenses.

A few days later Karen and Maureen got together for coffee and Karen couldn't resist asking Maureen if their research trips had included the swingers' resorts. Maureen admitted they did, and Karen had a million questions about the resorts and the lifestyle. That led to Maureen admitting they'd partaken at the resort and that she and Scott had become regular swingers. Maureen told Karen straight out that she and Scott had been missing their regular partners and that they'd be glad to initiate her and Guy if they were interested.

In the end, it wasn't hard for Karen to talk Guy into swinging with Scott and Maureen, and it had become a regular thing between the four of them.

I asked Phoebe how she knew all this, and she said, "Natalie saw Karen leave her apartment late one night, and then she heard Maureen knock on the door a few minutes later. Then Roger told her he saw Maureen leaving Guy and Karen's apartment early the next morning as he was heading out to work."