Overnight Playdate

**Secretcumlover** · Sep 14, 2024, 1:44 PM

In my mid 50s and having probably a dozen encounters in my adult life most were just a quick hookup and we bot
h go on our way. I'm still looking for a regular friend to set up frequent encounters with
I envy the guys that have actually got the chanceto play with a roommate in bedovernight.I fantasize about having that "friend" where overnight encounters were possible. Being in one of our houses, or even a hotel room with total privacy and no time limit. We hang out and maybe have a few drinks to ease the nerves.We take our time sucking each other off, edging each other over and over.
We go to bed totally naked with each other and him behind me no our sides . Whether right away or sometime in the night feel him spooning up against me. Feeling his hard cock pressed up against my ass. I wiggle my ass against him as his cock is vertical between my cheeks slowly sliding up and down. Him grabbing a nice slippery oil and lubing up his cock to make things nice and smooth. I picture this going on for quite some time.. me grinding against him as I stroke my own cock feeling his cock gliding over my waiting asshole . Then the moment comes when he's ready to enter my. I feel his lubed head pressing firmly against my opening. My wiggling sde to side while I push back towards him feeling him stretching me as he slowly slides inside. Totally relaxed with no chance of anyone catching us. Then the slow fucking begins..all the way in and out just leaving that swollen head inside me. Feeling his hands on my shoulders as I reach back and spread my ass cheeks open for him. Feeling his hot breath on my neck as he fucks me. Me pushing back and grinding my ass towards him until he's fucking me hard and fast and shoots his hot cum deep inside me. That scenario is so hot to me. We obviously finish up our visit in the morning with a nice shower and him feeding me his load for breakfast.
I'm sure there's many of you on here that have had that opportunity and hopefully don't take it for granted. I'd gladly take your spot for a night!

**colfax129** · Sep 14, 2024, 7:02 PM

It would be fun to be able to suck several times throughout the night.

**Secretcumlover** · Sep 14, 2024, 7:45 PM

Originally Posted by colfax129

It would be fun to be able to suck several times throughout the night.

Totally agree! The biggest part is not being rushed and total privacy..not like a quick blow and go in a parking lot. I responded to your message but not sure you got it. I received your message about your new location. You're still close enough to make this fantasy a reality! Maybe not overnight but an all day thing with a nap date

**colfax129** · Sep 14, 2024, 8:11 PM

Could meet at the pub for a beer, then take it home if we feel like it. Sent a number.

**remington12369** · Sep 15, 2024, 2:28 AM

I am one of the lucky ones. I been lucky enough to have had 2 overnights with my lover. One was in his man cave and we retired early after sex because we were going hunting the next morning. The second time we stayed up late, went to bed and he made sensual love to me. The next morning with his cum still in me he spooned me and slipped his cock in my ass again. He fucked me with his elderly mother sitting in the living room just around the corner.

**dicktrobing** · Sep 15, 2024, 3:35 AM

I've had a few overnights with guys, it is hot waking up in the middle of the night and sucking on your bed mates cock and him having a wet dream

In the morning while having a shower bending over to pick up the soap and being fucked

**cajunman696960** · Sep 15, 2024, 9:59 AM

Originally Posted by Secretcumlover

In my mid 50s and having probably a dozen encounters in my adult life most were just a quick hookup and we bot
h go on our way. I'm still looking for a regular friend to set up frequent encounters with
I envy the guys that have actually got the chanceto play with a roommate in bedovernight.I fantasize about having that "friend" where overnight encounters were possible. Being in one of our houses, or even a hotel room with total privacy and no time limit. We hang out and maybe have a few drinks to ease the nerves.We take our time sucking each other off, edging each other over and over.
We go to bed totally naked with each other and him behind me no our sides . Whether right away or sometime in the night feel him spooning up against me. Feeling his hard cock pressed up against my ass. I wiggle my ass against him as his cock is vertical between my cheeks slowly sliding up and down. Him grabbing a nice slippery oil and lubing up his cock to make things nice and smooth. I picture this going on for quite some time.. me grinding against him as I stroke my own cock feeling his cock gliding over my waiting asshole . Then the moment comes when he's ready to enter my. I feel his lubed head pressing firmly against my opening. My wiggling sde to side while I push back towards him feeling him stretching me as he slowly slides inside. Totally relaxed with no chance of anyone catching us. Then the slow fucking begins..all the way in and out just leaving that swollen head inside me. Feeling his hands on my shoulders as I reach back and spread my ass cheeks open for him. Feeling his hot breath on my neck as he fucks me. Me pushing back and grinding my ass towards him until he's fucking me hard and fast and shoots his hot cum deep inside me. That scenario is so hot to me. We obviously finish up our visit in the morning with a nice shower and him feeding me his load for breakfast.
I'm sure there's many of you on here that have had that opportunity and hopefully don't take it for granted. I'd gladly take your spot for a night!

I would love to find someone to do that with, it sounds so hot �� and mad me horny just reading it

**dowmass** · Sep 15, 2024, 4:14 PM

This is just a dream that hasn?t come true.
i wish I had a lover that I could completely surrender to.. skin to skin, not even a barrier like the flimsiest condom coming between us.
He can host, being all by himself, and we kiss for several minutes before I move down to his boxer shorts. He?d all commando underneath and I can feel his 8 inch manhood eagerly waiting to come out. I pull his shorts down and I see the most beautiful thing on the planet? a very hard cock and a pair of nice balls underneath. Before he can even say ?hello? I have him in my wet mouth. Now there?s no escape from my luscious lips and the next thing you know, I am devouring the cock like there?s no tomorrrow.

Before long I am on all fours and can feel his cock enter the rim of my man pussy, and goo all the way in. In that doggie position I feel like a shy submissive bitch in heat. I keep telling myself that this shouldn?t end, because each time his cock hurts my prostrate, it sends me a wave of pleasure.. He goes on for almost two hours before he yells OH.., I AM GOING TO CUM..

**Orgasmus** · Sep 15, 2024, 5:34 PM

It took me 13 years to find a like-minded buddy who was open to an ongoing FWB relationship. Dave and I have been together six years now and have enthusiastically explored a special level of sexual intimacy that's only possible between two open-minded guys.

Because Dave is separated from his wife, Deanna, we can pretty much be assured of complete privacy and extended play sessions that leave us both well satisfied. I've only allowed him to fuck me eight times in total -- and that includes two times the first night I surrendered my anal virginity. But we've explored pretty much every other imaginable form of guy-on-guy sexual expression, and I'm hopeful the uninhibited explorations will continue for years to cum.

**CockHummer** · Sep 15, 2024, 7:35 PM

Do you stop to think about the fact that he is cheating on his wife with you, and does that turn you on, like as if to say you've got a guy who'd rather fuck you than his wife?

You say it took you 13 years to find him, but how did it happen?

Did you go into it knowing that you wanted his dick up your ass?

Do you get horny thinking about him when you are not together?

**Orgasmus** · Sep 15, 2024, 11:20 PM

Well, since you asked CockHummer . . .

Dave and I met online and connected over our mutual interest in nudism and naturism. We began exchanging nude photos and explicit emails, and that led to these wonderfully uninhibited Skype sessions where we would watch one another masturbate on cam. One warm day in May, Dave invited me out to his secluded home in the lake country about an hour west of here for a nude hike through in his 20-acre woods and some hot tubbing. I fully expected an in-the-flesh encounter would turn sexual, and predictably, it did.

Dave and I seemed to have similar sexual interests, and our playdates became sort of a weekly occurrence. Dave was a bisexual newbie at that point. That is, he'd never played sexually with another man before, but being separated from his wife, Deanna, for two years, he was eager to explore different forms of guy-on-guy sex. One by one, we began crossing things off his rather large bucket list ? mutual stroking, cock-to-cock play, oral sex and ultimately anal sex.

No, I never had any particular interest in bottoming for Dave, and it?s still not something I look forward to doing. Okay, I'll concede some initial curiosity about what anal sex might be like. I'd been pegged once and wondered how the real thing might feel. However, I only agreed to let Dave fuck me because I felt a certain emotional bond between us and wanted to fulfill his fantasy.

Since you raised the issue of cheating, I've never really seen it as such. Okay, on those rare occasions When Dave and I are together it seems more like two friends helping one another accomplish something they'd do by themselves anyway. One important distinction is that our relationship is largely sexual. Yes, we have an unconventional friendship, but if other emotions were involved, that would seem like cheating.

Dave and his wife, Deanna, are separated, in part, because of his evolving interest in bisexual play and his desire to involve her in it. As a retired dentist, Dave is well-to-do and not particularly eager to pay his wife a seven-figure divorce settlement. Thus, he puts her up in a luxury apartment about 10 miles from their lake home and they lead a rather unconventional coexistence. Dave and Didi still get together and husband and wife now and again, so I'm not supplanting her.

By the way, Deanna has met me several times. We've had dinners together, gone to a couple of social functions together -- and she generally knows her husband and I have a FWB relationship, although I'm pretty sure she doesn't know to what extent. In fact, our first meeting was when she dropped unexpectedly by and saw the two of us scampering naked across the deck.

Do I get horny when Dave and I aren't together? That happens occasionally, but not as much as it did when we were new. Hey, we're both 60-something guys and our libidos aren't what they used to be. This summer Dave and I only got together maybe five times. Occasionally he'd message that he'd love to stroke my cock, or have his sucked, and that'd get me fantasizing about things we've done together, or about things we've talked about doing. But I guess that's only human, no?

**Orgasmus** · Sep 17, 2024, 1:24 PM

No, CockHummer, save for friendship with a guy who shared certain of my personal interests, I did not go into our relationship with any particular expectation -- least of all having his dick up my ass. Based on our previous online encounters, I had a pretty good idea a face-to-face encounter might turn sexual. I figured that might involve Dave and I just hanging out together nude and jerking ourselves off in one another's presence, It quickly evolved into something more.

For what it's worth, having Dave's cock in my ass was the last thing I ever expected to experience, let alone enjoy, but one night after tequila shots in the hot tub, inhibitions were way down. Dave turned to me and asked rather matter-of-factly, "Would you ever consider letting me fuck you?" The question surprised me, but not as much as my answer. "Sure," I said, "Let's go!" The next I knew we were scampering bare-assed up the stairs to Dave and Didi's bedroom.

It probably bears mention that I have never enjoyed being fucked. It's never been pleasurable for me; just a lot of pressure, and uncomfortable sense of fullness and occasional pain that I could easily do without. In total, Dave and I have only had anal intercourse seven or eight times, and I have only ever consented to participate because Dave was insistent and felt some obligation to allow him that pleasure. If there has ever been any enjoyment in it for me, it's has been seeing the waves of pleasure reflected on his face while I ride his cock and feeling him twitch and throb and hearing him moan as his orgasm washes over him. Dave has on a couple of occasions offered to bottom for me, but I have no particular interest in that.

**DLazguy** · Sep 17, 2024, 6:26 PM

I would like to experience a full night or even better, a weekend of all day playing. The thought of being able to roll over and start sucking a dick throughout the night is amazing. Or to have him roll over and start sliding his dick into me and wake me up with a hard surprise (fortunately, I sleep on my stomach). I really want to experience a day or two of nothing but sucking and fucking.

**Secretcumlover** · Sep 17, 2024, 6:56 PM

Originally Posted by DLazguy

I would like to experience a full night or even better, a weekend of all day playing. The thought of being able to roll over and start sucking a dick throughout the night is amazing. Or to have him roll over and start sliding his dick into me and wake me up with a hard surprise (fortunately, I sleep on my stomach). I really want to experience a day or two of nothing but sucking and fucking.

This is exactly what I'm talking about!!

**colfax129** · Sep 17, 2024, 9:57 PM

That WOULD be fun!

**Secretcumlover** · Sep 19, 2024, 4:54 AM

Originally Posted by colfax129

That WOULD be fun!

We should try it sometime! Or at least an all day session and see how many times we can get each other off. I'm game!

**Orgasmus** · Sep 20, 2024, 1:24 PM

Originally Posted by DLazguy

I would like to experience a full night or even better, a weekend of all day playing. The thought of being able to roll over and start sucking a dick throughout the night is amazing. Or to have him roll over and start sliding his dick into me and wake me up with a hard surprise (fortunately, I sleep on my stomach). I really want to experience a day or two of nothing but sucking and fucking.

Okay, I can't believe I'm going to admit this, because I’m pretty reserved sexually, but six years ago when we were still quite new, the opportunity arose for me to spend an all-nude weekend at my friend Dave's place.
That Friday afternoon, before arriving at Dave’s house, I stopped down the road, wriggled out of my out of my nylon running shorts, tank top and flipflops, then drove into his yard completely naked. Dave met me at the backdoor also completely nude – and semi erect -- and neither of us never wore anything but a smile again until Sunday night.
The plan was to get sexually better acquainted. That is, to have sex as often as possible and in as many places and in as many ways as possible all weekend long. And we did -- in his private 20-acre woods, on his big redwood deck, in the hot tub, by the bonfire, on a tire swing, in his bedroom, in the kitchen, on the three-season porch . . .
I hadn't allowed Dave to fuck me yet, but in 52 hours together we got one another off at least a dozen times via mutual masturbation, cock-to-cock play and oral sex. And yes, because someone'd bound to ask, we slept naked together in the same bed and took turns waking one another for impromptu midnight play sessions.
I drove away feeling AFO and surprised at the level of intimacy I was able to share with another man.