The boys go au naturel in the woods and masturbate together. The conversation about pegging continues and Greg gets taken.
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Life’s business got in the way of group playtime for several weeks. Linda and Judy had agreed to the boys going for a hike in a nearby state park one Sunday. It was understood that they would engage in some type of sexual activity during the day. The Closed Loop Relationship agreement required full disclosure, which they readily shared with their spouses that evening. The park had been crowded and it was necessary to hike for several miles to find some solitude. They stripped off their clothes and stuffed them in backpacks. Then put their boots back on. They walked in solitude for a couple of hours. Talking about erotic things, desires, and fantasies gave them hard-ons and both enjoyed walking with their cocks bobbing and watching their buddy’s cock in play.
Mac talked about agreeing to get pegged and his concerns. He had described how hard they fucked when Linda was receiving. His worry was she would pound him like that. Greg expressed support, sharing with Mac, Judy was probably going to push it along with him too. They also talked about regular things, just enjoying each other’s company. Ultimately, they only jacked-off, while the other watched. It had been a thoroughly enjoyable day. They got back home in the late afternoon.
Linda was stunned about the ‘public nudity.’ Mac had told her about the day, and she couldn’t believe they walked around in the woods naked. “What if somebody had seen you?”
“I dunno. I guess we would have waved and kept hiking.”
“They could have reported you to a Ranger.”
“We were way out, miles away from the campground and the Rangers. We never saw anyone near us or far away. It was exciting to be naked in the woods. It wasn’t really that risky and we enjoyed it.”
“What did you talk about?”
“The same sorts of things we talk about when we have lunch… work, sports, politics, and exercises we might try at the gym. To be honest, we did talk about some sexual fantasies that gave us erections.”
“Is that when you masturbated?”
“No, we just kept walking. It was pretty cool to watch our cocks wobbling around as we moved. We did talk about pegging…”
“Ooh, are you both ready?”
“Sorry, but we’re both hesitant. But, you know, never say never.”
“I paid over a hundred dollars for a strapless dildo, and I’ve been doing Kegel exercises to strengthen my pelvic floor muscles to hold it in place. We can both get stimulated while we’re having sex. I don’t want to wait too long.”
“Alright, let me think about it some more.”
“Sure, honey. I can’t wait to peg you to the bed,” she said with a big smile.
When Greg told Judy about the day, she was surprised. “You spent several hours together naked and all you did was spank your monkey, while Mac watched?”
“Yeah, but I also watched him jerkoff and we talked about a lot of stuff.”
“I get it. But you’re not giving me anything to fantasize about while I Jill off.”
“You don’t need to Jill off baby, I’ll give you the real thing.”
“OK, let’s get our babies bathed and put to bed. Then we can have a romp.”
Later when the kids were in bed and Greg had used his ‘Magic Tongue’ to give Judy an orgasm, they settled in to extended cuddling and petting. They often shared this kind of intimacy to unwind and be together with no sexual agenda. If one felt the need for an orgasm, the other would joyfully help. But often they just touched each other and talked.
Judy was idly playing with Greg’s balls, and he had been semi-erect for twenty or thirty minutes while they talked about the logistics of life. Changing the subject, she observed, “The two times I’ve watched you with Mac, both of you have inserted fingers in the other’s ass. And I’ve also done it to you with pronounced effect.” She felt his cock brush against her arm as it grew.
“It obviously turns you on. But when I bring up the idea of pegging, you freak. I think if we did it right, it would be enjoyable for both of us. I’m interested or I wouldn’t bring it up. And this (she pushed his now hard cock in a downward direction) suggests it might turn you on.” She let go and it pushed back against his leg and then stomach.
“Sold out by my own cock,” he chuckled. “OK, I confess. It’s very erotic and I’ve known it for a long time. I kept quiet about it because I feared it meant I was gay. That was a sound theory for a teenage brain. That’s where ‘they’ have sex because it feels good to ‘them.’ Mac and I masturbated together often in our early teens. But when we got in high school, we probably both thought something along the line of ‘real men don’t do that together.’ So, we stopped. We didn’t talk about it. It just stopped happening. When we were in college, I masturbated in the shower most often. Soap is a good lubricant, and I often shot a load with a finger up my ass. I never used anything bigger, like a vibrator or dildo. Times change and I understand more about myself. I can also be more honest. One of the reasons I haven’t shown interest is a part of me believes you will think less of me.”
“How could you think that?” Judy sounded a little hurt.
“It’s not about me thinking you’re judgmental. It’s about me judging myself.”
“So it’s preemptive behavior. ‘I believe this, and she might too.’ Fear of being outed?”
“Yes, that is probably the thought process,” Greg admitted.
“But you said, ‘times change.’ Do you still think I would believe you’re gay?”
“Not now. If I peel another layer off the mental onion, I realize it’s probably fear of pain. I’ve tried to insert two fingers at times in the past and it’s uncomfortable. Basically, one finger is great; two not so much; anything bigger unimaginable. The idea of you pounding away with some giant dildo in me, isn’t an erotic dream for me.”
“I think you need an anatomy lesson, my Love. The sphincter is a muscle. A tight muscle is a force to be reckoned with. When the kids were younger, and we were feeding them. Did you ever try and force a spoon in their mouth? I know it’s not superlative parenting but getting that nutritious slop in their stomach was a box that needed a check mark. Force feeding a one-year-old is a challenging task. It takes time and encouragement. I don’t know why I have used my adorable children as a lesson in anal sex. It does illustrate the point.”
“And the point is…?”
“When you were in the boy’s shower at college, trying to jerk one off quickly, you didn’t take a lot of time to prepare yourself. Someone could have pulled the curtain open and discovered you. A soapy finger went in easily. You tried two fingers and met resistance. Never mind, one will do. Good anal sex takes time,” she concluded.
“Wait, we’ve never tried anal sex. Is this lesson care of Cosmopolitan Magazine?”
“How many dildos do I have?”
“Two.” Judy waited.
The light went on in Greg’s eyes, “Oh my God, you use one…”
“Yes, I do. And I love the feeling of double penetration. Now I want you to update your anal experience. You’re not a teenager anymore.”
“Now, tonight?”
“Why not? You’ve had a shower. The kids are asleep. You’ve only had one orgasm today… that I know about anyway. Now is a wonderful time. Come on. Pull the sheets back and get on all fours. I’ll get the stuff.” Judy threw the covers back and opened her bedside table.
Greg overcame his resistance and did as he was asked.
Judy brought the ‘stuff’ to the end of the bed. She slapped Greg on each butt cheek and then kissed and licked the red marks. She put a large towel under his knees. “I know you’ve watched me Jilling off with my vibrator. But the one I use for double penetration is smaller.” She showed them both to him. “This smaller one is what I will use on you. See how small it is at the tip? Then it gets wider to slowly spread you open, but it quickly gets smaller, allowing the sphincter to close around it. When you feel the muscle shut, it’s in.”
“OK,” Greg said a bit nervously.
“I’m going to do this slowly. If something is uncomfortable, just say, ‘wait.’ I won’t rush you.”
“OK”
Lube was copiously applied and gently rubbed around. Greg was still semi-erect, and she transferred some lube from her hand to his cock by stroking him, until he was hard. She showed him the vibrator and turned it on. Still standing at the side of the bed, she reached over and slid the vibrator up and down his shaft. Greg trembled at the sensation. He liked ball play and she pulled his sack down with one hand and moved the vibrator over his testicles to his delight. Moving back to the end of the bed, she reached between his legs and tugged and massaged his entire package with one hand, while working the vibrator around the area.
“Keep that up and I’ll cum for you quickly,” he said in a husky voice.
“Your nuts are still hanging low. I’ll get you close, but you’re not going to bust one quite yet.” She moved the vibrator to his ass crack and began stroking from the top of the crease to his nuts and then back up. With her other hand she seized his cock and pulled it back parallel to his thigh. She stroked him in this position for several minutes. He was moaning happily, and the scrotum pulled its nuts up tight… he was close. She stopped stroking his cock and let it spring back up to his stomach. He quickly reached back to grab it. “Not yet. Leave it alone for a while.”
Greg groaned, “Yes Ma’am.”
She spread his cheeks, fully exposing his asshole. “Twinkle, twinkle little brown star; now I see just where you are. Wish I may and wish I might have me in you this very night.”
Greg laughed out loud. “You’re a poet and didn’t know it.”
“Thank you, thank you very much. I’d like to thank my husband. Without him this award wouldn’t have been possible.”
They both laughed, but the moment passed immediately when she placed the tip of the vibrator on his ‘brown star.’ Greg gasped. She circled around the edges a few times and then gently pushed the tip against the resistance. There was plenty of lube to push in, but she waited. She kept the gentle pressure up, while reaching down and grabbing his nuts. The scrotal sack had loosened after the ‘almost’ orgasm passed. She pulled back, stretching the sack further and Greg grunted. She pushed the vibrator past the opening about a half inch.
“Oh my God! Wait!”
She held steady but didn’t withdraw. Releasing his nuts, she played with his cock. She could feel him relaxing and very slowly pushed a bit further in. He didn’t say anything, so she kept sliding in.
“I’m feeling some pressure, but not pain,” he observed.
“Push against it.” She felt him tighten and she moved the largest part of the vibrator inside him. The tightening muscle clamped shut around the smaller shaft. “We’re in. I’m going to turn the vibrations up now.” There was the right amount of lube, and the vibrator was moving easily. She tilted the back end of the vibrator up, allowing the tip to tilt downward for better contact with his prostate.
Greg shuddered with pleasure. “Oh my god! Is that my prostate?”
“Jesus Greg! I’ve got a vibrator in your ass. Not a proctoscope. I can’t see inside. The prostate was what I was aiming for and by your reaction, I think I found it.”
“Sweet baby jesus, that feels divine. Yes, keep that up.”
“I want to watch your face. Give me your hand. Right, place it on the end of the vibrator to hold it in. Now roll over on your back. Good, now scooch up a little, a little more. Perfect! Now pull you knees up and hold them there, no higher. Great! I want to drive this pleasure trip. You hang on to your knees.”
Greg was now laying on his back with knees pulled back, exposing everything a bathing suit hides. He had a vibrator sticking out of his ass with his wife at the controls. He was completely exposed and had ceded control to his wife. He LOVED it!
Linda held the vibrator on her labial lips near the clitoris. She laid her free hand over Greg’s cock. When she was pushing the vibrator in, her hand pushed up on his cock. As she pulled the vibrator out, her hand moved down his cock to his balls. She kept this dual stimulation coordinated by her slow humping. It was a good arrangement, since she was getting a buzz. It helped a lot seeing Greg’s reaction. He appeared to be in a state of bliss. He was pushing back against the vibrator, taking it in all the way to where Linda was holding it. He was making all kinds of happy ooh and ahh sounds.
Judy took her time. The vibrator teased her clit but wasn’t stimulating her enough to reach orgasm. Consequently, she was in no hurry. Watching Greg’s reactions was a big turn on and she slowly began to feel she might make an ‘O.’
Unfortunately he was rising up to the edge, and started talking, “Fuck me baby! Fuck your boy toy! Stick your big cock up my ass… all the way.”
Linda smiled. Another avenue of stimulation to get to her ‘O.’ “Take it baby boy.” She thought she might make it. “Take my big cock all the way inside your sweet, sweet ass.”
Greg came. ‘Dammit,’ she thought, ‘so close.’
When he ejaculated, he let go of his legs and grabbed his ass. He shuddered and shook but the only sound he made was a long “Mmmmmmmmmmmmmm.” Linda released his cock. It jerked up and down, left and right, spitting cum far outside the protection of the towel. As all orgasms must, his ended gradually. The cum stopped coming, but the cock still jerked, and shudders ran through his body for a few moments.
He opened his eyes and looked at Linda, “I’m yours. Anytime you want to fuck me, I’m yours.”
“I will take you up on that offer. But, right now, I need the use of your mouth and tongue.”
Greg licked his lips, “Come and get it.”
Judy dropped the vibrator on the bed and crawled between his legs, licking cum along the way. Since he had sprayed in virtually a one hundred eighty-degree half-circle around his crotch, she didn’t try cleaning him, as much as, making a path toward his lips. “I want to ride your face,” she said lustily.
Greg moved down on the bed a bit to allow a place for her knees. She arrived and settled her moist labial lips over his mouth. Rocking and grinding, she used him for her pleasure. He lived up to the moniker ‘Magic Tongue’ and her orgasm was quick, deep, and hard.
Afterwards, they lay close touching each other and kissing. Greg figured he needed to fill Judy in on the pegging discussion, since the CLR required open honesty. “I just remembered something else we talked about.”
“What’s that?”
“We talked about our fears of pegging.”
“Do you still have fears?”
“I told you, ‘I’m yours.’ I meant it.”
“I’m really happy you enjoyed it. I didn’t use my new purchase.” She reached in her bedside table and pulled out a purple ‘L’ shaped dildo. “It’s strapless. Obviously, this penis-like end goes in you. It’s the same size as the vibrator we used tonight. This part goes in my vaginal canal, so I get stimulated while I’m doing you. Linda and I bought them a couple of weeks back. We’ve both been doing Kegel exercises.”
“Honey, if your pelvic floor gets any stronger, you’ll crush my cock,” he smiled.
“The lovely older woman at the store told us it is uncomfortable if you can’t hold it in place. I just want to be able to pleasure us both when I use it.”
“So, Linda has one too?”
“Yes, why?”
“Mac is concerned because when they have anal sex, Linda asks for a pounding. He’s worried she will do that to him.”
“I hope he’s got the balls to tell her about his concern.”
“I’m sure he will. But Linda evidently seems to get, how shall I put this, overly enthusiastic during sex. He worries she will forget his concerns in the heat of the moment,” Greg said tactfully.
“Mac thinks, Linda will go crazy and fuck him into the next century.”
“Yeah, something like that.”
“Well, obviously that’s something they need to talk a lot about. I don’t think it would help for me to say anything to her. It would probably hurt her feelings.”
“He probably did tell her already since we talked about it today. We both want to be open and honest.”
“I guess Linda will probably call me tomorrow. Let’s get some sleep, lover boy. We both have to go work tomorrow.”