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."
