Empty Nest Escapades

This story is focused on the male on male piece of the encounter, if this is a bother for you do not continue, if not then enjoy. Thank you, LarryinSeattle for his efforts in making this much more readable.

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Doug finished his shower, dried himself, and went to check on the two lovers. Seeing them still cuddled up in each other's arms asleep, he started to gather his clothes to dress and leave. As he bent over to pick-up his shorts, he heard a soft whistle. Turning, he realized Bill was awake and staring at him with a small grin.

"Leaving so soon?" he asked quietly, trying not to wake Jennifer.

"I didn't want to disturb y'all," Doug replied.

Bill gingerly slipped loose from Jennifer's grasp, careful not to disturb her and reached for Doug's arm, stopping him.

"Don't go yet," Bill said as he slipped to his knees and took Doug's soft cock into his mouth.

Licking around the head and then sucking it deeper into his mouth, Bill felt the flesh start to harden and felt Doug's pulse as the blood flowed into the tissues, stiffening it, making it grow. Bill continued to minister to the now hard cock as his hands slowly moved up Doug's legs, one hand cupping the low hanging sack with its soft, oblong, balls. He then started rolling them around in his fingers. The other hand reached around behind and started massaging the firm, lightly haired cheeks of Doug's ass.

Bill pulled back to take a breath, moved his hand back around to the front, and lightly stroked Doug's hard cock. He wetted his fingers with the saliva and precum that had been leaking from the head of Doug's hard organ. He slipped it back around behind and between Doug's firm cheeks. Pausing briefly with his finger against the pink ring of flesh, Bill pressed more firmly and felt the flesh give. He slid his finger in to the first knuckle. Doug gasped quietly and Bill took him back into his mouth as he continued to slowly penetrate Doug's ass.

Bill went deeper and found his goal, the same firm, walnut sized ball of flesh that Doug had so well massaged earlier inside Bill. Pressing firmly against the wall of Doug's rectum, he began a come-hither motion with his finger, massaging the firm knot and eliciting another moan from Doug. Simultaneously, he increased the pace of stroking of Doug's engorged cock with his mouth and the firmness with which he massaged his balls, causing another groan.

Bill stayed on his knees in front of Doug, sucking his cock, cupping his balls, and massaging his prostate until Doug couldn't take it anymore and came. Bill, having learned from his first encounter with cum, pulled back until just the head of the cock remained in his mouth. He managed to swallow all but a few drops of the offering. He licked the corners of his mouth where the overflow had dribbled out. He then captured the remainder of Doug's load and savoring the smooth texture and slightly salty taste, he swallowed again and smiled.

Helping Bill to his feet, Doug asked, "Where is that prostate toy you were telling me about in our chats last week?"

Bill reached into a bag next to the bed and grabbed the prostate massager, along with a bottle of lubricant. The lube was designed specifically for anal use so it was not very thick like a gel, but not runny like the liquid type either. Following Doug to other bedroom with his toy and lube, Bill's stomach did a little flip as he started to get excited. He had never used this new toy with someone else since he purchased it, having only used it on himself.

When they arrived at the other bedroom, Doug pulled the sheets down and told Bill to lie on his back with his legs over the edge of the bed. Bill complied with the request and grabbed a pillow to put under his head so he could watch what was happening while Doug grabbed another one to slip under Bill's hips. Kneeling between Bill's legs, Doug started to lick and kiss the semi-erect cock in front of him while massaging the low hanging set of balls below it. With his other hand, he started to stroke the space between Bill's sack and his anal opening, lingering over the tight hole and pressing against it gently. Bill immediately began to harden at Doug's touch. Feeling Bill harden in his mouth, Doug reached for the bottle of lube, poured some out on his fingers, and began to spread it around Bill's tight pucker.

After adding more lube to his finger, Doug slowly began to press more firmly against Bill's opening until it started to give and his finger slipped inside. Bill let out a loud moan, cut off for fear of waking Jennifer in the next room. He watched as Doug applied even more lube to his finger and started sliding it deeper into his ass. Before he could even register any discomfort, Doug's finger was in to the knuckle and was starting to be pulled out. Bill was nearly overwhelmed with the pleasure; that feeling grew as Doug started to twist and rotate his finger inside him while pushing it back in. The effort opened Bill up to the point where Doug could slip a second finger inside while kneading his ball sack with the other hand and licking and sucking on his cock.

Bill was as hard as he had ever been in his memory and he felt nearly at the breaking point. Doug, sensing his closeness, stopped sucking and told him to relax, lay his head back, close his eyes, and focus on the pleasure. Bill did as he was told and that's when Doug crooked his fingers inside him and hit that magic spot he had so long wanted, nay, needed to have touched. Stroking his fingers in and out while massaging his prostate on each stroke, Doug felt Bill's body stiffen and his pelvis push down encouraging him to go deeper. As he pulled his fingers completely out, Bill gave another loud moan, feeling empty inside and wanting more.

Doug started to suck Bill's cock again while he prepared the prostate massager Bill had brought with him. Pushing it against Bill's now open anus and inserting it slowly, he heard not just a moan, but a loud groan. Doug smiled as he watched the toy slip inside and once seated as deep as it would go, he turned on the vibration feature. Bill yelped at the intense pleasure that he was feeling and both heard a gasp from the doorway.

Doug turned his head and Bill opened his eyes to see Jennifer leaning against the doorway, one hand spreading herself open and her middle finger buried to the hilt in her pussy. The other hand was pulling at her hardened nipple as she massaged her breast.

"Don't stop, I want to watch," she said with a smile.

Bill laid his head back down and closed his eyes again while Doug continued to slide the vibrating toy in and out of his ass. Doug reached up with his other hand to stroke the hard cock and massage the full ball sack in front of him. Bill started to squirm and moan almost continuously due to the sheer pleasure of the vibrations. The firm hand stroking and massaging him rapidly was bringing him to the brink of a huge climax. Doug pushed the toy deep into him and turned on the rotating head. Holding it in place so that the vibrations and rotation of the toy were focused on Bill's prostate, Doug took the hard cock in front of him back into his mouth and sucked deeply.

"OH, OH, FUUUUUUU...!" Bill shouted as his cock erupted, his cum shooting out of him in a way it never had before. Doug pulled back after the first burst and thick ropes of cum landed on Bill's chest, across his belly and as Doug continued to stroke him and work the toy in his ass, a final shot landed on his chin and dribbled down his throat.

Doug took Bill's softening cock into his mouth and he licked and sucked it, getting the last seepage of cum as Bill lay gasping for breath. From the doorway, they heard a muted scream as Jennifer too had a massive orgasm from her own hands that weakened her knees and left her sliding down the frame to the floor.

Pulling the toy from Bill and turning it off, Doug smiled. Bill still had his eyes closed and his breathing was fast and erratic. Doug helped Jennifer to her feet and led her to the bed. "Hold him, he may need it," he told her.

Jennifer lay down with her head on Bill's shoulder and stroked his head. "I love you. Thank you for making this happen for me," she said to Doug.

And to Bill, she said, "I love you, too, big boy; now let's get you cleaned up." Starting at his chin and working down his neck, chest, and across his stomach, Jennifer licked up the cum he had sprayed. Getting it all, she moved back up his body and kissed him, feeding him the fluids he had so copiously let go.

Doug watched this for a while, pleased to have been able to play a part in such a loving weekend for the married couple He then quietly slipped back into the other room to dress.

Bill and Jennifer continued to kiss and hold one another, oblivious to their surroundings, until they heard the door close. Sitting up, they both went out to see what was going on only to find a note from Doug.

"Thank you both for a wonderful afternoon and evening; I appreciate you letting me be a part of such a loving encounter. I look forward to what the next encounter may bring; you know how to reach me when you want. Good luck with your journey, and know that I had a fantastic time."

Doug