Panty Diaper Boy & Tomboy Housemates

My Ass Never Felt Better

That afternoon with Ash and I standing there watching the others I could feel her pinky rubbing my hole. She let out slow trickle of pee. She knew I loved her but she was not the mate for me. Mags in a cute short dress and Blue bikini top looked at us. Her beautiful trimmed VJ was just visible.  We both smiled, looked at her, and waved. Mags knew how I felt about her and Ash. I loved them both, but anything like romance with them wasn't for me.

A small dribble escaped from my slender part. As my anus opened just enough for Ash to slip in her small finger pushing my thong aside. Ash often would slide her hand in whatever undies I wore and play with my anus. She knew how to do it in a way that distinguished between a loving comforting touch and sensual arousing probe.  Ash knew what I needed. I walked back inside. Ash followed knowing what I wanted.

I slipped off my flip flops once inside. Ash followed with me occasionally playing with my anus to get it ready. We tickled each other and put fingers in each other's buttholes. I always got hard during this part, but did not want to put it anywhere. I bent over and let Ash pull down my panties and slide the buttplug in me. It feels good when she does it. Mags gets too rough  trying to shove it in me. Ash knew just the right amount of lube to use and how long to finger me before I was ready. Slowly I felt the plug expand my sphincter.

"Is that OK?" Ash asked. She caressed my testes and man parts to calm me.

"That feels great. Just a little more?" I felt the bulb enter me. The plug firmly in me I felt relieved and came a little on the sheets.

"Could you do me next?" Ash asked.

"Sure." I followed paying close attention to be gentle with my finger in her butt.

As we got to her and Mag's room she spread her legs like on an GYN table. All her parts were exposed, but her body to me was not a thing of sex to me. She was just amazingly beautiful. I kissed her beauty and massaged her anus just enough to see it pulse. Her favorite plug was in the drawer next to the bed. It was longer than mine but skinnier at the bottom. I squirted just a little lube on my finger and slid it in her to make sure she was ready.

I slowly slid the plug in her and as the last bit went in she let out a slight "OH!"

I licked the little dribble of cum from her and helped her up.

Plugs in place we went out to the others.

I wondered if there was a man or woman that could be with me as much as Mags and Ash.

With our plugs situated, Ash and I helped each other pick out cute thongs. She picked out one that had an icecream cone on the for me. For her I picked out a simple pink one with yellow lace trim and a bow on the front. I don't know what it is but to me it feels satisfying to have a butplug in me all day long more than any man cumming in me or me in a man or woman. It doesn't usually make me cum without help but I stay semi hard just enough to stretch whatever underwear I happen to have on.

Ash, on the other hand, would almost immediately cum with every step or shift in her seat. It was obvious with the wet spot that turned her pink panties sheer and juices glistening on her inner thighs. She was good at hiding it on her expression but her wet lower body and perky erect nipples gave her away. In fact, she would get so wet that she had to wear at least trainers inside or ruin the furniture. Mags loves being between us massaging us and us her until we all came together. We would sometimes play fight after about who gets to lick whom. The order always was me licking Mags while Mags licking Ash then the girls taking turns licking their ice cream. I always had a few spurts left for them. 

Cheryl and Carl were used to our "Youthful Antics" and usually would play games of their own.

Mildly buzzed, sexually satisfied, with our butt plugs still in place we heard Carl announce...

"Ribs are reaDY!" 

He let out a squeak at the end. Looking up I noticed why. I saw his entire cock in Cheryl's mouth. He clenched his butt cheeks cumming down her gulping throat as she brought herself to orgasm with her hand down her very wet bulging diaper. The three of us let out a little after sex pee onto the deck as we watched them finish up. Without a word all of us cleaned up leaving our panties off and Ash and me butt plugs in. Cheryl had taken her diaper off and was naked from the waist down like Mags and Carl. We had a great meal with wine and beer laughing and carrying on. 

Mags sat between me and Ash with Carl next to me. Everytime I looked at my plate I couldn't help notice Carl getting more and more stiff. I wondered what it would be like for me to take him in my mouth. 

Could I do like Cheryl? He does look sexier than all the one night stands. Would Cheryl mind if I tried?

"MATTHEW!" It was Mags voice and slight tug on his very erect wiener that snapped him out of it. "It's not nice to stare!" she scolded.

Noticing he was caught transfixed on Carl's manhood, "Yes dear, but it's just so mesmerizing." Chastened, he replied, "I just want to kiss it."

"Go ahead." Cheryl gave a response that surprised everyone except Carl. 

Matt watched as a little drop of pre cum formed on the tip of Carl's well endowed member and slowly dribbled down the shaft...

"May I?"

 "Sure go ahead." Cheryl acknowledged.

Carl's spread legs and eager organ showed he had no objection. So, Matt slid under the table and cautiously took it in his mouth. Right away he felt and tasted a spurt of his cum. It was like the others he'd had but this time despite the hugeness of it, it felt gentle and soft.

I felt the probing in my own hole as someone was sliding the plug in and out. Glancing back I noticed that Ash was making love to my anus with my own plug while Cheryl was stroking me and Mags massaging my testes. At some point I managed to get Carl deeper in my mouth and felt him against my throat. The girls had moved the table away and were taking turns slowly probing my ass with a dildo I recognised as one of Mags larger ones. I was getting more and more turned on but nowhere near the ecstasy of orgasm as the dildo and Carl went deeper in me.

I only gagged once when I actually realised that Carl had entered my throat. Then I relaxed as I adjusted and enjoyed it as I felt him slowly slide deeper. It felt great I kept swallowing as my pharyngeal and esophageal muscles involuntarily massaged him. I managed to slide my tongue out and lick his balls and tasted the juices I knew meant he was about to explode.

He arched his back and came full down my throat as I slid a finger in his buttocks. He filled my throat and mouth with juice of his and I could feel it flowing down my tongue past my lips and chin onto his Junk. I tried to catch it with my tongue and managed to lick him all the way to his anus. Setting off a final spurt as he pulled out filling my mouth and letting his juice flow on my chin it was then I realized The girls had managed to get the dildo all the way in me and it felt great, I had never had something that in in there before. I reached back stopping them from pulling it out trying to shove it in further. But, there was no more left of it I felt the artificial balls against my gonads.

Frustrated, I turned my open eager hole to Carl hoping he had more in him. He immediately got the hint and I felt his long hard cock slide in me and begin thrusting. Still, this was not enough. I had done this before normally I would guide a Ashley under my horny member, but I though Cheryl was the better choice. I reached for her and she did not resist, but to my amazement guided past her vagina into her anus. While I trust in and out of her I felt a steady stream of warmth fill me and flow across our genitals. Carl was using my butt for his urinal. He was still hard and his urine flowed out and around us and I let my cum go in his wife's ass. She shrieked and an explosion of juices came from her crotch. The three of us slumped together as I felt Carl slow to a trickle and we all gave out the last little spurts of sex. I could still feel Carl's diminishing erection letting out the last of his pee/cum in my ass as he said...

"Thank the gods for Viagra."

Ash was sitting on Cheryl's face, Mags had mounted Carl with a strap-on, my spent dick was in his wife, and his was in me. We all rolled apart and had a great laugh and continued our evening letting our sex juices drip out of each othere's oraficases.

Late that evening as I was putting on my diaper for bed I thought. "My ass never felt better!"