Pam & Zach Ain’t Too Proud to Peg

These are our stories, embellished, but true. The initial seven Pam & Zach stories are in chronological order so that you can get a sense of how the sexual relationship between the two of us progressed. They'd be best understood read in order, but I did my best to make each episode stand alone.

Names have been changed, dialogue and details added for literary purposes, but these events actually somewhat happened.

Future Pam & Zach escapades will follow. But rather than a series, they will be individual events, not necessarily in chronological order, that took place over the ensuing years of our relationship.

Ain't Too Proud to Peg...

Pam and Zach:

Pam:

"It may seem like we are fixated on anal all of a sudden, but I think it was important to tell you in sequence, through this and the previous two stories, how we arrived at the point where Zach wanted me to peg him."

Zach:

"When Pam told me, on our trip home at Thanksgiving, that she had a strap-on harness, well, I wondered if it would be something I would want to do. How would she feel about it? I knew she had it because of a previous relationship she had with another woman. I wasn't sure if she'd be up to using it on me, if that was something I found I would want to do."

Pam:

"In that other relationship, we used the strap-on on each other, but strictly vaginally. When I met Zach, I was still an anal virgin. I mean, I had had a finger up there a couple times, but never a vibrator or a dick."

Zach:

"I was even more so the anal virgin. In all my past relationships, never once did any of the women I dated go there. Until Pam, that is. She opened my mind to the possibilities and, might I say, the pleasures of ass play."

Pam:

"Even though I hadn't known Zach for very long, that day when I blew him outside against that rock, I guessed, that since he didn't object to be nearly naked and getting a blow job in a public setting, he might be up for unconventional sex. I guessed right.

I mean, other guys I've dated were such prudes, compared to Zach. A couple didn't mind me touching their asses, but all stopped short of me putting anything up there."

Zach:

"That first time, in the shower, when Pam did it to me, I mean I really trusted her at that point. I always felt she was much more experienced at sex than I was. And I found I really enjoyed how it felt. How I could feel it through my whole body. How it intensified my orgasm. And, how empty I felt after I came and she removed her fingers."

Pam:

"I knew that night that Zach would eventually come around to asking me to peg him, once his mind overcame the normal questions like, "Am I gay?" or "Does this make me less masculine?"

After I did Zach in the basement and prior to my last story, where I asked him to fuck my ass, Zach had asked me if we could look into pegging. We discussed how we might approach it and we'd also been watching pegging videos."

Zach:

"Yeah, we mainly talked about positions and what size dildo to start off with. Since the basement episode, I knew that I didn't want to start off with anything bigger than the one Pam used then."

Pam:

"As far as positions go, I felt it would be easier for Zach to be on all fours or to hang over the end of the bed so I could do him from behind. But I also really liked the idea of doing it missionary style. That way I can see his face, play with his nipples and be able to jerk him off as well. But I know, that position requires him to hold his legs up and apart and if I want to really take my time, that could be difficult for him."

Zach:

"We thought about, in order to hold that missionary position, using our restraints. We put the cuffs around my ankles and then attempted to tie the straps to the headboard, but the straps weren't long enough to reach."

Pam:

"And as far as what size dildo to use to start out, we decided on one that was 6" insertable and 1 3/4" wide. It's not lifelike, just smooth and purple. The end that goes in the harness has a vibrator that will press against my pussy when I use it."

Zach:

"Pam, go ahead and tell everyone what we did that evening."

Pam:

"Let me just begin by saying that we took a clinical, rather than a lustful, approach that first time. In the future, I'm sure it will become a lust driven part of our sex play, when the urge arises.

We were both naked. I had Zach sit on the edge of the bed and I knelt between his thighs and began sucking his cock and playing with his balls. The strap-on was next to me on the floor along with the lube.

Within minutes, he was rock hard and leaking pre-cum. We were both super excited. The anticipation had my nipples protruding and hard as nails, my pussy already wet.

I told Zach, rather than getting on all fours, to slide down, turn around and face the headboard and lay his chest and upper body on the bed. His knees were on the floor and his ass was in prime position.

I put the harness on, making sure the vibrating end was placed directly on my pussy. I took a handful of lube and liberally applied it to Zach ass, teasing him with my finger, eventually sliding it into his puckered opening.

I lubed the dildo, imagining it as a prick, stroking it like I was jerking off. I moved in close and placed the end against his asshole. I told Zach to reach back and spread his cheeks apart.

I then asked if he was ready. All he said was, "Yes, just go slow."

I raised up on my toes, grabbed his waist and pushed my hips, sliding it easily all the way in. Zach gasped and tensed up, his cheeks clenching tight around the dildo. I held it still until Zach caught his breath and told me to continue.

I started to fuck Zach slowly. Rocking my hips back and forth. I loved that at the end of each thrust the vibrator would send a shiver through my pussy.

I was loving this. I loved fucking him. I loved the feeling of control. I started to pick up the speed of my thrusts. Zach moaned, put his hands above his head and started to buck back against my pushing. My thighs were slapping against his ass.

I lost myself in it, just for a bit, before I heard Zach saying, "Pam. Pam. I'm close to cumming."

I stopped immediately, I didn't want Zach to cum yet. We had decided we wanted to try both positions.

I pulled the dildo out, stepped back and caught my breath. With my hands on my hips, I just looked down at the purple cock and Zach's reddened ass. I'm ashamed to admit, but I felt powerful.

Zach turned over and grabbed his ankles, leaving his ass on the edge of the bed and spreading himself wide open for me. I put a pillow under his head so he could watch, then went and got a towel and two cushions from our couch and placed them on the floor at the end of the bed.

I relubed my faux phallus and positioned myself, kneeling on the cushions between his legs. I guided it into his ass and put my hands on his knees, spreading him wide. As I started to fuck him again I said, "Play with your cock, get it nice and hard for me."

Zach complied.

I took my hands off his knees and started stroking his cock and fondling his balls, all while pumping "my cock" in and out of him.

Zach's eyes were closed now. His hands gripping the sheets. He started lifting his hips to meet my thrusts. His cock was leaking. My thumb rubbing that pre-cum all over the tip.

"Zach. Open your eyes and look at me."

When he did, I told him, "Now play with your nipples and watch yourself cum."

I started jerking him faster, squeezing his balls and slamming his ass with "my cock".

I'll give him credit. He hung on longer that I would have thought.

Finally, he closed his eyes, arched his back and screamed as he shot load after load all over his chest. I kept stroking and squeezing his cock until it was drained, only stopping my assault on his ass when he pleaded, "Stop! Stop! Please!"

As I let go of his cock and pulled the dildo out, he somehow managed to slide himself onto the bed.

I took the harness off and crawled in next to him, placing the towel over all the cum on his stomach, draping my arm over him, kissed him on the cheek and told him I loved him.