Meet Their Eyes

Several hours later, and after a lost bet, we were waiting for food and drinks at The Greasy Pig. I was fidgeting because I had a plug in my ass. I watched Jesse give a flirty look to the large Saurian barkeep and say something that made him chuckle. He handed her the beers she had ordered and she had a little extra sway in her step on her way back. She handed me mine as she sat down and took a swig of her own.

"I can't believe you made me wear this plug out of all the ones I own." I grumbled under my breath before taking a large glug of my beer. The movement was rigid and unrelaxed as I tried to keep the plug tip away from my prostate.

"You're the one who accepted the bet." Jesse said smiling from ear to ear. "It's not my fault you can't help but cum over a pair of soapy titties."

It was true, I shouldn't have taken that bet in the shower earlier. But considering I had already cum I figured I could last a full minute without cumming. To my credit I did, but then she offered double or nothing and the second full minute she had me dead to rights. "You cheated." I said flatly, "we never said you could use your tongue as well."

"To be fair we never said I couldn't use my tongue either.", Jesse slid a little closer to me and slid her hand to the small of my back and whispered in my ear. "I could go under this table right now and give you a little tongue but we both know your cockhead is taken at the moment."

I grinded in the seat but still kept the plug away from my prostate somehow. What Jesse was referring to was this specific plug had a lengthy attachment that magically sealed to the head of your cock. So any cum you produced when the plug finally grasped your prostate with its tentacles and started milking you the cum you produced was pumped directly back into your own ass. This isn't that big a problem with most races but if you are a very big producer like I am, things can get very full very fast. Reasons I was trying to keep the plug away from my prostate currently. Once it got a hold I would be biting my tongue to hold in my moans.

"Let's just order and be done so I can go get some sleep in an actual bed for a change instead of your couch or a bedroll in the woods." I said grumpily.

"Hey you love my couch," Jesse said then leaned in and whispered, "I remember some very good prostate milking happening on that couch." She slid her hand down the back of my sweats and her index finger pushed on the plug and changed the angle slightly. I grunted and tried to shift away, but she kept up the pressure. Her mouth stayed close to my ear, and her other hand grabbed my arm to hold me still, "Easy baby. You know you want this. To get milked like a good breeder in public." Her voice was low and sultry. Her finger pressed harder and the plug's tentacles finally found my sweet spot.

"Oh fuck!" I said, just as the waiter walked up. The human woman was a petite little thing and even with me sitting she had to look up. Her face had a confused expression on at my outburst but Jesse intervened as I gripped my own fist in front of my face.

"It's okay," Jesse said, "I know you hate forgetting your wallet but I told you tonight was my treat anyway." She looked at the waitress, her hand sliding back up to my back. "We will have the fried pickles to start and I want your Bourbon burger and fries, and sweety you said you wanted the...?" She trailed off and looked at me with a smirk on her face.

"Just the, mmghch, steak and baked, grch, potato." I gave the waitress a forced smile, as I struggled through the words. The plug was slowly squeezing my prostate now and I could feel the cum build up inside my cock.

"I will get that right in for you. Shouldn't be but a few minutes." The waitress said before turning away and walking towards the kitchen.

Jesse's hand slid around into my lap and began stroking me through my pants, "Now where were we? Mhmm, yes you being a good milking stud." My cock responded immediately and began growing fast. My pants tenting as I reach about half mast when the part of the plug that gripped my cockhead magically extended and gripped the rest of my shaft and balls. It formed a hardened cage around them. "Mhhmm that was fast...now all you can do is be milked slowly. Now that you are locked in your cage."

I was trying to breathe and not immediately run out the door of the restaurant. She knew all of my buttons damnit. I really shouldn't have taken that bet. Over the few minutes we waited on our food, which felt like an eternity, my cock had a steady flow of cum pushing out the tip and into the tube that connected it to the plug. When the waitress finally brought out the food, I could feel my own cum starting to leak into my ass through the plug. As we ate and I filled with more cum the plug swelled as I filled up. Which kept the cum locked inside me, and also put more pressure onto my prostate. This toy was pure torture and I don't know why I ever bought it. Oh yeah, I am a slut that's why. I practically devoured my steak in seconds. My dragon's maw ripping it to shreds without ever needing to touch my silverware. The potato loaded with bacon, sour cream, butter, and all the fixin's went down just as fast. Jesse took her time. Enjoying every bite, and occasionally making a show of licking her fingers. By the time she was finished my legs were shaking with need and my gut had a slight bulge, that wasn't just from the food.

The waitress stopped by to ask if we needed anything else, and Jesse simply said, "No I believe we are both equally stuffed." She then asked for the check, and as soon as it was paid. I stood to leave, just wanting to get home and finally orgasm. What I didn't account for was the poor waitress being basically eye level with my bulge. She looked up at me blushing, and I quickly excused myself as my cock flexed in my pants. I didn't notice her bite her lip as I brushed past and walked quickly to the door and out to the buggy. Jesse practically skipped out of the bar after me, and slid into the passenger seat.

"So, you gonna be a gentleman and drop me off at home?" Jesse asked, as she buckled herself in. "Or do I get to take another shower tonight?"