To truly unnerve him, I would murmur things like “Ohhh, that feels so good” or “Keep that up and I’m just liable to explode.” At one point, I grabbed his head with both hands and started pushing him on and off my dick rapidly. It was like I was fucking his face and you could hear the slurping noise as his saliva escaped his lips. He tried opening his mouth so that there was less contact and I growled “Don’t stop sucking or I’m gonna shove it all the way down your throat.”
After he closed his lips and I face-fucked him a little more, I pulled out of his mouth. It was never my intent to cum during his oral punishment, although I could easily let it happen. As my dick dances before his face and he wipes the excess saliva from around his mouth while looking up at me like a whipped puppy, I ask, “Ready for me to cum in your mouth?”
BOB: “Please don’t. I don’t want that. Didn’t you do enough?”
ME: “It’ll be enough when I cum. Since you don’t want to finish me in your mouth, turn around and bend over.”
BOB: “What? I didn’t think you would do that.”
ME: “What? You were gonna fuck Lily’s ass. It’s only fair I do the same.”
BOB: “But I’ve never done it and your too big to fit. Let me just stroke you and you can shoot it on my face.”
ME: “Turn around bitch. I’ll be gentle and I’ll even use some of the lube Lily had.”
Bob slowly turns and assuming a position with his head on the floor, his asshole is pointed right at me. I grab the lube I had placed by the phone in anticipation of this possibility and quickly coated my cock. Kneeling down behind Bob, I dribbled a little in his crack, allowing it to slowly slide down to his hole. Moving closer, I capture the dribble as it passes his hole and Bob flinches a little at the touch of my dickhead on his ass. While I have done anal with several girls, this will be my first male. I guess you would consider both Bob and I virgins. However, the pleasure I had when Jerry and Tatyana had fucked me as Lily and when Olivia dominated me with the toys, I figured if Bob relaxed, he might enjoy it. Hell, if Tim had been more gentlemanly and we worked together, he would probably got me off while in my ass too. I slide the head up and down his crack smearing the lube and readying myself for the plunge. As I center the tip on his hole and push forward slightly, I say, “Just relax and push back against me. It will fit so just let it in. As it starts into his rear portal, the head, once fat, is squeezed down from the tightness. As I advance, Bob is groaning softly and I repeat “Just relax.”
Looking back he exclaims, “It’s too big. You’re tearing me apart.”
As the widest girth start to enter, I give a quick thrust to get inside. Once in, I sink until my waist hits his butt cheeks. It is amazingly hot and wet feeling with my entire dick buried in his ass. I don’t know why I would think it would feel any different than inside a girl’s ass. As expected, Bob just groans. I slowly extract about half way and then push back in. As I start doing this repeatedly at a nice slow pace, Bob grunts every time I reach maximum penetration. As I fuck his ass, I decide there and then, I’m gonna deposit a full load of my seed in him.
I grab his hips and pull back telling him to get up on all fours. As he does so, the angle improves and I am able to quicken the pace. I look down and watch my shiny, lube-covered cock penetrating his hole as my thighs slap against his butt cheeks with every thrust. Feeling the start of an orgasm, I pull out momentarily to allow it to wane. Before he can react, I shove every inch back into the gaped opening and resume humping. Tiring a little, I stop the full length thrusts and resort to short stabs deep inside him. Bob stops grunting and goes into a slight moan.
After about a minute more, I hear Bob exclaim, “Oh fuck. You’re making me cum. It’s just squirting out.” I can feel his spasms inside and his muscles tighten around my cock. After he relaxes his sphincters he groans, “Oh fuck; that felt so good. I wasn’t supposed to enjoy it.”
As I pick up the pace again, intent on shooting my load, I say, “Let’s see if you enjoy this.” I’m fucking his ass fast and hard when I feel the orgasm rising up and my jizz rockets out my balls, up the shaft and spills into his rectum. I let out an animalistic groan as I shove deep into him with each squirt of my seed. Satisfied that I have emptied myself in his bowels, I extract my now softening cock. As he lays over onto his side, I spy the splotches of cream he shot when I made him cum. I get up and return to the bathroom to clean up. I am deep in thought about my stepping into the world of gay sex. I guess technically, I was only a half-step in since I had not taken a guy inside except as Lily. Bob walks in gingerly and sits on the toilet to allow things to right themselves.
ME: “Maybe next time you coerce someone to have sex with threats, you’ll remember this.”
BOB: “I will never force someone again.”
ME: “Good. Keep it to shagging drunk cougars.”
BOB: “I’m not gay or anything but if you return and want to hook up, you really made me cum big doing that.”
ME; “We’ll see. Now get cleaned up and get out of here.”
Bob scrambles from the room. I didn’t care one iota about getting him canned, as I still had one more kick in his crotch to administer.
Given the events of the past week, Monday was rather mundane walking around the French Quarter. I thought about looking in on Olivia but by the time I strolled by the shop, she was off work. Who knows if she would have even been interested in me as a potential slave? I wondered what would happen if I encountered any of the others with whom I had sex. Since they would not know me, it would be my little secret. While I would have loved taking Vickie to bed and experiencing her pussy from the male perspective, I would hate like the devil if Steve caught us. As evening set in, I even made a point to swing by the bar Tatyana tended. I don’t know whether it was a good or bad thing that she wasn’t there. While I would have enjoyed another night with her, her threat to turn me into a nymphomaniac was none too appealing. So it was back to the hotel I went.
As I headed through the lobby, one of the desk clerks picking up discarded newspaper and tourist guides smiled and asked how my day was going and if I was having a nice visit. Slightly emboldened by the promiscuity of the past days, I quipped, “Last day here, but it looks like I’ll spend the evening alone.” I wasn’t sure if I was just a little horny and hoping to have some female company or feeling sorry for myself that I didn’t try and score at a club.
The clerk said, “Oh, so you’ll be leaving us tomorrow? What room number? I’ll see that a copy of your bill is slipped under your door before morning.”
Giving her my room number, I thanked her and bid good night. For a brief moment, my heart had jumped when she asked for my room number thinking she might be interested in providing some company. When she promised a bill, my heart sank back down immediately. I headed to my room resigned to the probability any action this evening would likely need to be self-administered. I was a little anxious to see the bill. It was going to be the second half of the embarrassment of Bob.