Some Cream With That? - Session 11

I was met by Cindy and Diana and Vickie this time in the bedroom setup. Since Vickie is a sex surrogate,the team of Cindy and Diana would not be present for this part of the session, perhaps something about liability? They would assist in the clean-out and getting things set, but then it was one on one with Vickie because I would have some form of sex with her. She's got a great face and body; she has a very appealing vibe about her too. She wore a full mask once we began and the cameras rolled.

They cleaned me out 4 times and they cleaned out Vickie 4 times too in the adjoining room. I got my privacy while evacuating.

They dimmed the lights a bit and we were alone. Vickie noted "You will follow my every command and you will stop when I say STOP." If at any time you can't take it just say "STOP." For items that you will not do or that you must stop for, there will be a penalty to pay and, in the end, the same thing is going to happen.

Vickie asked me to explain why a man should cleanup and I noted that my wife (lover) did cleanup and wanted me to have the same responsibilities and duties as her and that she also wanted me to experience the aggressive, demeaning way that most women learn about that and then accept their submission. I agreed with her and needed to work on letting go and having fair and equitable duties.

Because Vickie knew my likes and dislikes and my skills and needed skills, she set in motion some normal sex first to relax me. She sat in a chair and had me lick her to orgasm while I was kneeling on the floor. She had me lick her ass deep and for about 10 minutes.

I have always liked giving anal sex and fucking a woman in the ass. The nerve endings on fire, the woman trying to wiggle away, but also saying please do this, please keep going... Looking down and seeing my cock go in and out of that tight hole is such a turn on. The MOST manly that I have ever felt in my life is that conquest and on perhaps 4-5 occasions it was the best orgasm ever. Of course, Vickie knew all of that.

I lubed her ass and she let my fingers in. One finger, then to, then three and I went around and around to open it up. She was going to let me in there. She was going to let me be a man and feel like a man.

But there was a price to pay as I was about to find out. She reached into her bag and pulled out a plastic tub of cleaned and prepared strawberries that were 1" to 11/4" in diameter and removed the lid. She put them besides her, within my reach, and she said, "Time to play with some food." I was immediately intrigued and curious and turned on too. Vickie asked me if I wanted to play with them down there and I said sure. Strawberry-pussy sounded like fun.

I took one of the larger ones and admired how nice it was and reached down towards her pussy with it. She giggled and said, "Wrong hole" and then she handed me the lube from besides her. The old saying about "When in Rome" came to mind and I pulled her ass cheeks apart to inspect what I had been fingering and lubed the hole and strawberry. I wiggled it in so slowly and then pressed my finger in the hole until it was free. Vickie said, "one more" and I grabbed another and repeated the insertion process.

"Lick the hole" she said, and I did, it was fun. She then said, "Time to retrieve them" and I was not sure how. I reached in and that was not going to work, I could feel them and turn them to get the tip pointed out, but not get them out. She asked me to "Put your lips on it and tongue in the hole" and I went for that, on the floor on my knees with her ass over the end of the bed and I believe she pushed out as if having a bowel movement push and one of the strawberries popped into my mouth... She said "Let me see, let me see" with some excitement and I came over near her head and she saw it in my front teeth. "Chew and swallow" she said. I did as instruct and said, "Thank you, more please." She responded with that same enthusiasm, "Go and get it" and indeed I did just that. I showed it to her in my front teeth and then chewed and swallowed it again and repeated "Thank you and more please."

She said it was time for me to feel like a man. Obviously, she knew my whole profile from reading the interviews. I had to use a condom and that was fine with me. I entered her anus slowly and with care. I have always been gentle, and I walked her through the squeeze and let go process and took it slow. The problem with anal sex is that it is hollow in there; the rectum is empty and offers no stimulation.

The trick it to keep the tip of the penis in the rectum near the inner sphincter so that it stimulates the head of the penis. Either short strokes in that spot or long in and out all the way style to keep the cock hard using the sphincters. I prefer the long method and I went at it after about 2 minutes, and I knew she was OK. I asked permission to cum, and she said, "YES but there is a price to pay" and she said "Harder" to make me cum hard and for me to know she was into it. I looked down at her on her knees, my cock in that hole and it was glorious. I came hard, it was visually perfect, it was so nice, and she masturbated and came with it too.

After I calmed down for about 30 seconds or so she started to roll and said, "roll with me" and I was on the bed with my cock still in her, it was softening. I said, "Thank you" and she said, "Your welcome." She continued to roll off of me and the cock came out and then it happened. She lowered her ass over my face with her arms and face facing my cock and sat, her anus in my face and she said, "Lick it" and I did. She removed the condom from my shrinking shaft and rolled off me and then inserted the opened end of the condom into her ass and got on her tummy. She told me to empty the contents into her ass... She said, "All of it in me and be sure to get every drop in there, use your fingers to slide it in too, every possible drop."

With that task done, she slid the plastic tub of strawberries at me and said to "Insert two of them." I knew what the scene was now, I did as instruct and I was not looking forward to it, but it was sort of cool too.

She then ordered me to get on my back and I complied, and she once again mounted my face and placed her anus where I could lick it. "Now" she said, "Clean it out with your tongue and I want every drop cleaned up, I want you to consume both strawberries too. Get to work." Again, my brain was doing the "OMG" thing and I didn't want to, the hormones had dropped, but there it was, and punishments could be worse. This was my worst-case cleanup scene, my most NO cleanup possible scene. I just did it, I went at it like a wild-child and did as I was told. Plop into my moth with the first strawberry and cum... plop the second with cum... then the dripping cum that remained. I kept at it for about five minutes, and she moved forward and said, "It should be cleaned out now, good boy. "

Vickie said You hesitated at first and you know that means corrective action." I knew this could happen, she sat down on my face again, this time with her pussy lips and I licked and licked and then it happened... She said, "Not one spilled drop is allowed" and relieved her bladder into my mouth and as she did so she repeatedly said, "Not one spilled drop or we do these three more times." It was a flood of warm pee; I had no choice at all.

I have enjoyed licking women my whole sexually active life. I enjoy licking a woman while she pees (shower or toilet), but I don't ever and have never-ever swallowed. And here I was being defecated onto with a golden shower to swallow. It was a bit sour and rough to do, it lasted longer than I wanted, it was punishment and fortunately, I did not spill a drop. My wife (mistress) had wanted me to take her pee on several occasions and thought it would be a good punishment scenario and I was just "NO" about it. Here I was with a virtual stranger and it happened. I delivered a loud "Thank you and more please."

We showered together and Vickie made a quick text message to Dr. Marcus and the team came in as we were getting dressed.

In a strange scene to me, Vickie then described all the things that we had just done in clinical factual detail. It was humiliating to hear her describe me cleaning her, eating the strawberries covered in semen from her anus, swallowing the pee directly from her urethra placed upon my lips, etc. The team made notes and then asked about my feelings and ease of doing these things and I said my usual "Humiliated to have that all said aloud about me" and I added "not as difficult or scary as I had anticipated before these sessions started.

Perhaps the word 'doable" is in my mind set." I noted that the anal cleanup was the most absolute "NO" item in my mind, and it happened, and it was not terrible. The pee was a bit harsh and not fun, but I understood the concept of why.

I received the written instructions to edge 4-5 times and not cum each day until the next session. To practice my oral gag reflex stuff and to try to clean up my fingers if I did any play. The instructions encouraged me to touch my toes and stretch and hold that position for as long as I could in practice for the next session. And of course, it noted to accept this as normal, don't fight it, let it happen.