Pleasuring Virginia Pt. 03

This story immediately follows Pleasuring Virginia (Part 2)

Virginia and I continued to share wonderful erotic adventures together. I always enjoyed pleasuring her enormous breasts and tasty pussy. It just kept getting better as we got to know each other. Most of our times together, she would have me suckle her breasts for a long time and then have me lick her pussy until she exploded. I always remained fully clothed and was never allowed to take my pleasure. I would always masturbate afterwards thinking about our last time together. She was always in control and I knew that if I wanted something different then it would be over between us. She made it clear that this was ONLY about her pleasure and that my pleasure did not concern her.

Less often, she wanted it not to be Virginia and Dave, but some role playing. Those adventures would always include a hard spanking. The only time I was allowed to be naked was when I was in the shower to be cleaned. These times would always include lots of breast suckling and end with my licking her pussy to orgasm. More and more often, she would orgasm by sitting on my face. Actually, it was more often standing over my face, since at age 75 she was not as flexible as she used to be. She arranged her bed such that I would lay my head off of the end of the mattress. She would stand over me and ride my face until she was completely pleasured.

I was good with our relationship. It felt right, and it was adding something else delightful in my life. Also, my sex life with my wife became much better. I was so horny that we fucked much more often than previously. I did have to learn how to hide my bruised ass when I was punished. Sometimes I wondered if my wife suspected that something else was going on.

Then Virginia mentioned her good friend Alice.

Virginia and Alice went way back. Alice became a widow several years ago. She recently expressed her growing sexual frustration to Virginia. Virginia told her about our relationship. Alice was intrigued and asked if I might be available to pleasure her. Virginia said she thought about it and initially did not want to share. Eventually she decided to give me the choice since Alice was so desperate, and she did owe Alice something special from some past adventures.

Virginia then described exactly what Alice wanted. Just like Virginia did before our previous erotic adventures together, she made it clear that my only choice was whether to accept it as it was, or decline it and move on. Alice is a Domme.

I said YES.

Virginia and I each had a rare open weekend coming up. My wife was going to a quilting convention out of town. Virginia's daughter and granddaughter were going to Disney World. She had the house to herself from Wednesday to Monday evening. She arranged for Alice to fly in Thursday and stay until Monday afternoon. I was told to knock on her door at 7 pm Friday night.

I was definitely nervous when I knocked on the door at the specified time. I had some experience a while ago with a pro Domme. It was not fulfilling. It seemed too programmed. It was like, one for column A and two from column B. She asked me what I wanted, and we did it. I got tied up and spanked. I wanted to try pegging since I watched porn about it. The pegging hurt more than it felt good. I know I have submissive tendencies, but I never let myself really go in that direction. I've thought about it and realized that I was definitely submissive to Virginia, but that was all about me pleasing her, and I really enjoy sucking breasts and licking pussy. It felt so real with Virginia, and somehow I thought that would translate to Alice. I don't know. Guess at the end, I did not want to disappoint Virginia and thought I would give real submission a try. Also, I saw a picture of Alice, and she is gorgeous.

I knocked on Virginia's door at the exact time she gave me. Virginia opened it and Alice was standing next to her. I was immediately smitten. Alice is a barely five foot tall, barely 100 pound gorgeous blond. Her body was tight. She wore her long blond hair straight back. She smelled fantastic. I was captivated by her scent of lavender and lilacs. She looked much younger than what I later to find out to be 72 years old. My jaw must have dropped as part of my reaction because Virginia immediately made a comment. "Virginia, one of the most satisfying parts of this is wiping away that male bullshit attitude forever. Wait until you see his demeanor when he eventually leaves us".

I somewhat gathered myself, and we made our way into the living room. Virginia poured me a glass of wine with a comment that it looked like I really needed it. And I did! Alice directed the conversation and immediately probed my sexual history, with an emphasis on my experience as a submissive. She was especially interested in my experience with a pro Domme. Virginia listened intently and took it all in. Alice made it clear that she is in charge and decides what feels most right to her. I was given safe words of red means stop, and yellow means slow down. Alice said that they are there to be used. Sparingly. Alice said it would disappoint her to slow or stop, but she will. Virginia made the point of adding that anything that would disappoint Alice does really disappoint her. I got the message. They asked again if I still wanted to continue. I did not hesitate to say YES. Alice confirmed that I had done all the preparation she told me through Virginia. She then got a glean in her beautiful light blue eyes.

She rose and told me to strip. I looked around in the living room and quickly did exactly what she told me to do. She rose and walked towards the back bedroom. She paused and turned around and told me to crawl after her. Virginia laughed as I scurried after Alice naked and crawling like a baby. We went to a guest bedroom where Alice was obviously staying. She pointed to the top of the unmade bed. There was only a white sheet on the bed. I saw the bedding all neatly piled in the corner. I crawled up to the bed. Alice told me to be face down on my elbows with my ass up in the air. She quickly tied my left hand to my left ankle and my right hand to my right ankle. A two-foot spreader bar was attached. There I was. Vulnerable and available.

I heard Alice describing her mindset and approach to Virginia. Virginia was watching intently. I now know Virginia well, and she was quite aroused. Alice described how she establishes control to have her sub understand that she is completely in charge. Being in charge is something Virginia and Alice both share. I felt something cool lubricate my asshole. Soon, a finger inside a rubber glove was inserted. It did not feel bad. YET! I just let me mind drift. Soon I felt some hard in my hole. My asshole did start to hurt as it was almost virgin. I heard Alice tell Virginia that my asshole will be well-trained and look a lot different at the end of our time together. Alice slapped my ass hard and said it was time to begin my ass training.

I heard a squeeze and felt the butt plug expand in my ass. Alice laughed when she heard my gasp. She said that I obviously needed a few more squeezes. I felt the plug grow and grow until it was uncomfortable. I moaned and shook myself. I heard Alice say that this was a good start. Alice then roughly grabbed my cock and balls. I felt something hard against the upper part of my legs. I heard Alice describe what a humbler does to a sub. It hurt as she pulled my cock and balls into the slot and clamped the two pieces together. I was even more vulnerable and available than before.

Alice untied my legs and ankles and removed the spreader bar. She told Virginia there was no need for them as I am now totally under her control. Alice told me to try moving. It did not go well and it hurt. I flopped onto my side and felt the hard wood against my upper legs and the pull on my cock and balls. I heard both ladies laugh at my predicament. Alice then placed me in a kneeling position on her bed. I heard her take something out of a bag and stand behind me. I really felt the first hit on my exposed cock from her small leather paddle. I cried out. Alice started to softly tap my cock with the paddle and build it up to increasingly harder and bigger hits. I was yelping and was captured by the sensation. A part of me knew I could call out a color to stop, but another part of me did not want to disappoint them, and I thought that I could take it. Alice then moved on to my balls, and that was even more difficult to take. She pounded it hard, but she somehow knew how much I could take. She took me right up to the yellow line and then paused. She caressed my cock and balls and told me how horny she is. She told me I that I will now pleasure her with my mouth and if it was not good enough, then we will repeat this punishment until I get it right.

I was much more than good enough. Alice removed her clothes and positioned herself at the top of the bed. It was even sexier knowing that Virginia was eagerly watching. I did not hesitate at all, but immediately stuck my tongue deep in her pussy and caught her erect clit between my upper lip and tongue. I firmly sucked and licked and heard her moans. It was spectacular. Alice was calling out that I was doing a great job and that she was so fucking horny. I lost track of time, and it seemed to go on forever until Alice exploded all over me. I eagerly lapped up everything that appeared in my mouth and lips. Alice grabbed my head and shook it back and forth. Eventually she pushed me off. I heard her ask Virginia if she was ready.

I saw Virginia standing next to us at the top of the bed. She looked more aroused than I've ever seen her. She lifted her sundress over her head. She removed her black silk panty. She took Alice's place. I eagerly licked and sucked and did everything possible to pleasure Virginia exactly as she desired. She attacked my face and held on to my head as she used my lips and tongue for her own pleasure. She immediately came hard and then kept me in place as she enjoyed several other orgasms. We both got exactly what we needed and wanted.