The Benefits of a Girlfriend Ch. 07

"Ew, not with your prick, silly boy. With your finger."

"Is that allowed with the pussy free thing? And what about Adam? You made the inside of your pussy his property."

"Just say you don't want to feel it already," she laughed.

"No, I didn't mean that!" I pleaded.

"I know," she smiled. "Let's not overcomplicate this pussyfree thing. If your pecker is pussyfree, you are pussyfree. And I'm sure Adam doesn't care if I let you feel me with your finger every so often. I only let you do it to remind you of what Adam's cock gets to feel and your prick never will. Don't you think Adam would appreciate me rubbing that into your face?"

"I do."

"Okay, then get on your knees and flip yourself off."

I did as instructed and she put my middle finger inside her just like before. After a dozen or so pumps where she clamped her pussy around my middle finger, she withdrew my hand. Then she walked over to the dresser, took out something, and hid it behind her back.

She walked back over to me and said, "These past two months, you've made my pussy very happy by wearing your sissy tube and abstaining from both masturbation and orgasms. I was wondering, do you think the combined feminine energy of the yin and the sissy tube has helped ease your masculine urges, like ejaculating and such?"

"I haven't really thought about it, but maybe," I replied.

"I think the feminine energy definitely made you more docile and submissive. I think that's partly why you were so eager for me to make you pussyfree. How would you feel about going ejaculation free as well?"

I wasn't sure "eager" was the right word, but I certainly enjoyed the erotic humiliation I received from being designated as permanently pussyfree. But, I surely wasn't ready to give up ejaculating, so I disagreed, "'I don't think I'd like that at all. I really need to cum."

"I see. So you still have masculine urges," she frowned. "Then, I bet after two months you're dying for a release right now."

"I am," I confessed.

"Okay, you've earned the opportunity for an orgasm. And I'm going to give you the choice of how that happens. Sound good?"

I smiled and nodded rapidly.

"The first option will be in the sixty-nine position. You can eat my pussy while I smack and punch your balls. If you can make me cum three times with your tongue, we'll go into the bathroom, remove your sissy tube and you can cum like a loser. How's that sound?"

"It sounds fun!" I answered.

"For the other option, instead of eating my pussy, you will eat my butt." Then she showed me what was behind her back. It was the anal starter dong the same length and girth as my stiff prick we had purchased on clearance back when we purchased the dildo called "Adam's cock". Putting it in my face, she asked, "Remember this."

"Yes," I replied extremely excited at the thought of putting it in her virgin ass. "You said we could use it for anal play."

"That's right," she giggled. "And, if you choose option two, we will do that tonight."

"Oh, then I want option two!" I replied. "I would love to lick your ass and then put this inside you."

"Oh no, you're not putting that in MY butt! I want the first thing entering me to be attached to a man. Maybe a finger or two first and then his cock."

"His cock?" I frowned. "I guess that leaves my prick out of contention."

"Oh, I did say cock," she giggled. "But, really, do you think your prick deserves that honor, Michael?"

"I feel like you want me to say no."

"I asked you a question. Unless I tell you what to say or I've already told you what to say, then I want you to answer honestly. This is an important subject and your thoughts about it matter a lot to me. Do you still believe you deserve to be the guy who takes my anal virginity?"

Second-guessing my urges, I answered, "I don't know."

"Okay. If you don't know, then you don't. That's settled. I'll find a guy who thinks he deserves it."

"Wait," I pleaded. "I do. I deserve it."

"Well, okay, then. But if we do this, you'll have to wear two condoms. And it will only happen for about a month or so until I'm ready to take Adam. Once Adam takes me bareback, all my holes will belong to him. And you will never penetrate anyone ever again. Deal?"

Eager for that "one last time" she didn't allow me to experience with her pussy, I agreed, "Deal. Are we going to do it tonight?"

"Oh no," she laughed. "You're going to have to spend a lot of time eating my ass and getting me used to the idea of being penetrated before that happens. I was thinking your birthday would be perfect. And if you want it to happen, you'll have to keep the sissy tube firmly in place until that day."

My birthday wasn't until the second week of October, so I was very confused, "So, that's option two? I just lick your butt tonight? No anal play? No cumming?"

"Option two means licking my butt tonight and eventually taking my anal virginity. And, also tonight instead of cumming like a loser, you can cum like a sissy when I take YOUR anal virginity with this," she explained waving the anal starter dong.

I was stunned. Option one was to eat her pussy, have my balls beat, and then masturbate and cum in the toilet. Option two was eating her ass, getting pegged and possibly cumming from prostate stimulation, and then penetrating her virgin ass in six weeks.

While agonizing over the decision, I glanced over and saw the brown bag on the bed. Hoping more information might help, I pointed and asked, "What's in the bag?"

She pulled out two identical familiar-looking dildo packages with the words "Adams cock" on them. "These were on clearance. They were the last two in the store and they were only forty-five dollars. I figured it wouldn't hurt to have spares. It's better for our relationship if we always have access to "Adam's cock" to satisfy me. Wouldn't you agree?"

"Yes."

Next, she pulled out a box containing an item I was unfamiliar with. She announced, "This is an enema bulb. It will flush out your butt-hole to help prevent any messes."

I looked up at her, rather stoically.

Last, she pulled out a three-pack of different size butt plugs. "These slowly stretch and open up your anus so the dildo will slide in with ease." She set the package on the bed. "So what will it be? Option one or option two?"

I realized it really wasn't a choice after all. She had put thought, time, money, and effort into one of the options and almost nothing into the other. I knew which option she wanted me to choose.

After I showered, Kristy filled the enema bulb with a mixture of warm water, baby wash, and baby oil. Then she lubricated the tip, inserted it into my hole, and emptied the contents inside my colon. To my surprise, it was rather pleasant.

Before leaving the bathroom, she told me to hold it in as long as I could, then go ahead and let it out into the toilet bowl. We repeated this process three more times.

Then she lubricated and inserted the smallest butt plug inside me, pulled it out, pushed it back in, and proceeded to fuck me with it for a minute. Then she did the same with the middle-size butt plug.

The largest butt plug, similar in diameter to the anal starter dong, met with a bit more resistance from my hole. Kristy persisted, applying more lube and pressing it firmly until it popped in causing me about ten seconds of sharp pain.

I next half hour was spent with her bent over the bed, in the doggy style position, laying on her back with her legs and ass up in the air, laying on her stomach, sitting on my face, and squatting over my mouth. Obviously, we weren't fucking. Instead, I was exploring her ass with my tongue.

About a minute into that final squatting position, she hopped off of me and rushed out of the room. I just stayed there blissfully awaiting her return.

When she did, she just came to the door and told me to follow her to the bathroom. When I got there, I couldn't help but gag from the stench. Kristy ALWAYS sprayed air freshener. I assumed she just forgot.

Kristy just ignored my reaction. She tugged on the butt plug and it eventually popped out. She inspected it before setting it down and flushing me out once more with the enema bulb. This time she had me release it with her still in the room. After I stood up, she looked to make sure we were still good to go. Then she reinserted the plug and led me back to the bedroom.

Once there, she had me get on my knees while she affixed the anal starter dong to the strap-on harness and then to her pelvis.

She stepped forward sticking the dong in my face and yelled, "Suck my dick, bitch!"

I jumped and froze.

"Do it now you little sissy bitch! Suck my dick!" she yelled even louder.

Fearing the neighbors would hear her, I obeyed, orally worshiping the piece of plastic the way I had seen Kristy pleasing Adam.

Kristy giggled, "Ooh, I like seeing you do that. And you're so good at it too! Since my mouth is just for Adam, maybe I should invite some guys over to use yours!"

I withdrew and pleaded, "Please don't."

She grabbed me by the ears and jammed the dong into my mouth, thrusting in and out with her hips and slapping the hard testes against my chin as she berated me, "Nobody gave you permission to speak you little bitch. Or to take this dick out of your mouth you ungrateful sissy cunt."

After a minute she started laughing and withdrew, "That was fun!"

I might have agreed if my nose, chin, and cheeks weren't so sore from being so roughly face fucked.

"Okay," she pointed. "Up on the bed. Lay on your back with your little fuck hole hanging off the side and spread those legs nice and wide for me."

Then she applied lube to my hole, took out the butt plug, and quickly stuffed it back in. She fucked me like that steady for about a minute.

The last time she withdrew the plug, she almost seamlessly replaced it with the anal starter dong. It was longer and not tapered like the butt plug, so it filled me up considerably more.

I honestly enjoyed it when she started to thrust in and out of me. Pinching my nipples every so often, she really seemed to be enjoying it as well. After about 5 minutes of steady thrusting, she asked, "Are you getting ready to come yet?"

"I don't think so," I replied.

She asked again every five minutes. The fifth time she asked, she stopped moving, looking disappointed and defeated. Then she raised her eyebrows and appeared to smile before turning and walking back to her dresser. With her back turned to me, she did something over there for a few minutes.

When she returned I saw that she had replaced the starter dong with the original "Adam's cock" dildo we had purchased. About five minutes and an ample amount of lube later, I was literally cumming on Adam's cock.

Semen was oozing from my limp prick, through the opening of my sissy tube, over my balls, and onto the dildo while Kristy was joyously still thrusting into me. I was having an orgasm without ejaculating.

Back in early August, like she often did during our telephone conversations, Kristy summarized some online lifestyle reading she had done, "So, I was reading about pegging today. Did you know a guy can orgasm from getting fucked in the butt?"

"I've heard of women having an orgasm during anal from pressure on the vaginal walls. Not sure how that would work for a guy," I replied.

"It's actually easier for a guy. Women have a g spot in their pussies a few inches in on the front wall. Guys have a g spot in their butts a few inches in on the front wall."

I laughed, "You almost had me, there!"

"I'm serious, Michael. Have you ever heard of the prostate?"

"Yesss," I played along. "It makes the jizz. The balls make the sperm and it makes the rest."

"Yes, and what do you think happens when you massage the prostate through the anus?"

"You cum?"

"They call it milking. It's an orgasm without ejaculation. Dribbling not spurting, you know."

I didn't know then, but I did now.

Laying there in post-orgasmic bliss snuggling with her, I thought about what had just occurred. The tool identical in size to my own couldn't effectively stimulate my prostate, but the tool the size of Adam's did the job in a mere fraction of the time.

And I realized what was true for my "g spot" was most likely also true for Kristy's g spot. And for that matter, every woman's g spot. She had proven to me that my manhood was completely useless for giving orgasms through sexual penetration. From that moment forward, I would never again be able to think of myself as a real man sexually. And I was okay with that.