Chapter 12: Mary practices new skills

On Monday morning, I left for the office while Mary stayed at home to prepare some documents and prepare for meetings later in the day.

When I returned home in the afternoon, Mary said, “Matthew contacted me this morning to ask me how I liked my date with Thomas. I told him, ‘fine, although very intense, even too intense’. He laughed and told me he could imagine. He also asked me if I had ever experimented with anal sex. I told him no, that I disliked the idea, but Matthew encouraged me to try it. “Matthew sent me a reference to a female-oriented website by sexuality specialists (badgirlsbible.com) that some of his girlfriends had used that explained many aspects of sexuality, including facts about anal sex as well as techniques to provide more pleasure to the partner (orally, vaginally, or anally). I’ve been reading some of the articles on the website, and I really think I’d be tempted to try anal sex.”

“Are you sure?” I replied, “You thought it was painful and degrading.”

“Yes, but after reading about it, it seems that many women find it pleasurable. Some even reach orgasm that way too. I’m curious to try it.”

“I must confess to you that more than once I have fantasised about how much I would like to fuck you in the ass, but as you have once remarked that it was something you did not like, I had not dared to propose it to you.”

“How respectful you are, Charley, and how much I love you for it!”

“And now, imprisoned in this cage, I shall have no chance to try it.”

“Well, you shall have your chance next Friday.”

“But are you going to tell Matthew that you will try it?

“Yes,” Mary replied.

“But then he’ll say it’s something you’ve learned with him, and I can’t do it as long as we have these encounters, like he said about the deepthroat. He’ll be the first man to fuck your ass.”

“Well, actually, the first one in my ass will be the anal plug we bought in the kit, or even some more plugs, because it is convenient to use several of increasing sizes. I’ve read that it’s good to get used to and train your sphincter by keeping something in it before having anal sex. Also, as it happens the first few times you have vaginal sex, it can be a bit uncomfortable. I’ll get used to it with him, and then we can enjoy it together without discomfort. Don’t worry. Sometimes too much importance is placed on virginity.” And Mary added, with a smile, “It seems odd that I have to remind you of that, when I’m the one who was raised in a Catholic family.”

“You are right, Mary. As always, you analyse situations with great lucidity.” “I think for you men, virginity is almost more important than for women, as a way of ‘marking territory’, like wolves peeing to mark their hunting ground. But we women are not a territory; we are people.”

“Yeah, maybe that happens to us,” I replied thoughtfully, pondering what she had said.

“Well, I’ll tell Matthew I’ll give anal sex a try. And if it’s okay with you, we can go buy some anal plugs in a different size and lots of lube.”

“Okay.”

“And don’t worry. I adore you, and you are the first and only one in my heart. Let’s explore some more with Matthew, and then we’ll continue exploring on our own and practicing everything we’ve learned.”

Mary hugged me intensely, and as always, when she expressed her love for me, I felt very much at ease.

After texting Matthew that Mary had decided to try anal sex the following Friday, we went to the usual sex shop. We picked out two plugs slightly larger than the one we already had, a bottle of lube, and a kit to do an anal wash, somewhat less intrusive than a full enema.

Back home, we cooked a light supper, listened to music for a while, and then went to the bathroom. Mary undressed completely, applied the anal wash by inserting the cannula into her rectum and applying the water, and when she thought she was clean, we went to the bedroom. There, I undressed as well, and we lay down on the bed. Mary on her back and me on my side. Mary took the smaller anal plug, the first one we bought, applied lubrication, and placed it at the entrance to her anus, between her spread and bent legs. She pushed slowly, but made a face of discomfort.

She asked me to help her, so I kneeled between her legs, took the anal plug, and started to push slowly against the opening of her anus.

She said, “I’ve read that you should try to relax and push a little, like you’re sitting on the toilet. I’m going to try that. You push gently.”

I pushed the tip of the plug in a bit and pulled it out, played with it around her anus and around her perineum, and every now and then tried to push it back in. Also, in the position I was in, I had Mary’s wonderful pussy just inches from my face, so I gave it some licks.

Little by little, I noticed how her sphincter relaxed, and it became easier and easier to insert a little more of the plug. On the other hand, after more than a week locked in the cock cage, I was very excited, and my cock was as swollen as possible, which was very little, and it was tight against the rigid bars that enclosed it. I couldn’t help but wish I could have my cock free and insert it into the soft opening in front of me. For lack of anything better, I settled for licking her gently, running my tongue along the length of her vaginal lips, and fiddling with the tip of my tongue on her clitoris. Seeing her vagina so close now, I couldn’t help but remember how stretched it had been a few days ago, when Thomas had shoved his huge cock all the way in, deep inside Mary.

It seemed impossible that something so thick could have fit into that opening or that such a great length could fit all the way in. Surely, the elasticity and adaptability of a female vagina were unbelievable. The thought of it, and the thought that next Friday, after two weeks of chastity, I would be able to enjoy that delicious feeling inside her, made me even more aroused, causing me great discomfort in my testicles, due to the ring pulling on them, and in my cock, being bent downwards.

The pain made me lower my attempt at an erection, and, to avoid further agony, I turned my attention back to inserting the plug into Mary’s anus as gently as possible.

After several attempts, adding some lube, stroking and fiddling with her perineum, and occasionally licking her sex, I managed to insert the plug as far as the widest part of the plug without Mary complaining. Then, with a little pressure, the plug, helped by its shape, went all the way in until only the wide base was visible.

Then I asked Maru, “How does it feel?”

“It’s a strange sensation. It was uncomfortable at first as you tried to get it in, but as I relaxed, the discomfort lessened. Now it’s just a weird feeling.”

“I tried to make it as pleasant as possible.”

“And you succeeded,” Mary replied with a broad smile. “And I’d like you to keep making it pleasant.”

I needed no further prompting. I licked her pussy with relish, trying to concentrate only on her pleasure to keep my arousal from becoming painful.

Her vaginal fluids began to flow copiously, and I began to lick them off, pushing my tongue into her pussy and penetrating as deeply as I could. She had a soft, sweet taste that I had always loved.

“You’re fantastic with your tongue, Charley. My pussy is still a little sore from the session with Thomas, but you’re making it totally go away.”

Encouraged by her words, I continued to attack her sex with my tongue and lips.

She began to moan and gasp louder and louder, mumbling, “Yesssss ... Charley ... huummm ... yessssss ... oohhh ... huumm ... like this.”

Finally, she stiffened and climaxed. I lifted my head to enjoy watching her face of pleasure: her eyes closed, lips half-open, nostrils dilated, cheeks flushed, and lips swollen and red. It is always satisfying to watch your partner enjoy you and reach orgasm, whether it is with your mouth, your hand, or your cock.

After enjoying the ecstasy for a while, she gently guided my head with her hand to continue my efforts in her sex.

I continued until she reached several more orgasms.

Then I lay beside her, watching as her rapid breathing gradually slowed, how her chest rose and fell in rhythm with her breathing, how her soft breasts heaved, and how her hard nipples slowly relaxed. I brought my hand to her breast and ran it gently over the entire surface. Grasping and groping her breasts, I desperately wanted to make love to her but was unable to do so, conforming myself only to caressing her.

After a while, she fell asleep, exhausted, and I, after a long time, got my arousal out of my system and was able to fall asleep.

The next day, Mary got up, went to the bathroom, and removed the anal plug. It took her a while to remove it, but she told me she thought she would get used to it.

Over the next few days, every night we repeated the tasks. On Tuesday, we used the smaller plug again, and this time it was much easier for her to insert it. Mary had gotten used to relaxing her sphincter. She also read that you have to push slightly outwards, like when you are pooping, and that also helped.

On Wednesday, we used the middle plug, and on Thursday, we dared to try the bigger plug. As I pushed it in, I thought that the next night it would be Matthew’s cock that would be working its way through that tight channel. Matthew’s, not mine, would be the first cock to enjoy penetrating that opening. The first cock to ejaculate streams of cum into Mary’s rectum. And I was helping to make that happen. Although Mary had reasoned that it didn’t mean anything, something inside the most primitive areas of my brain made me feel uncomfortable. Why should he have this ‘privilege’? Wasn’t it mine as Mary’s husband?

On the other hand, Mary was right, and the more rational part of my brain admitted as much. Sex the first few times could be uncomfortable. Being the first at something didn’t give any ‘title to property’, nor was she a ‘property’. And I had had sex before I met Mary, and it didn’t dull or affect my love for her. However...

I tried to put all these ideas out of my mind and focus on the present moment. This last plug was the largest, and at its widest part, the diameter could be somewhere between that of my cock and Matthew’s, which was a little thicker. As on the previous days, by pushing gently and withdrawing a little, and thanks to Mary having learned to relax and ease its way in, I was able to insert the plug. It made her a little uncomfortable, but once fully inserted, she had no discomfort, except for the usual ‘weird feeling’, as she described it.

Like every day, once the anal plug was inserted, my mouth made Mary reach several orgasms.

On Friday, when we got home, as well as turning into Molly and Buck, this time we had additional tasks: applying the anal wash to Mary and, after applying lots of lube, inserting the larger anal plug, to prepare her for her first anal sex. We also took the lubricating gel with us to use at the motel. As we drove to the motel in the nearby town, it seemed to me that Mary was restless and fidgeting in the seat, so I asked her, “What are you worried about?”

“I don’t know if it will hurt or if I will like anal sex.”

“Well, you don’t have any commitment; if you don’t feel like it, just say so. I thought you were convinced.”

“So did I. But so far, it’s just been an erotic game between the two of us,” she replied. “And a very satisfying one at that,” she added with a big smile, and she grabbed my arm. “But it will be a real cock going into my ass, not an anal plug, and someone else’s, not yours,” he continued.

“You know that whatever you think is fine with me,” I replied.

“But on the other hand, after reading about it, I’d like to try it. Even more so after you told me that you’d fantasised about it once. I wish you could make that fantasy of yours come true.”

“Well, if we both want to try it, let’s try it. But if at any time you dislike it or it hurts, say so, and it won’t be continued. And Matthew will have to admit it.”

“Yeah, don’t worry about it.”

When we arrived at the motel, we made our way to the room booked by Matthew. After knocking on the door, a smiling Matthew opened it and greeted us. After stepping inside and closing the door, Matthew said to Mary, “Molly, two weeks since last time, I’ve been looking forward to your arrival.” He rushed over to her, wrapped his arms around her, and began kissing her.

After a while, she began to respond to him. I sometimes thought that it was strange that, as soon as they met, without prior conversation or waiting for a while, they both ‘got down to business’. But on the other hand, it was clear to both of them that this was not about friendship or love.

As Mary said, it was ‘an exercise’, ‘just sex’, and there was no point in pretending otherwise. Like when you get to a gym and start training without entertaining a chat. It was even about preventing it from evolving into another kind of feeling, so better not to talk too much. Besides, as Mary had told me, Matthew didn’t have a very bright head, so there weren’t many possible topics of conversation with him either. What he did have was stamina and a great body.

As usual, I went into the closet and sat there to watch.

Matthew and Mary were still cuddling, kissing, and caressing each other with increasing intensity and ardor. They both started to take off each other’s clothes, and when they were completely naked, they lay down on the bed. After last week’s encounter, I again had an erotic show in front of me, and I saw my wife’s beautiful naked body and her enjoying herself with another man. My cock was trying to get erect, with the usual maddening failure.

Matthew, lying on top, was passionately sucking on Mary’s right breasts while his hand was kneading her left one. She stroked his head and back and kept her eyes closed, enjoying the sensations. Soon, he moved between her legs, spread them apart with his hands, and placed his fully erect cock at the entrance to her pussy. He pushed slowly, but steadily, until he pushed his thick cock all the way into the depths of Mary’s vagina. When their pubes touched, she threw back her head, let out a little moan, and hugged Matthew’s strong shoulders.

She must have been well lubricated, as she didn’t seem to offer any resistance. Despite the orgasms I had given her with my mouth, the desire to feel a cock inside her, along with the caresses and foreplay, had been enough to make her vagina very wet.

Matthew withdrew his cock until only the head was inside Mary and then pushed it back in, a little faster, all the way in, eliciting another moan and shudder from Mary. He repeated his actions, faster and faster and harder and harder. Mary’s breasts swayed with his thrusts, and moans escaped from her mouth continuously.