Chapter 10: New skills

Mary acquires new skills.

On Monday afternoon, a text message arrived on Mary’s dating app account from Matthew: “Hi Molly, I wanted to propose something to you.”

Molly wrote, “Hi Matt, tell me.”

“How would you like me to teach you how to deepthroat? With a girlfriend I had a while back, we learned how to eliminate the gag reflex, and then I’ve practiced it with some girlfriends I’ve had, and they’ve learned. You’ll be able to swallow all of my cock and Buck’s when he can. I assure you, it is one of the best sensations a man can experience, and something a woman can be proud of when she is able to do it.”

Molly asked me, “What do you think? I don’t know if I can do it. When your cock, or Matt’s, reaches the entrance to my throat, I gag and retch. On the other hand, I’d like to be able to do it. I can imagine the look on your face if I swallowed your cock whole.”

I replied, “I can imagine it, and my cock tries to get really hard inside the cock cage just thinking about it. The truth is, I’d love it if you could do it. But you decide.”

Mary replied to me, “I think I’m going to try.”

And she wrote to Matthew, “Okay. I’ll give it a try. What do you need to do?”

Matthew: “You need a long, flexible dildo. A rigid vibrator won’t do.”

Mary: “I don’t have one; we’ll have to buy one.”

Matthew: “And we’ll have to connect daily on a call to practice.”

Mary: “Okay.”

Matthew: “If you agree, every day at 10:00 p.m., starting today if you can get the dildo.”

Mary: “Okay. We’ll go buy it, and we’ll start tonight.”

Matthew: “Great. See you tonight.”

Mary: “Bye.”

Mary looked at me and said, “Well, a new thing for us to enjoy more.”

“Yeah,” I replied, “I’d love to.”

“Shall we go shopping at the shop where we first shopped?” “Perfect!”

We took the car and drove to the shop where we had bought the starter kit. We parked up and headed for the entrance with a determined step. This time, we were not so clueless; we were looking for something specific. Even so, when we got to the shelves, we were again a bit hesitant about the huge variety. Finally, we opted for a silicone one that was flexible, quite long, and of a thickness similar to my erect cock. It had the shape of a cock, with a head, grooves and ridges, veins, and testicles at the base. We commented that, even if it was very long, Mary didn’t have to swallow it all.

We paid the shop assistant, who was not the same girl as the first time, and returned home.

That night, we lay in bed naked and waited for Matthew’s connection through the dating app until he finally called. “Hi Molly, all set?” said Matthew, addressing only Mary, as usual.

“Hi Matt, all set.”

“The first thing you need to do is prepare some electrical tape. Then you have to put the dildo in your mouth as far as you can until it makes you gag. Then you hold the dildo with your fingers against your lips, pull it out, and wrap the tape around the dildo at that point where your fingers are.”

Mary did as Matthew instructed. She pushed the dildo in until she started coughing and gagging and marked that position with tape.

Then she replied to Matthew, “I’ve already done it.”

“Good. The technique is as follows: Every day, in the session that we’ll have, you insert the dildo until your lips are around the tape. You hold it in for a few seconds, longer each day, and pull it out. After a few seconds, you put it back in, hold it for a few seconds, and pull it out. The next day, you add another round of the tape after the previous one, further away from the tip of the dildo, and you remove the previous day’s tape and repeat the exercises again. So, each day, the tape is further away from the tip, and you insert a little more of the dildo and hold it for a little longer. Slowly, your throat gets used to it, and your gagging reflex disappears.”

“I see how it works,” Mary replied.

“But there’s more,” Matthew added. “To ease the discomfort and to distract attention away from your head, meanwhile, your pussy also has to be ‘active’. You can use your fingers to masturbate, use a vibrator, or you can even ask your husband to use his tongue since his cock is not ‘available’,” he said jokingly. “Whatever you prefer and whatever gives you the most pleasure. The goal is for you to be aroused and come at the end of the session, so that the excitement of finishing helps your body get used to having something in your throat.”

“I’ll enjoy it more with Buck, and that way, in addition, he gets to participate as well.”

“As you prefer. I’ll be happy to have Buck help you get ready to swallow my whole cock this Friday. Whenever you’d like, we’ll get started. The best thing to do is to start fondling and getting horny, and let me know when you want to start swallowing the dildo. I’ll mark the times for you.”

I kept thinking about Matthew’s words. I was going to help Mary deep-throat Matthew, to learn how she could better satisfy another man. On the other hand, I thought that, once we learned, we would both enjoy it. As Mary said, it had to be seen as a trainer. Besides, I would enjoy Mary’s body and making her orgasm. Trying to put all thoughts out of my head, I turned to caressing Mary’s body.

However, as I kissed her, I kept thinking that those juicy, fleshy lips that were pressed against my own lips would be around Matthew’s cock on Friday, and if the training worked, probably pressed against his pubis. And that tongue entering my mouth would be licking his cock and possibly his testicles when she took his cock all the way down her throat. These images made me uneasy, envious, and excited at the same time.

Again, I tried to push them aside and simply focus on the physical sensations that the contact with Mary’s lovely body gave me.

With my body on top of hers and my knees on either side of her body, I caressed her soft breasts as I kissed her. She caressed my chest, neck, and shoulders. My arousal increased, causing the inevitable attempt at expansion and erection of my cock. As usual, the cock cage cut it radically short and caused me discomfort, pain, and twisted excitement at having to wait until the weekend before I could get a full erection and enter Mary’s warm pussy.

Gradually, my mouth descended to her breasts, and my tongue played with her nipples. I nibbled on them and, sucking them, pulled them until they slipped from my lips, eliciting moans of pleasure from Mary. After a while, I continued my journey to her sex. I teased her by running my tongue up the inside of her thighs and down the hollows of her groin, between her thighs and her labia, until she desperately grabbed my head with her hands and guided it until my mouth was on her clitoris.

I pulled my head away and playfully said, “Weren’t you going to practice with your mouth and the dildo? You’ll have to earn your orgasm.”

“You’re too good with your mouth, and you turn me on so much, but you’re right,” she replied, and then, taking the dildo, she said to Matthew, “‘Whenever you’re ready. I’m ready.”

“Okay,” Matthew replied. “Start sucking and getting the dildo nice and wet. Imagine it’s my cock.”

Mary got on with it, toying with the dildo between her lips and licking it all the way around with relish. I watched her from my position between her legs and was sure that, as well as enjoying herself, she was doing it to tease me. Although I thought it was no longer possible, the pressure in the cock cage increased even more as I imagined her lips playing with my cock.

Then Matthew said, “Now put the dildo in slowly until your lips are around the tape and hold it there until I finish counting: 5, 4, 3, 2, 1. You can take it out now.”

I heard Mary gag, but because she had it for such a short time, she didn’t cough.

After a few seconds, Matthew repeated the sequence, “Put it in again: 5, 4, 3, 2, 1, that’s it. If you stick your tongue out at the same time, as if you were trying to lick the whole shaft from underneath, you open up the hole in your throat, and the passage is easier. You can also lick the shaft from underneath, and the man you do it to will go crazy. Let’s try it again: 5, 4, 3, 2, 1. You can pull it out.”

I watched Mary do it, and when she removed the dildo from her mouth, I slowly licked her pussy to relax her. My hands, meanwhile, caressed her belly, hips, and breasts.

It went on like this for a while. After several attempts, Matthew’s countdown started at 6, and, after several times counting down from 6, it started at 7.

Mary gagged less and less, but it was obviously uncomfortable, and, after a while, she said, “My mouth and throat are tired. Let’s stop now.”

“All right,” Matthew replied. “Tomorrow we’ll pick it up again. When you clean the dildo, remember to put a tape next to the current one, a little further away from the tip of the dildo, and remove the old tape.”

“I will do that,” Mary replied.

“Till tomorrow at the same time.”

“Till tomorrow.”

Mary cut the communication on the app, looked at me, and said, smiling, “Well, we had something to finish, didn’t we?” “Yes,” I replied.

I started to lick her clitoris without any restraint. She immediately closed her legs tightly around my head, and before long, even muffled by her thighs, I heard her moan and gasp loudly.

I continued to lick her, my chin soaked by the fluids gushing from her vagina, and after a short time, she squeezed my head more tightly with her hands and thighs, gave a guttural scream, and climaxed.

She stayed still and gradually loosened her grip on me, fortunately, because I was beginning to fear that I might suffocate. However, my rest was short-lived; after a minute or so, her hands again guided my head, which was resting on her thigh, to her sex. I began to lick her again delicately, this time starting at the opening of her vagina and slowly moving up to touch her clitoris. The taste of her vaginal fluids was sweet and fruity, and I spread it across her lips as I flicked my tongue. Her breathing quickened, and she began to stroke my hair with her fingers, this time gently, as if savouring the sensations after the initial rush and release.

I continued for a while, during which she reached several orgasms. Finally, she guided my head to hers with her hands until our bodies were facing each other and kissed me, soft and intense at the same time. She licked my jaw, soaked in her fluids, and kissed me again passionately. Then she looked intensely into my eyes and said, “I love you more than anything.”

I don’t know how I didn’t melt with emotion at that moment. I kissed her back, and we stayed in each other’s arms.

My excitement and desperation for an orgasm gradually gave way to a feeling of warmth and tenderness. During the week, we met online again for Mary to practice with the dildo. Each day, she managed to hold it longer and insert it deeper. We followed the same sequence: we would play and caress each other for a while, then Mary would practice with the dildo according to Matthew’s instructions, and then I would make her reach several orgasms.

By Thursday, she had gotten rid of her gag reflex and could put the dildo all the way down her throat, although it still made her gag a little.

When the session with Matthew was over and we were relaxed, she said to me, “I’m so glad I did it. I can’t wait to deep-throat you and make you cum in my throat. I’m sure you’re going to love it.”

“Yeah, I keep thinking about it. Besides, watching you every day—how you play with the dildo, how you suck it and lick it—turns me on so much.”

“Well, tomorrow you will be able to enjoy it.”

The next day, like the previous Fridays, we disguised ourselves as Molly and Buck and headed to the motel, where we had arranged to meet again.

After parking, we made our way to the room Matthew had indicated, which was the same as the previous times. Apparently Matthew knew the owner, and he always gave him the same one.

When we walked in, Matthew was already there. He greeted us, saying, “Hi Molly, Hi Buck,” walked over to Mary, hugged her tightly, and began kissing her eagerly as he ran his hands over her ass and breasts.

I stood there, looking at them. After a few seconds, he looked at me and, pointing to the closet, said, “I’ve already prepared your bed in there. Close the door so that we have privacy. You will be able to see through the slats in the door.”

Although I didn’t like his domineering tone, it was what we had agreed to as a condition, so I went into the closet, sat on the bed, and closed the door.

They continued to hug and fondle each other until Matthew said, “Molly, I can’t wait any longer to try out your new skill. Let’s get naked.”

They both undressed, leaving their clothes on the table, and then Matthew guided Mary until they were both in front of the dressing room, where I could see them through the slats, barely half a metre away from me. Matthew was on the left, and Mary was on the right.

Matthew put his hands on Mary’s shoulders and pushed her down until she was on her knees on the floor, his partially erect cock in front of her face.

She took his cock in her hand and began to run her tongue along the tip, licking it slowly and running her tongue all around it, like licking ice cream. Slowly, she began to lick down the shaft, running her wet tongue all over the surface, until the whole cock was erect and glistening with her saliva.

Then she opened her mouth and slowly rested her fleshy lips on the head of his cock. She lowered her head and gradually pushed his cock in until it reached the entrance to her throat. Then she stopped and moved her head back up until she had the tip of his cock between her lips, then lowered it back down and pushed it back into the same spot. After doing this a few times, she started to lower her head a little more each time, inserting more of the length of the cock.

The first few times I could see her gagging and choking, but she controlled it and gradually pushed more and more of the cock down her throat. As she had practised, she would stick out her tongue to facilitate penetration. She worked her way down the length of his shaft, withdrawing until she had only her lips around the tip of his cock, and down closer and closer to his pubis.