A Lesson in Pegging
by Brookell
Copyright© 2021 by Brookell
“Erica, what’s bothering you?” Helen looked at her friend with some concern. She was rarely so distracted.
“It’s nothing,” she said after a moment.
“That’s crap and we both know it. Something is bugging the hell out of you. Can I help?”
“I don’t know, Helen, it’s Aaron. He’s been pushing me about something.”
“What?” Helen usually thought well of Aaron.
“Nothing, don’t sweat it.”
“Erica, just tell me. It might make you feel better and you know you can trust me!”
She looked at Helen like she was torn between telling her and keeping it private. But it really was bothering her. Maybe Helen had an idea how she can handle it? “He’s been after me about something.”
“Erica, do I need to pull teeth?”
She made a small smile at that. “He wants anal sex.”
“So, give it to him, he might like it?”
“Him! How can you say that! What about me?”
“You misunderstand me, Erica. I’m not saying to let him have your ass, take his.”
Erica looked very confused.
Helen smiled, “Come with me.” Helen led her to her bedroom. From a drawer, she pulled out a couple of sex toys and a harness. “So, give him what he wants and fuck him in the ass.”
Erica looked shocked partially at the idea and also at the words. She can’t remember the last time Helen said the word ‘fuck’. “I don’t think that’s what he wants,” she said with a slight stutter.
“Has he specifically said he wants your ass or just anal?”
Erica looked down slightly as she said, “Anal.”
“Perfect, just show him these and tell him you’re ready for anal. Ask him doggie or missionary.”
Erica looked speechless and then laughed, “Are you kidding?”
Helen grinned, “Look, Erica, more than likely he’ll shut the hell up and start worrying about his own ass, especially if he is sure you’re serious. If nothing else, think of the look on his face!”
Erica actually thought about it and laughed a little more. She was a bit annoyed about Aaron’s request. The fact he’s been pressuring her also made her uncomfortable. She wasn’t a prude but didn’t like being pushed.
“But what if he says yes?”
“Well, my advice would be to do it. That doesn’t mean you have to give him your ass.”
Erica shook her head in amazement, “Why do you even have all this stuff?”
It was Helen’s turn to look a little uncomfortable. She hadn’t planned on revealing much and the suggestion was just on the spur of the moment. She thought the tossed caution in the wind, after all, she trusted Erica. “Roger enjoys it.”
“Your husband? Roger likes...”
“Yes, Roger does enjoy it, as do I.”
“You like it ... there?”
Helen smiled at her wording, “Yes, in the butt! You know you might like it too.”
“I don’t think so.”
“Well, anyway, you can borrow the harness and my smallest toy. If nothing else, you might shake him up.”
“I don’t know, I’m not sure how to even use this?”
“Well, that’s easy enough to fix.” Helen stripped off her shorts, leaving her in her top and panties, and then she started putting on the harness. Erica stood there just looking like she wasn’t sure what to do.
Helen spoke as she arranged it. “There are several things you can use; I like the harness because it puts the base of the toy against me and I can orgasm while using it.” She pointed to a purple, odd-shaped one that she had also pulled out of her drawer. “That one can be used without a harness, you insert it in you and that keeps it in place. But it not always strong enough for anal and tends to come loose.” For a second, Helen thought she might have hinted at too much, but Erica seemed to still be in shock. She figured Erica would really freak out if she knew how Helen used that particular toy and on whom.
She took one of the toys and inserted it into the harness and tightened a couple of straps. “See, now I have a penis capable of fucking!”
Erica still hadn’t said anything.
“Here, touch it.” Helen took Erica’s hand and wrapped it around her dildo.
“See it feels real, doesn’t it?”
Helen felt her squeeze it then she pulled it off like the dildo was on fire.
“Don’t get squeamish about it, it’s clean.”
“How do you clean it?”
“When I just owned one, I used plain soap and water. With my collection here, I just load them in the dishwasher.”
Erica seemed to shake her head like the answer of something as normal as a dishwasher shouldn’t be part of this conversation.
“Now, if you want to do this right, you have to be firm with him. I won’t say not to take ‘no’ for an answer, but it really is only fun if it’s consensual. Don’t try and force him, but be firm and make sure he understands you are serious.”
“I’m not sure I can do this.”
Helen stood there for a moment looking at her friend. She knew she didn’t have a very forceful personality. She was one of the nicest people Helen knew. She took her hand and put it back on the toy and held it there.
“Just be firm. Make him understand that it’s something you want.”
Erica tried to pull her hand off, but Helen held it there.
“Firm!” She held her hand and started rubbing the toy with it.
In a moment, Erica was doing most of the rubbing. “There, you see. Be firm, not pushy. Make no demands, just be firm and guide.” Helen was almost surprised she was feeling a little turned on. She never imagined Erica like this, almost any of her other friends, but not sweet, kind Erica.
Helen turned Erica to face her and then sat on the edge of the bed. Erica’s hand never left the toy as she bent over. Helen guided her to her knees. “That’s it, just go with it.” There was a look on Erica’s face as she continued to stroke it, she was also looking very closely at it. It was an impressive toy, lifelike and almost ten inches long. “Spit on it.”
That broke the spell for a moment, Erica said, “What?”
“Spit on it. You’ll need the lubrication plus it looks really sexy all shiny.”
Erica paused and did as she was told. The glob of spit ran down the shaft and hit her hand. She then rubbed it in and had to agree with Helen, the off-pink color glistened from her spit and it also made it easier to stroke. There was an unfamiliar scent in the air as Helen touched the back of her head and gently pulled her even closer.
“To do this right, you want to not just fuck him, but you want to make love with him. Since you are in what you might call the controlling position, treat him as if he probably has treated you in the past. Do you remember the first time you sucked his cock? It was probably something like this.” The tip of the dildo touched Erica’s lips and she opened them.
Erica felt strange, but if she could speak, she would have disagreed with Helen on how the first time she sucked her husband off happened. They were in high school and were on a double date with Jake and Bev who were in the front seat while she and Aaron were in the back. She really hadn’t wanted to go up to park at the Point. She knew it was the favorite parking spot for couples. She sort of got outvoted. They weren’t there three minutes when Bev’s head disappeared below the front seat. Aaron seemed to expect the same sort of treatment after a bit of kissing, and while she was a bit reluctant, she went along. She didn’t like it much. It wasn’t until after they were married that she got used to it, it still wasn’t her favorite thing to do.
But this was different. Helen didn’t seem to expect her to do it, it felt more like she was giving her an opportunity. There was no pressure, no pulling, just a little guidance. It felt large in her mouth, larger than Aaron. It also didn’t have much of a taste, unlike his muskiness. She kept her hand around the base and sucked on that dildo like it was real.
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