Adam has been my wife’s friend since high school. He’s always been timid and a bit of a recluse that doesn’t know how to talk to girls, except for Brenda. It’s no secret that he had a crush on her for the longest time. Even though he knows Brenda and I are in an open relationship, she doesn’t want to be his first, as much as I’m sure he would like.

Yet over the years, we have had a few occasions where Adam has gotten lucky to get a glimpse of Brenda’s wild side. One time, he called while we were having sex and Brenda picked up. They talked as she tried to hide her moans until it got too hard and she just let him hear everything. Another time, she showed him a few pictures I’d taken of her in lingerie.

This year, Adam decided he wanted to get a girlfriend. He’s in his late twenties and has never had a serious relationship. In recent months, he has been hitting the gym and working on himself. The change is very noticeable, he’s lost weight and cleaned up well. Brenda helped him shop to find a style that suited him and she helped him create a dating profile. To his surprise, he began getting a few matches. After getting some texting tips from Brenda, he had managed to land a date. As she told me the news about his date, I couldn’t help to think he might ruin his chance due to his anxiety and awkwardness around women.

"How is he going to lose his fear of talking to women?" I asked.

“I know, he’s been so nervous. He keeps asking me to help him but I’m not sure how. He said he doesn’t know how to talk to them and even if the date goes well, he doesn’t know what to do.” she said. She had helped him get this far and didn’t wanna let him slip back to his old self due to some failed dates. After some silence, Brenda said she had some ideas and warned me that it might get a little wild.

We invited Adam over to our place. He had no idea what was about to happen. When he arrived, Brenda was in the shower. I chatted with him about his date. He was nervous but he told me how thankful he was to have a friend like Brenda. He explained how much he had been able to improve himself thanks to her and might actually have a shot at a girlfriend.

Brenda walked out of the bathroom wearing a towel, saying hi to us casually. I noticed Adam quickly turn his head away from her, either out of respect or fear.

"Adam? I said hi..", she said. "Hi" he replied, still looking away from her. "Look at me Adam.” She demanded. “Since your date is coming up, I figured we should prep you for it, if that’s okay with you. You sure need it.”

"P-prep me? Yeah that would be great, what are we going t-“ before he could finish his question, Brenda had dropped her towel to the floor, leaving both of us speechless. Brenda’s small, slender yet curvy Latina body took his breath away. He was visibly shaking.

"If your date goes well and you take her back to your place, you can’t have that scared look you have right now. You’re almost 30, you should know how to keep your cool when a girl takes her clothes off." She explained.

Adam nodded. She walked around her house casually, heating up some water to make tea. This allowed us to get a good look at her. His eyes were glued to Brenda’s body. He was seeing his first nude woman in person and it was his best friend’s. His face was red, and he couldn’t stop stuttering. He had known her for so long and had a crush on her for most of that time. It was a wet dream come true for him but he didn’t know how to react.

Brenda stopped what she was doing. “Come over here, I know you’re nervous and I don’t want you distracted for the next part.” Brenda said. “I’ll close my eyes, you can explore my body, get comfortable with it, just don’t take things too far.” He looked at me for approval. I nodded and replied “You heard the lady. Do as she says, before she changes her mind about helping you.”

Adam immediately went for her small, perky boobs. I’d caught him so many times staring at them when she didn’t wear a bra or showed cleavage. He squeezed them and played with her puffy nipples until they were hard. Then he kneeled down and touched her pussy. She moved her wide hips side to side reacting to his touch. He admired her pussy for a second before burying his face in it. He ate her out like he’d been starving. She tried to keep her wits but failed as she laughed and stepped back. “That’s enough of that.” She told him. “Sorry, I always wondered what it tasted like. It’s so soft and warm.” he said. He turned her around get a look at her ass. She spread her legs and bent over for him. He squeezed and slapped her ass for a minute or two. “Are you feeling more calm now?” She asked. “Definitely.” He said as he let out a big sigh.

They sat in the dining room and she began roleplaying as his date. She helped him find subjects to talk about and questions to ask. I gave them some space and headed to the living room. I figured Adam was nervous enough with Brenda being nude and I didn’t wanna make it worse. I could still see both of them.

After a while, he seemed to get it down, he was able to make small talk with Brenda as if she was any other girl, and better yet, maintain eye contact even though he could easily look down at her boobs.

"Alright, you got the small talk down, even some flirting. Now let’s practice kissing." Brenda said. They stood up and hugged, Brenda pressing her bare body against his. He wrapped his arms around her waist and leaned in for a kiss. They began making out, Brenda taking the lead. As they kissed, Adam’s hands moving down her back to her ass. She grabbed his head with both her arms and tongue kissed him.

“Not bad at all” Brenda said. They kept kissing as she told him some do’s and don’ts until he got it down. She asked him if he was okay with going further as she wanted to respect his boundaries with his virginity. I knew he would happily agree to anything she wanted to do to him but she wanted his first time to be special and with someone he could have a romantic relationship with.

She explained how he could learn the signs that a woman is enjoying something and how to properly ask for consent. She gave him a few more sex tips before putting them into practice.

“Now I’ll show you how to pleasure a woman.” She guided him towards the living room where I was and laid on the other side of the L shaped couch. “Do as you like and I’ll tell you if it feels good.” she said. Adam got on top of her and kissed her neck. Brenda used her hand to guide him softly to where it felt good. He kissed his way down to her boobs and began sucking on her nipples. Brenda moaned as she told him to keep going. She instructed him on how hard to suck or bite and how to use his tongue on them.

Adam moved down to her pussy and began fingering her. She stopped him and showed him how he should tease her first. She told him to run his fingers across her pussy lips until she was wet, then slowly push his finger inside. Then she explained how he could reach try to reach a girl’s G spot while fingering her. He began eating her out but was completely lost. She moved his head up to her clit and asked him to use his tongue on it.

With two fingers inside her, hitting her G spot and his tongue playing with her clit, he was becoming a pro. “Keep going, at that same pace.” She said. She began moaning louder and louder each time. I could tell she was getting close. Before she could cum, she stopped him.

“Alright that’s enough, I think you’re ready.” she said as she caught her breath. “But about me? What if I cum fast? That’s what I’m afraid of.” Adam replied.

Brenda looked at him for a few seconds and conceded. “Okay, pull your pants down.”

Adam did so quickly, revealing his hard cock. Brenda got up and sat next to him. “I’m just gonna give you hand job.” Adam tried to explain he was okay with taking it further so she could keep teaching him but she was dead set on this. She began stroking his cock slowly. Within seconds, Adam asked her to stop since he was about to cum. Brenda stopped and squeezed the tip of his cock until he told her it was safe to keep going.

Brenda got on the floor and kneeled between his open legs. She said she could see his face better and would be able to tell when to stop. She kept stroking him slowly, stopping when she could tell he was close so he could practice self control. After a few stops, he was able to last longer. She spit on the tip of his cock and began stroking him faster. She stopped again but it was too late. They stood still for a second or two before Adam whispered “fuck fuck fuck”. She tried covering his cock with her hand but cum shot through her fingers. He grabbed her head and pushed it down on his cock. Her lips covered the tip of his cock as she began sucking the cum out of him and swallowing it. He moaned loudly as his legs shook. Her lips and warm mouth must have felt amazing, especially being his first time. I could tell it was the orgasm of his life.

Brenda lifted her head to reveal her cum covered face and lips. He still had the occasional post cum shakes. “I’ll let that slide but don’t do that to your date..” she teased. He apologized and said he didn’t wanna make a mess of our couch and carpet. While she wiped his cum off her face and washed her hands, I told him some sex tips of my own so he would be able to last long enough and make sure he satisfied his date. He left shortly after.

A few days later, we heard back about his date. He said it went well and he even got to make out with her at the bar. He thanked us both for our help but said he might need more help depending on how their second date goes.