Best friend offers Her boyfriend to take Katie’s virginity.
By DanDraper. Listen to the Podcast at Steamy Stories.
KATIE’S STORY
Katie woke up feeling like shit. She laid in bed wondering what the hell she was thinking of drinking as hard as she did last night. It took her a few minutes to realize she was fully naked under her blanket and suddenly remembered the incredibly handsome man she was hanging out with at the bar. She looked over at the other side of her bed. He was not there, nor were there any signs that he was around.
She remembered him taking her home and her having to drag him into the bedroom. She thought long and hard, trying to remember if they had sex or not.
“Oh, I remember now,” she said to herself.
It took a moment, but she suddenly remembered feeling very sick. The guy recognized that she was going to throw up and quickly took her to the bathroom, got her head in the toilet, and she vomited like she had the Spanish flu.
After that, everything was very hazy. She had no idea how she got naked and into her bedroom, or if she had had sex with the man she met. She doesn’t feel like she had sex, but then again, she wouldn’t know how it would feel afterwards. Katie was a virgin, or at least she thinks she still is, depending on what happened to her last night. She was setting out to finally have sex but was hoping to remember the experience as she hadn’t planned on drinking so heavily.
She heard a noise outside of her bedroom, she could tell there was someone in her kitchen. If it was the man she took home last night, he could shed some light on the subject. She found some clothes to quickly put on and left the bedroom. She was incredibly nervous about seeing that man. She hoped she hadn’t fully embarrassed herself in front of him.
As she reached the kitchen, her nervousness went away and was replaced with disappointment. It was not the sexy man she hoped she had sex with, but her best friend Jennifer, making coffee.
“Good morning, sunshine,” said Jennifer.
“Good morning,” Katie replied. “This is going to sound awkward, but did you see someone else around her before?”
“Oh, you mean that super sexy Marine you took home last night?” Jennifer asked. “I have to say, you’ve got good taste.”
Katie sat at the kitchen table, trying to ignore the massive hangover headache she was getting.
“I don’t remember much after I vomited last night. I’m trying to piece together what happened.”
“Let me fill in the gaps for you,” said Jennifer, as she got two cups of coffee ready for the both of them. She handed one to Katie and took the seat next to her. “He took you home because he saw how drunk you were from the way you were all over him despite how much he resisted your advances.”
“He resisted me?” Katie asked. “I thought it was mutual.”
“You were drunk, you thought what you wanted to think,” Jennifer reminded her. “So, after he took you home and you repeatedly tried to get him to fuck you, but he didn’t, he saw you were going to throw up and took you to the bathroom. After you vomited and began crying on the floor.”
“I cried, oh no,” Katie said, looking very embarrassed.
“He then looked through your phone and called me. When I came, he helped me get you washed up and undressed and took you to bed before he left, and I slept next to you all night.”
“Oh God, I feel so stupid,” said Katie as she took a sip of her coffee. “Did the marine leave his number by any chance?”
“Katie, that guy was gay,” Jennifer revealed. “I know because when I arrived, I first accused him of trying to take advantage of you. That’s when he told me he was gay and showed me proof by showing me photos on his phone of him and his boyfriend, some of which had them making out with each other.”
Katie felt like the biggest idiot in the world. She couldn’t believe she spent the whole night hitting on a gay guy.
“That means, it was all for nothing,” Katie began to say. “That means I’m still a ..”
Katie stopped herself before she revealed anything she didn’t want Jennifer to know.
“Yes, you’re still a virgin,” said Jennifer. “The gay marine told me that’s what you were crying about after you vomited.”
“Oh, shit.”
Katie felt incredibly embarrassed. It was a secret she was trying to keep from everyone.
“I can’t believe you never told me you’re still a virgin,” Jennifer snapped at her. “I’m your best friend; these are things you should be telling me.”
“It was embarrassing to be a woman my age and still a virgin. I couldn’t tell you or anybody, let alone you.”
Katie and Jennifer both grew up with religious families and went to the same strict Catholic school where they met and became best friends. Katie was always the more religious of the two, while Jennifer was the more fun one who was more obsessed with boys. Jennifer was the first of their entire group of friends to have sex in their senior year, while the others lost their virginities throughout their senior year.
Katie lied to her friends in order to impress them by saying she had sex with her then-boyfriend after their senior prom at a hotel they got. She had planned to lose her virginity to him, but right before she was going to get undressed for him, her Catholic guilt got the better of her and she began crying, telling him how she couldn’t do it. Her boyfriend did not want to put any pressure on her and told her she didn’t have to do anything she didn’t want.
After that, she told him he could tell his friends they slept together because she knew he was also looking forward to it. She felt embarrassed about still being a virgin herself, so she lied to her friends about sleeping with him and how great it was.
Over the years, she made up excuses not to sleep with the men she dated, often because of her religious beliefs. To avoid embarrassment, she lied about the men she had slept with to her friends; never too much to make herself look like a slut, but not too little to make herself look like a prude either. When pressed for details, she kept it vague and said what she thought was right.
She had hoped that she would eventually find the right man, get married, and it would all be over. But she was on the verge of turning 30, and it was getting too frustrating for her. At that point in her life, she didn’t care what her religious beliefs told her about waiting for marriage; she just wanted to get laid.
In the last year, Katie had tried to have sex with the few men she dated, but she was having incredibly bad luck with them; one guy turned out to be married, another also had religious hang-ups about sex, and two others were just straight-up jerks to her. She was close to two other guys, one who had a bad case of premature ejaculation and always shot his cum right before they got to business, and another who couldn’t get it up at all and refused to get Viagra.
She tried to do an online hookup using Tinder and other similar apps, but found that some of them were straight up creepy. She didn’t know how some of her other friends were able to find online hookups without getting stalked by some of those weirdos. One guy she found online seemed like an ordinary guy until she found out he wanted them both to have sex while dressed in fluffy animal costumes; she couldn’t get away from him fast enough.
After getting a little desperate because she was less than a week away from turning 30, she decided to just meet a guy at a bar for a random hookup. She went to a bar that was frequented by military types, hoping to be fucked by a handsome war vet who had just come back from overseas. She heard from her friends how good in bed most of them were and hoped it was true. She only drank to calm her nerves about being there for a hookup, only to find herself drinking too much and not realizing she was hitting on a gay guy the whole time.
Katie confessed everything to Jennifer, who still looked dumbfounded from hearing how her best friend was still a virgin.
“This is unbelievable,” said Jennifer. “Those nuns at Catholic school really did a number on you.”
“I’m surprised I didn’t become one of them,” Katie replied.
Jennifer was surprised that Katie had no luck getting a man to sleep with her. She would’ve figured she could’ve had any man she wanted. Katie was a very attractive woman, with long red hair and a decent figure. Her breasts weren’t huge, but she had seen her naked and could tell she had a good pair on her that most men would love to get their hands on.
“So, you had no sexual experience whatsoever?” Jennifer asked. “Like, other things besides intercourse?”
“What do you mean by that?” Katie asked.
Jennifer motioned with her hand to mimic giving a handjob.
“Oh, yeah, I have given plenty of handjobs,” Katie revealed. “I had to eventually do something to keep some of the men I dated happy. And in the last few years, I learned to give oral sex as well, and let guys finger me.”
“At least you’ve done something. So, I understand why you went to that bar last night, so let me help you with your problem.”
“Help me how?” Katie asked.
“I’m going to help you get laid, of course,” Jennifer replied. “You have three days before you turn 30, and I’m going to hook you up.”
“How are you supposed to do that?”
Jennifer assured her, “Just leave it to me. You were ready to find yourself a random hookup. I can find you that hookup myself.”
“So, you’re just going to get me a guy to help me get laid as if it’s that easy?”
“Do you want to be a virgin in your 30’s?” Jennifer asked.
“No, of course not.”
“Then just leave it to me.”
JENNIFER AND JOSH
Later that day, Jennifer’s boyfriend, Josh, came over to her apartment for dinner and a movie, and, of course, to spend the night with her. The dinner was alright. Jennifer had become a better cook than she was when they first met, especially since he gave her advice on how to improve her cooking skills.
After dinner, Jennifer brought out a cake for dessert. She bought it from a bakery as she had failed in her last few attempts at making one on her own.
“How’s Katie doing after last night?” he asked.
Josh was there when Jennifer got the call. They were about to go to sleep after fooling around when her phone kept going off, and she answered it, thinking it was Katie, when it was some other guy who took her home. As Jennifer explained to him what had happened to Katie, he tried his best not to laugh at her situation, especially the part where she found out the marine that she was hitting on turned out to be gay.
Afterwards, Jennifer told Josh about Katie’s big secret and was floored when he heard it. He knew she was very religious, but never thought she might be a virgin. He knew a lot of religious people growing up, and they never stayed virgins for that long. Even the few religious girls he dated before Jennifer liked to fool around.
“I can now understand why she wanted a bar hookup,” said Josh.
“So, that brings me to what I need to ask you. I want to help her get laid before she turns 30 in a few days, and I thought maybe you know someone among your group of guys who could help her out.”
“You want to set her up with one of my friends for a random hookup?” asked Josh. “How about I hook her up with someone to date? I know a few who are good boyfriend material for her.”
“No, she needs to get laid fast. Dating could take time before sex. I know some people move fast these days when dating, but not always.”
“Ok, I guess I can think of one or two people who could help,” Josh told her.
Josh thought long and hard, thinking about every one of his friends and even considering his brothers and a couple of cousins. For everyone he thought of, he could find a reason why they wouldn’t be a good idea, even for just a hookup. A lot more of his friends are either married or in some other kind of relationship these days. A few others now live too far away and probably won’t travel a few hours just for a hookup, no matter how horny they may be, especially at such short notice. There were one or two guys he knew of who were definitely into random hookups, but they were such jerks, he couldn’t do that to Katie. There were a few others, but they were more of the relationship type of guys, not the random hookup types.
“So, can you think of anybody?” She asked because Josh was taking a long time coming up with a name.
He told her, “No, I can’t think of anybody. Everyone I know has a reason why I can’t suggest them.”
Jennifer felt very disappointed. She was really hoping Josh could come through for her. But after he explained to her all the reasons, he couldn’t suggest any one of them. She had no choice but to agree with them. He apologized for not being able to help, but Jennifer said he didn’t have to because it wasn’t his fault. She told him to forget the subject and they cleaned up the table to be ready for the movie they were going to watch.
They were on an 80’s movie binge over the last month, watching some of the best films of the decade. They didn’t go in any particular order, just randomly choosing whatever film from that era they wanted to watch. Tonight’s film was “The Big Chill” from 1983, about a group of former college friends who spend the weekend together after the funeral of one of their friends. They loved the movie; it was a funny yet heavy-hearted film.
One of the things Jennifer found most interesting about the film was how the character Sarah wanted to help her friend Meg, who wanted to have a baby by getting her husband Harold to sleep with her. It was an incredibly awkward situation for someone to ask their husband to knock up one of their closest friends, but she convinced him to do it and they still remained friends afterwards.
Jennifer was surprised that the character of Sarah came to that kind of decision, but definitely understood; when your friend is in need of something, you would do anything to help them out. She found this relatable to her own situation with her best friend Katie and came to the decision that she should offer up her boyfriend just for one night to help her lose her virginity.
She wasn’t going to ask Josh about this right away after the movie ended, so she decided to wait until the morning to bring it up. When the film was finished, they discussed the film for a while, telling each other what they liked most about it. Afterwards, they went to bed to make love, and he spent the night.
In the morning, Jennifer woke up earlier than Josh to make his favorite breakfast, blueberry pancakes. She knew she wasn’t that good of a cook, but she was a queen at making pancakes. She had gotten a good stack ready for him just as he came into the kitchen.
“Oh, nice,” he said as soon as he saw the pancakes. “What’s the occasion?”
“Just because I like you so much,” she told him.
They gave each other a big kiss and sat down to eat breakfast. Jennifer wanted Josh to be extra happy to make him ready to ask him her big favor.
“What do you think about Katie?” she asked.
He replied, “She’s a great person.”
“Do you think she’s pretty?” she asked.
Josh had to think about that for a moment because it sounded like a trick question; most women don’t ask if their boyfriends think their friends are pretty.
“And before you have to think about it, this is not a trick question. I generally want to know,” she assured him, because she could see he was worried about answering the question honestly.
“Ok, yeah, she’s a pretty girl,” he responded. “It makes me more surprised she’s still a virgin; I would’ve figured a lot more guys would be all over her.”
“Yeah, it’s too bad she couldn’t find the right one to show her how wonderful sex could be.”
“If you want, I could still set her up with the guys I said would be good boyfriend material,” he told her. “She may still have to be a virgin after she turns 30, but she could wait a little longer.”
“I think I know one guy in particular who could help her with her situation,” said Jennifer. “A wonderful man who I know personally is amazing in bed.”
She said that last part as she grabbed his hand and looked deeply into his eyes.
“Where are you going with this?” he asked. He had his suspicions but wanted to hear it from her.
“I think you should be the one to take Katie’s virginity,” she finally revealed.
Josh burst out laughing, assuming Jennifer was making a crazy joke. After he finished laughing, he saw in her face how serious she was.
“Oh shit, you’re serious?” he asked.
“Yes, I’m serious. She knows you, she’s comfortable around you, and I personally know you can show her a good time in bed.”
“What made you think this would be a great idea?”
Jennifer reminded Josh about the move they saw last night and explained the reasons why it would work.
“That was just a movie,” he told her. “No woman in real life would offer up her husband like that, let alone her boyfriend.”
This was not going as smoothly as she hoped it would. She thought Sarah convinced Harold and Meg too easily to sleep with each other, and it did look like the movie never fully showed the conversations she had with them to convince them either. She still had to try nonetheless.
Jennifer continued to say, “I still think it should be you. If not, she may not have that chance for a good long time. Even if you do set her up with one of your friends, who knows what could happen in the long run? She needs this before she turns 30.”
“Is having to do this before she’s 30 really that important?”
“Would you have been OK with being a virgin after 30?” she asked in response.
Josh thought about it for a moment. He lost his virginity just after he turned 18, almost 15 years ago. He was no Casanova, but he did alright over the years with women until he met Jennifer, the best relationship he ever had. He would do anything for her, but he never expected her to ever ask him something like that.
He thought about Katie’s situation as well. Being a virgin at 30 was kind of bad, although not unheard of in these modern times. He thought it was a bad idea, but at the same time, he couldn’t help thinking how Katie nearly got into a bad situation the night before.
“I can’t help thinking how lucky she was to have run into a gay guy who helped her out the other night instead of some creepy dude who would have taken advantage of her and possibly hurt her. She is very naïve when it comes to this stuff, isn’t she?”
“Yes, she is,” Jennifer replied.
“And you’re sure you would be OK with this?” he asked.
“It’s just one night, you would be helping someone out greatly, and our love is strong enough to overcome any kind of awkwardness about it.”
He thought about it some more, needing to be absolutely sure it was definitely a good idea. It may be an easy decision for some men. Some of his friends would’ve said yes right away, not caring about any consequences. But he was a different kind of man. He felt there were lines you shouldn’t cross, and he never cheated on anyone. Technically, he would not be cheating since it was done with Jennifer’s encouragement, but it was still very similar.
“So, is that a yes or not?” she asked demandingly.
“Hey, give me a break. You just sprung this on me like five minutes ago, and it’s still early in the morning.”
She backed off to let him think about it some more, but she was getting anxious for an answer. She watched him eating his pancakes as he continued to figure out all the pros and cons of the situation. She couldn’t blame him. As much as she hoped for a quick yes answer, she knew it was a highly unusual request.
“Ok, I’ll do it,” he finally answered. “Only because I don’t want her in another situation like she was in the other night and at least I can prepare her for what she may experience.”
Jennifer was so excited that she grabbed Josh by the shirt collar and pulled him in for a big, passionate kiss. She let him go, and he had a big smile on his face.
“You’re the best boyfriend,” she told him.
“Just so we can clear the air here, you’re happy that your boyfriend is going to be sleeping with your best friend?”
“Yes, I am aware of that.”
“Whereas most women never want that to happen for very obvious reasons?”
“Yes, I am aware of how weird all of this is, but I assure you that I am very much OK with it,” she assured him.
They continued eating their breakfast and discussing the situation some. The only thing she now had to do was convince her best friend to sleep with her boyfriend.
JENNIFER AND KATIE
“Are you out of your mind?” Katie asked.
“Listen, I know this all sounds a little crazy..”
“Not a little crazy, a lot crazy,” said Katie.
It was later in the day, after Jennifer had her big conversation with Josh. She was sitting with Katie at a booth in their favorite restaurant, where they often met for dinner. Jennifer invited her to dinner to discuss a guy she wanted to hook her up with to help her lose her virginity, and Katie was very excited about it. When she said it was someone that Josh knew, Katie was hoping it was one of his cute friends, but she did not expect it to be her Jennifer’s boyfriend.
“I’ve thought this through; it’s a perfect idea,” said Jennifer. “And Josh is all for it.”
Katie looked very surprised. She didn’t think she had talked to Josh about it already and that he was somehow OK with the situation.
“Seriously? He wants to sleep with me?”
“It took some convincing, because he didn’t say yes right away, obviously. But in the end, he thought it was a great idea.”
“You’re asking me to sleep with your boyfriend,” Katie replied. “What made you think this was a good idea and that I would say yes to it.”
“Have you ever seen the movie The Big Chill’?” Jennifer asked.
“Are you serious? Harold and Meg? That’s what made you think this would work?”
Jennifer was surprised that Katie had already seen the movie, but it did make it easier for her to discuss it with Katie.
“It worked out in the movie. Sarah cared about her friend so much she offered up her husband to get her pregnant, and afterwards, Sarah and Meg were still friends, and it didn’t ruin her relationship with Harold.”
“That was just a movie,” Katie replied. “But you don’t actually see how Sarah convinced Harold and Meg to sleep together, because the writers knew there was no way to make a conversation realistic enough to show how it would be so easily done.”
“Oh, wow, I never thought of it like that.”
Katie continued, “Also, they had artificial insemination back then. Why didn’t Sarah just ask Harold to just be a sperm donor and go to a clinic to get it done?”
“Meg was ovulating during that weekend. It had to be then.”
“They still could’ve waited another month,” Katie replied. “Also, there was no telling if she would get pregnant the first time. If she didn’t, does that mean she’d have to keep coming back to sleep with Harld until she does?”
Jennifer had to think about that whole scenario in that movie. She could now see that there were some plot holes there.
Jennifer continued her argument. “Ok, you’re right about the movie. But I’m still right about this. Josh would be a great person for you to finally experience sex with, and you should do this before you actually turn 30. Being a 30-year-old virgin is not unheard of, but it’s not something anybody wants, and I know you don’t want that, which is why you’ve been trying extra hard this past year to get laid.”
“I can’t believe it’s actually that hard for me to get laid,” said Katie very sorrowfully. “I’m an attractive woman. I should be having more men coming after me and getting me into bed with them.”
“You can question your bad luck with men as much as you want, but you don’t have much time to get this kind of opportunity.”
Katie thought about it long and hard. It was a good offer, and she had always thought Josh was a very sexy man and was often jealous that Jennifer got to have a guy like him. But it was still a very unusual situation; women don’t usually ask their best friends to sleep with their boyfriends, after all.
“Listen, I have to admit, I do like that idea,” Katie finally admitted. “If my situation was different, it would definitely be a hard no.”
“But you do like that idea,” Jennifer said with a grin.
“Yes, but I feel like a bad friend for even considering it, despite how much you’re OK with it. This is not what best friends do to each other, no matter what the situation may be.”
“Listen, I understand,” said Jennifer as she reached out and held Katie’s hand. “But I don’t think you would be a bad friend for saying yes. I love this idea, and I think it would be a wonderful thing.”
Katie had to think about it long and hard, making Jennifer anxious to hear her decision. She wanted to say some more things to Katie to convince her to say yes, but she didn’t want to push her.
“Ok, I’ll do it,” Katie finally answered. “If you and Josh are OK with it, I’ll do it.”
Jennifer almost squealed in excitement. She never thought she would be happy to get her best friend to sleep with her boyfriend.
“Ok, I’ll let him know you’re all aboard and make sure he comes by tomorrow night, so you better be ready for him.”
“What? Tomorrow night?” said Katie very nervously. “Oh my God, I just remembered that tomorrow night is the last night of my twenties. I don’t know if I can be ready in one day.”
Katie was breathing heavily, thinking about the situation and how soon she would finally be having sex.
“Don’t worry, you’ll be fine,” Jennifer assured her.
“What if I’m terrible?” Katie asked. “What if Josh doesn’t do a good job?
Jennifer put her hand over her mouth to muffle the laugh she was about to make. It took a few seconds for her to get control of herself.
Jennifer assured her, “Trust me, sweetie, he won’t disappoint you. If he wasn’t that good in bed, I wouldn’t be with him right now, no matter how well we get along in everything else.”
KATIE AND JOSH
Katie spent the majority of the day both getting ready for her big night and panicking about it. As much as she was assured by Jennifer that everything would be alright and she would have a great time, she was still incredibly nervous. Even her old Catholic guilt was starting to come back, telling her she was going to hell for this. But she realized it was all just nerves and that it would go away.
At exactly 7 p.m., there was a knock on the door, right when Jennifer said Josh would arrive. She was impressed with how punctual he was, but she didn’t know that Josh had actually come 15 minutes earlier and was just hanging around the hallway outside Katie’s apartment, getting himself ready for what he was expected to do. As confident as he usually was, he was incredibly nervous; even with Jennifer’s encouragement, it was still an unusual situation. He took those 15 minutes to get himself prepared to meet Katie, telling himself that he was not just helping his girlfriend’s best friend, but someone he thought was a friend also.
Katie answered the door and saw Josh standing there in a suit with no tie. She thought he looked incredibly handsome standing there; he was tall, clean-shaven, and muscular with short black hair.
Josh also thought Katie looked beautiful in her short black dress that showed a small amount of cleavage on top. He still couldn’t believe that this beautiful woman standing before him was still a virgin.
They greeted each other, and she asked him to come in. Josh handed her a bouquet of flowers.
“Oh my God, you didn’t have to do this,” she said gleefully. “Was this Jennifer’s idea?”
“No, it’s all me,” he told her. “I just thought it somehow seemed appropriate.”
Although the flowers were his idea, he didn’t mention that Jennifer helped him pick out his clothes for the occasion.
“They’re beautiful. Thank you.”
She led him to the kitchen to put the flowers in a pitcher she had and filled it with water; the pitcher would work until she found a vase for the flowers.
At the kitchen table, Josh saw that Katie had made them both a fancy dinner. He was impressed with how the food looked and smelled.
“You didn’t have to make us dinner.”
“I felt like I had to,” she replied. “I didn’t feel right with you just coming here and us going straight to the bedroom. It made me feel kind of…”
“Nervous,” he said, trying to finish her sentence.
“Slutty,” she replied. “I know it sounds strange, but I feel slutty just taking you straight to the bedroom.”
“I see,” said Josh. “If it makes you feel better, I don’t think you’re slutty at all.”
“Thank you, it does make me feel better,” she replied. “Also, I thought we could have a nice dinner and have some fun eating and talking before we… you know… get down to business, I guess you can say.”
Before they took their seats, Josh took off his suit jacket and put it on the back of his chair while Katie tried to open a bottle of wine for them. Josh saw she had trouble with the bottle and insisted on opening it himself and pouring it into both of their wine glasses.
He was impressed with the meal she had made. Katie told him it was parmesan risotto with roasted shrimp. He felt like he was in heaven after his first bite; he was surprised that someone who was so close to Jennifer was a better cook than she was. He told Katie how wonderful it was, and she was glad to hear it.
They talked a little while they ate, talking about a variety of things. They were surprised at how much they had in common. They did their best not to talk about Jennifer; they didn’t say it to each other, but they both figured talking about her would kill the mood for what they were going to do later.
“This meal was fantastic,” said Josh as he finished his last bite. “I’m surprised you’re not a chef.”
“If you think that’s good, wait until you taste the dessert I made.”
“Wow, after seeing how good this meal was, I would love to eat whatever you made for dessert,” said Josh.
There was a long pause, and Josh noticed that Katie had something to say.
“Is something wrong?” he asked.
“Nothing is wrong,” she assured him. “I just think we should skip dessert and go straight to the bedroom.”
“Are you sure you want to do this now?” he asked.
“Yes, now is the perfect time,” she replied. “We are having a great time together; I feel very comfortable with you and I don’t want to waste any time.”
She said this with a big smile on her face, and Josh could tell she was very happy and excited. He was glad she felt that way.
“Ok then, let’s do this,” he said, with a big smile of his own.
They took one last sip of their wine and left the kitchen.
She led him to her bedroom; he could tell she didn’t know what to do next, so he took her by the arm and gently took her to the bed where they sat on the edge. He didn’t waste any time as he leaned in and kissed Katie on the lips. They held that kiss there for a moment before Katie pulled away from him.
“I am on the pill, by the way,” she assured him. “We forgot to talk about birth control, so I should let you know so you don’t have to worry about anything.
"Thanks for letting me know. I had a condom ready, but this is better.”
They went back to kissing. It started as a passionate kiss that evolved into a full-on make-out session as their hands began roaming each other’s bodies.
Without thinking about it, Katie began unbuttoning his shirt and taking it off for him. She broke their kiss so she could look at his chest and broad shoulders.
“Oh my,” she said with a big smile.
They began kissing again, and this time she went for his pants; ripping off his belt and going for the zipper. In return, Josh reached around her back and undid the zipper; he pulled down her dress to reveal the sexy black bra she was wearing and soon her matching thong. Katie thought hard about the kind of underwear she should wear and figured she couldn’t go wrong with traditional black lingerie.
They both got very excited and quickly took off the remainder of the clothes and tossed everything around the room. Katie was both shocked and happy to see the size of Josh’s dick. Jennifer had bragged to her about how big it was, but she thought she was exaggerating; she was glad to see that it was all true.
Josh got Katie on her back in the center of her bed. He started kissing her neck and fondling her breasts; she loved it and was getting very wet. Josh then moved down to her breasts, where he spent some time kissing and suckling on her nipples. He thought her breasts felt like two soft pillows and loved how they felt on his face.
He moved back up her body and began kissing her neck again. As he did that, he put his hand between her legs and began to play with her clit. She started to get wet instantly and began taking deep, rapid breaths.
“Oh yes, keep doing that!” she cried out.
He knew she was ready and didn’t want to keep her waiting. He positioned his body right on top of her and guided his dick right to the edge of her pussy and shoved it all in. Josh held it there for a moment to enjoy the feeling of being inside of her. He could see from the look on Katie’s face that she also enjoyed that incredible feeling.
“Oh my God, that feels wonderful,” she whispered into his ear.
He started pumping his dick into her. Slowly at first, to get her used to it, then gradually picked up the speed and pushed into her harder and faster.
“Oh yes, oh yes,” she cried out.
Katie held him close to her body, letting out loud moans every time Josh pushed himself into her body. She begged him to go faster, and he complied as best he could. Her body arched up as she screamed as an orgasm shot through her body.
They turned over, and she was on top of him now. Katie had her hands firmly placed on the headboard when she began riding his dick. She didn’t really know if she was doing a good job of riding him, but she still loved giving it a try and was having so much fun doing it. Josh had his hands on her hips; he was getting very excited about watching this beautiful woman enjoy herself as she rode him.
Josh got her on her back again and pinned her hands by her side as he began fucking her hard again. She was screaming into his ears, begging for more. After a while, he couldn’t hold off much longer and got that feeling in his dick that it would soon be over. He held off for a couple more minutes, wanting to make it last as long as he could. Then, with one last thrust, he shot his load right into her, and she enjoyed feeling that warm liquid filling her body.
Afterwards, he lied down next to her as they both took their time relaxing.
“Thank you, that was amazing,” she told him.
“I’m glad you liked it,” he replied. “I’m glad I got to be the one to do this for you.”
“I have one last request,” she said as she looked deeply into his eyes. “Can you stay the night with me? I just like the idea of the man I finally got to have sex with spending the night with me.”
“Of course, I was thinking the same thing. I didn’t think it was right for me to just have sex with you and leave right away.”
She pulled a blanket over their naked bodies as Josh turned off the lamp next to their bed and they snuggled up against each other. A moment later, she felt something moving along her leg, and it took a moment for her to realize Josh was getting an erection again.
“Seriously? It can come back that fast?” Katie asked.
“Depends on the guy, but yes, it can happen again that fast,” he replied.
Katie reached down into his body and felt Josh’s dick, giving it a soft rub up and down. She was doing her best to impress Josh with her handjob skills, and she could see from his face that he was loving it.
“You know, Jennifer didn’t actually tell me we only had to do it once,” she said. “She only suggested it would be just one night together.”
Josh thought about it for a moment, at least the best he could with the handjob he was receiving.
“That’s what she said to me too,” he told her. “Seems kind of vague to me. For all we know, she meant for us to do it more than once.”
They moved in closer to each other and made love one more time that night before they actually decided to go to sleep.
The next morning, they woke up at the same time, while holding each other.
“Good morning,” said Katie.
“Good morning,” Josh replied. “And happy birthday.”
“Oh right, I’m now 30,” she said with a large smile. “After last night, I feel like I’m 20.”
They kissed each other, and Katie felt his dick growing up against her leg again. She reached down and began jerking him off.
“Seriously? Again?” Josh asked.
Katie didn’t say anything, she just tossed the covers away and moved down his body. After giving him a good handjob, she opened her mouth and started sucking his dick. Jennifer did tell him that Katie had told her that she had some experience keeping some men happy while she stayed a virgin. That included giving oral sex, and he could see how great she was at it.
When she was done, she took his dick out of her mouth and got on his body. She got his dick in her again and started riding him like she did last night, but much better this time. She knew deep down she shouldn’t be fucking her best friend’s boyfriend more than that one time, but she couldn’t help herself.
Josh turned her around to be on top of her and took over, fucking her. He did everything he did with her both times last night and brought her to orgasm a few more times.
After they were done, they again laid down on the bed, holding each other. They both agreed that it should stop right there, as three times was more than enough.
They got out of bed and got dressed. Katie put on jeans and a t-shirt, while Josh, who hadn’t planned on staying overnight originally, only had his suit pants and shirt to put on.
They heard a noise in the kitchen and wondered what was going on out there. Then they smelled coffee and pancakes and had a guess on who it might’ve been. They left the bedroom and went to the kitchen, where they found Jennifer in Katie’s kitchen, having just gotten coffee and pancakes ready for the three of them.
“Good morning, lovebirds,” said Jennifer.
“Good morning, Jennifer,” said Josh.
“Good morning,” said Katie.
Jennier went over to Katie and gave her a big hug and a kiss on the cheek.
“And happy birthday to you, sweetie. Did you have fun?” Jennifer asked.
Katie blushed and smiled at Jennifer. “Yes, I did very much. Best birthday present ever.”
They all went to the kitchen table to sit down for the breakfast Jennifer had made for them.
“I know this looks strange with me coming here like this, but I was afraid after last night that things may feel a little weird between the three of us,” she told them. “So, I thought I’d come over and make us some breakfast to help us overcome any leftover awkwardness between us.”
Josh agreed. “That’s a good idea. I mean, I know we can get over the unusual aspects of this situation, but it’s still good to get it out into the open.”
“Yes, I’m sure we can get past anything,” said Katie. “And also, thank you both so much for last night.”
“It was our pleasure,” said Jennifer as she held Josh’s hand. “And speaking of that, I really need to say something to get it out of my system. I did hear you guys have sex again this morning.”
Josh and Katie gave each other a concerned look.
Jennifer continued, “Thinking about it, I didn’t say how many times you two could have sex, but I did expect it to be only once. I just need to know how many times exactly you two had sex.”
There was an awkward moment at the table before Katie spoke up.
“We had sex three times,” Katie revealed. “I’m sorry, I couldn’t help myself.”
“It’s OK, I’m willing to let it all go. I was the one who encouraged you two to get together after all, so I can’t blame you for going that extra mile,” said Jennifer. “I’m just glad you both had fun.”
“Thank you, you’re a wonderful friend, Jennifer,” said Katie, then turned to Josh. “And you’re a wonderful man.”
“Thank you,” Josh replied, with a blushed face.
“Now tell me, was he as good as I told you he was?” Jennifer asked.
The two women began laughing, and Josh just sat there looking embarrassed.
“Yes, he was,” said Katie, with a big smile. “You would be proud of him.”
They ate their breakfast and changed the subject to a variety of other subjects to talk about. Afterwards, Josh and Jennifer left the apartment. Although it was early in the morning, Jennifer took Josh back to her place to reward him for a job well done.
Later that night, Jennfer took Katie out for her thirtieth birthday with some of their closest friends. They first went to a restaurant to celebrate with a big dinner and a birthday cake. Later, they went to a male strip club to party, where Katie got drunk and found herself making out with one of the male strippers. She wanted to take him back to her place, but Jennifer recognized how drunk she was to make any rational decisions, so she dragged her away and took her back home.
Over the next year, Josh set up Katie with the two friends he had tried to suggest before that could be good boyfriend material for her. Each relationship lasted only a few months before they broke up; they all agreed there was nothing wrong with the other person; it just didn’t work out. From what he heard, she did sleep with both of them, and later, Jennifer revealed to him that Katie became friends-with-benefits with the second one.
The next year, Katie began dating a man who had just moved into her apartment building and turned out to be the love of her life. They became engaged within a year, and they had a quick wedding as Katie found herself happily pregnant with twins.
By DanDraper for Literotica