He chats with her just about every day because they are friends. They both work at their various jobs and they feel that it's always good to talk to someone that is not a co-worker during various points in the day on messenger. They have talked about everything from family to politics but more importantly, they generally talk about love and life. She has a boyfriend that she speaks very highly of and for the most part he is a great guy.
He, on the other hand, is single. He had a bad break up with a girlfriend about a year ago and heās still iffy about even having another relationship any time soon. Sure, he has plenty of female friends and a few jumpoffs here and there, but heās getting comfortable with just being alone.
Their friendship is a pretty good one. They have known each other for years after they met at a networking party a few years back at the Bronx Alehouse. They can talk about anything and have told each other their secrets. Actually, she has told him just about everything but he has kept one secret in his pocket. He has been dying to rub his dick on her lips.
He does find her very attractive and pretty much knows that they are not right for each other, but thereās something about her that just makes him hard. Perhaps heās curious about her or maybe itās the fact at her body is so on point. They did meet when he was with his ex-girlfriend and ironically she was single at the time. They got along very well to the point where his ex-was a tad jealous of her. There was always a hint of flirtation in their interactions and its something that has developed over time.
He knows that sheās not dumb. The flirtations are mutual but only go to a certain point. However, based on previous conversations, he wouldnāt be surprised if she already had a feeling about this. Of course, she has no idea as to what exactly he would like to do.
Heās imagined her naked several times. The few bikini pics that he has of her help his vivid imagination. She doesnāt believe in sending him naked pictures but has no problem letting him know that she has a Brazilian or that her nipples are pierced. He has stopped himself several times from saying the wrong thing. He would love to tell her that there are times that he daydreams of her being bottomless while sucking him off. He can imagine her head bobbing up and down until he comes. Heās never told her this because he respects their friendship, although there was a time he has come very close in telling her everything.
He gets to work today thinking that maybe he should just tell her and get it over with. They are friends and nothing will come from it because, after all, she will understand, right? Then he remembers something that was told to him by a much wiser man: A manās fantasy of women never meets the reality. He knows that heās hard up for her and any thoughts of anything happening is just all in his head--the one not attached to his neck.
He wonders what her response would be if he does finally tell her. As a matter of fact, if he was so bold, how would he tell her? Heās come up with a few ways to tell:
I wake up every day with a huge hard on and one of my first thoughts is to show you. He thinks that might be too much. She may not be into dick pics. Although, he does question if it is really that far fetched to assume she might actually wonder about his penis. Do women even do that? He thinks they do, which leads him to start thinking that maybe thereās a part of her that might think about it. There were so many times when he would wait for the perfect opportunity to tell her something completely inappropriate, which ultimately never came. Heād hope that one day she would say to him, ācan I ask you a question?ā His planned response, no matter what would be 9 inches. He would hope it would make her laugh but more importantly, we wanted her to know how big he is.
I really feel the need to tell you that I masturbated to your Instagram photo. Heās thinking that this may not help either. He was thinking about this one time when she posted a photo of herself that was so sexy that he imagined her deepthroating him. Still, this may not be the route to go.
I canāt help but fantasize about you. This may not be so bad, he thought. He knows there is a chance that he could offend her, which would suck. However, he maintains that they are good friends so maybe she will cut him some slack as long as he does not go too far. Telling her that he wants to lick that Brazillian may not win him any favors though. Although he wants to send her a gif that he found of this woman riding a manās face. With the way, her amazing ass looks he may want her to sit on his face for hours.
He has imagined her in every position possible, however, the one he normally settles on is doggie style. She has an ass that heās seen in yoga pants that are burned in his memory. He had wondered how much she would enjoy getting pounded. Coincidentally, when they did talk about sex, this one happens to be her favorite position.
He logs on to his computer at work after taking a few sips of his coffee. He takes a deep breath because heās going to go for it. He thinks about all the times he almost told her but backed off at the last minute. There was one time when she even told him that she canāt stop him from saying what he has to say, but still, he backs off.
His phone rings and as he begins to talk business, she messages him: My boyfriend and I broke up this weekend. We realized that this was just going nowhere. I would have called you this weekend but I just wanted to be alone with my thoughts.
Now, whatās he going to do? He might as well scrap all plans on telling her now, but he also canāt feel just a little excited of the possibility of her being single. This isnāt to say that her having a boyfriend would have prevented him from having sex with her if she wanted, but she is just not that type of woman. He does think that it is a shame that her relationship has ended. He has always commented to her that her boyfriend was a lucky man.
He does spend most of the morning consoling her. She is pretty upset but not distraught. His initial assessment is that this may not be a permanent break for them. He knows that she still loves her now ex-boyfriend and the door is open for his return. Still, he waits for a good opportunity to suggest they meet up for some drinks.
He goes into one of his daydreams where they go back to his place after drinks and she admits to him that she has been curious this whole time about him and had been staring at his crotch for most of the night. This, of course, leads to him fucking her mouth slow and steady on his couch. They are both naked and she devours every inch with such pleasure. She pulls up and smiles at him as he rubs the head of his cock on her lips. He knows that she loves to give head so it would only make sense to him that she would love to suck his. He snaps out of the dream when his boss walks asking a question about this morningās briefing. After the interruption, he realizes that he fantasizes about her way too much.
Itās not just about her giving him head either. He thinks about the entire dance. If there was ever a point where she told him that she just needed some oral attention, he would totally volunteer. He loves eating pussy and he would love having his head (the one on his shoulders) between her legs. The fact that she is waxed is a bonus.
What he really wants to do is fuck her hard and make her scream. He just never imagined so much lust can come from a friendship and he does want to tell her but now this break up has just happened which only means he will just have to wait.
A week goes by and she seems to be handling things pretty well. Their normal daytime chatting as moved more to phone texts in the evening and occasional conversations at night. He has been the friend that he should be. Supporting her in her time of crisis and making her laugh when she needs it. For the most part, he doesnāt flirt with her at all during this time. He knew it was only a matter of time until she would revert back to her normal fun loving self.
Today was a busy day at work, so he doesnāt log on to chat until the late morning. After finally getting settled in, she hits him up saying the complementary good morning. Ā She asks how he was doing and if he had a good weekend. Indeed he had a very good weekend and she knew that. He had a plan to get laid this past weekend and it worked out very well. He had shared with her that he was going to see an old flame for a possible hook up.
She wants to know the details of the encounter and as usual, he gives her a play by play of the night. He met up with his old flame and they caught up over some drinks which turned into dinner. The encounter was very reminiscent of times when they had fun. He eventually went over to her place and spent the night.
He describes everything about the date except for the end. Heās so very used to not telling her details about his sexual encounters. Of course, that is when she had a boyfriend, but heās still not used to her being single. They have boundaries and he was respecting them. They have talked about sex before in the ask-me-anything format. So they both knew certain things about each other, which is why his fantasies about her are so specific. She has mentioned to him that she loves to give head and that has piqued his curiosity.
But then the conversation turns to something he did not expect:
Her: So that is it. You just got laid? Was it good?
Him: Yeah, it was. Iām pretty sore in all the right places..or wrong places depending on how you look at it. lol
Her: Thatās awesome. I miss sex already. I still got a wax this weekend. I just like the feel of it.
Him: Wow. That sounds nice and smooth. I still donāt understand how you women do that.
Her: We are used to it. :)
Him: Can I say something that is inappropriate?
Her: Of course, you know you can say anything. Not like I have a boyfriend anymore.
Her: Is it about my wax? lol
Him: lol in a way it is. I feel that I should tell you that I have fantasized about you for a while and I never told you because you had a man. I know that we flirted a lot, well, at least I did anyway, but I respected you and your relationship. I donāt even know why I'm telling you this now.
Her: It's about time and we both know why you are telling me. lol
Her: Iām not surprised by any of this. I kinda knew. lol
Him: Did you? Was I that obvious?
Her: Of course you were. More importantly, I know you.
Him. Well, I thought you might have known, but I was never sure.
Her: You know you can tell me anything. We are so passed the awkward stages of our friendship.
Her: So are you going to share what you think about?
He sits back to think about this. He was totally caught off guard with her response. He doesnāt even know where to begin with her. His heart is racing and he is throbbing with excitement because of the realization that she knew all along.
The first thing that comes to mind was a picture she sends to him months ago. There was nothing openly bad about this picture. It was a normal selfie that anyone would see anywhere. She is posing in front of a mirror showing off her new hairstyle. Itās a full body picture in which she is fully clothed with jeans on and a top that exposes her belly a little bit. Not a big deal, until she mentioned to him that she sent the same picture to her man but in that picture she was bottomless. He was almost beside himself when she told him that. He had such thoughts about what that picture must look like and if he ever got a copy of that he might explode. He was always dying to see that picture, but nevertheless, it was deemed boyfriend worthy.
Him: Do you remember that picture you told me about that you sent to him and you were bottomless?
Her: Yes. lol the boyfriend only picture.
Him: I have been thinking about that for some time. I have been imagining you freshly waxed.
Her: Wow! That was months ago and yes I was indeed very smooth when I took that pic. Iām still really surprised you never told me sooner. I had a feeling you wanted to see that picture too. lol
Him: Again, I was nervous about how you would take it.
Her: I understand. Was that the only thing you thought about?
Her: Tell me more. Iām curious.
Him: Well there was this Instagram photo you posted a while back. It was a selfie from when you first started your new job. It was an amazing pic that I just loved.
Her: That is nice. But I feel there is something you are not telling me, you can be honest.
He knows he has to make a decision here. Once he tells her this, there is no going back. There was a time when he woke up with a hard-on and before he decided to take care of it, he pulled up this very same picture on his phone and stroked himself to it.
Him: To be honest, I imagined you giving me head.
Her: Interesting. Something tells me you imagine that a lot. lol
Him: You have no idea. lol
Him: Can I be blunt with you?
Him: Yes, I think about you sucking my dick a lot. I remember a time when you said that you love to swallow and right there I was envious of your ex-boyfriend. I just had this feeling that you would suck him off anytime he wanted.
Her: and I did. You arenāt lying, I do love giving head.
Him: I hope I didnāt weird you out with any of this. You have been a good friend and I wouldnāt want to ruin that.
Her: We are fine. You truly a dear friend and if this was weird in any way I would not have entertained this conversation.
Him: So then what are your feelings about this?
Her: You know I have always thought you were handsome and when I think about it, I sent you some pictures because I wanted you to look. I knew they turned you on and it made me feel good about myself. Overall, I have has some thoughts of what it would be like. I mean, there are times when you have made innuendos about your penis so naturally, Iāve wondered what it looks like and how big it is. lol
Him: You know I could have sent you some pics.
Her: lol! yes, I know but I donāt like cock pics, they are crass and men too many men send to women unsolicited like we want to see them. Besides, when I want to see a manās dick it should be in person. But, listen, I need to head to aĀ meeting. I just send you a text. I should back later in the day. Enjoy!
He checks his phone and beholds the picture he been craving to see. He stares at her bottomless beauty. She is also angled in such a way that he can see the curvature of her amazing ass. His cock throbs in his pants. Maybe he will live this fantasy after all.
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