Sugar Daddy

I Don't Feel Comfortable

For the next couple of weeks, things were pretty chill. I had gone out with Oliver 4 more times, but still no sex. It feels like he's afraid to ask, even though we have been very close during our last 2 dates. Me on the other hand, I am too shy to ask or to show initiative and lead things there. All the sexual tension makes me go crazy, resulting in me giving my all to the things I send to Aaron.

The one thing I can't send him though is a video of me masturbating. When I even think about recording it while I'm doing it, I flip. The month is ending soon and I should at least send him one of this kind of video. Maybe if I could ask him to be a little patient and explain to him how I feel, he will understand. Worst case scenario, I get less money...

So, that's what I did: One Sunday morning, I send him an email, saying that I want to talk to him about something important, so he immediately asks me when I'm available. Thankfully I'm free the exact moment he replies, so he video calls me on Instagram

"Good morning..."I say shyly, while still trying to figure out what to say to him

"Good morning! Everything ok? U scared me a little..."

"No no! Everything is ok...I just wanted us to discuss something..."

"Ok, I'm all ears..."

"Well, I know the month is almost over and I haven't sent u the required amount of videos..."

"Yeah, u have to send me at least one more...But no pressure, it doesn't matter when, as long as it's until the end of the month! u have like a week left..."

"I know, I know...the thing is, I-I can't record myself masturbatin! I can do it, of course, I just can't bring myself recording it...I feel exposed; I don't feel comfortable to have that kind of footage around the internet...Is-is that a problem?"I ask with puppy eyes and bitting my index

"Well...it's the most important video, so it kinda is...but if u can't do it, if u don't feel comfortable, I can't pressure u!"

"Is there any other way to make it up to u? I could send u more of me stripping, maybe? I'm pretty good at that, right?"

"U're great, yeah, better than I thought, but...*thinks about it* I can only think of 2 possible solutions..."

"Tell me!"

"Ok...1. u do it live, in a video call like that, or 2. we meet in person and u do it..."

"Shit...ok...I think I can do the first one? it would be too weird if we meet in person..."

"Whatever makes u feel more comfortable...I don't have a right to record anything, so u just do it and then it's over..."

"Right...will...will u be masturbating too? I guess that's whats u do with everything I send u, right?"

"That's what I do, yeah...so most probably I will be masturbating too..."

"Ok...can-can I think about it? Weigh my options?"

"Of course! I just want to remind u that there's no reason to be shy with me...I think we're way past that!"

"Of course we're past that, u've seen my nudes and stuff, but..."

"But?"

"I've only been intimate with one guy, then I was single for like 2 years and now u've seen more of me than my boyfriend..."

"U...haven't done it yet with Olie?" he asks and I look away

"Felicity...talk to me..."he urges me and after I sigh I look at him

"No, we haven't done it yet...at first it was too soon for me, but after 7 dates I kinda want to...and I know he wants it too, but he must be afraid to ask and I'm too shy to ask..."

"Shy? It's sex...everyone is doing it! Maybe u just don't feel like doing it with him?"

"No! I so feel like doing it with him! I just want him to take the first step towards it, not me..."

"He hasn't done anything that could lead there?"

"He did but I kinda stopped it..."

"How do u expect him to take the lead if u stop him?"

"U're right...I'm the one who told him that I wasn't ready and then I just jumped out of the car..."

"May I ask why u did that?"

"I don't know! Maybe because he's older than my ex? "

"U feel weird that he's older?"

"Kinda...I mean, he has been with a lot of other girls my age and he keeps saying that he feels so different with me, but I'm afraid that I won't be as good as the previous ones...I think I have actually forgotten how to have sex with another person!"

"Don't be silly, u can't forget that! I can't understand how a girl like u had only sex with one guy..."

"Well, it's complicated...we met in highschool, he was in 10th grade when I was in 9th, so he left for college when I was about to be a senior. We tried to keep a long-distance relationship, that's when I mastered the art of masturbation...he kept finding excuses not to come, and that continued for like a year..."

"A year? U lasted a whole year like that? That wasn't even a relationship!"

"I know, I was in love and a fool, we were together for 3 years, I didn't want to believe he would actually forget me when he left! One day, we had arrange for me to go pick him up from the airport, but he never showed and when I called him, he was like Yeah, sorry, I decided not to come! And that was it...then I was very into my studying for the SATs, after that I spent the summer with my friends and then I came here, so I didn't really had time or the energy to find someone...and I'm very sentimental, so having meaningless sex with someone wasn't an option..."

"What an ass...I can't believe he had u like that for a year!"

"I know right? I can't believe I stayed...I still regret staying faithful! Who knows how many girls he banged..."

"Don't think about it! It was too long ago...just move forward!"

"U're right! I will move forward...I will have sex with my boyfriend on our next date!"

"That's the spirit!"he says smiling and I chuckle

"Anyway, I should probably hang up...thank u for everything, I'll let u know about the thing we discussed... "

"I'll be waiting..."he says and then we hang up. I think for a minute what he said and then I decide go to talk with Nicky...