Her 1st orgasm to pillow princess [FM]

Shoot. Should be [MF]. Sorry to anyone who clicked thinking this story was from the woman’s perspective. But reddit doesn’t allow editing of titles.

In my late twenties I decided to pivot in my career. My new path required grad school.

In researching the career and schools, I found there were message boards filled with people like me applying to the same type of program.

I made a few friends on there and when several of us ended up deciding to go to school in the same city (though not all to the same school), we all met up for drinks during orientation week.

Jen, who went by the username hotgradchick, and I had flirted a bit online in the months leading up to school. But I had a girlfriend, and had never cheated, so we never crossed a line. 

This was pre-social media, and most people only had one or two scanned photos they could share. So I could tell is that Jen was cute (cutegradchick would have been a more accurate description), but I was not prepared for the sexual chemistry I would feel when we met in person. She was 24 with a cute face, small breasts (B cup), a tiny waist, wide hips. She had light brown hair, was about 5’2″ and had a great ass. 

The first time we all met she was wearing a tight shirt, jeans, and heels. I walked her to the train from the bar and was hard the whole way. I still had a girlfriend and didn’t do anything. 

Jen and I became good friends during the first semester. She went to a different school, but we lived near each other. We were both far from home. I was from the West and she was from the South. Not just the South, but the country South. No Southern Belle accent, but a country southern accent. I loved hearing her talk. 

She shared with me her dating woes. At some point she opened up and told me she had never had an orgasm. 

Despite a bad start to my sex life in the early years, by this time I had actually gotten pretty good at helping women achieve an orgasm. 

I gave her some suggestions, such as just touching different parts of her body for five or 10 minutes each night. Caress herself, her breasts, her thighs, etc. To not do it with any intention of orgasm. Just to touch and see what feels good to her. And then to try touching her pussy in different ways, again with no expectation of orgasm. Try rubbing above the clit, rubbing her lips, trying fingers inside and outside, and just see how it feels. 

It didn’t work for her. She had sex with a couple of guys that semester, but with no orgasmic success. 

My girlfriend stayed back home, we were from the other side of the country. She planned to move to join me after my first year. 

But I broke up with her over winter break. I just couldn’t ask her to move across the country when I didn’t see marriage in the future. 

Jen was my friend, so I told her about the break up. We IM’d on AIM often. We were grad students with laptops always with us and wi-fi was pretty new. She mentioned another failed encounter with a guy. Well she wasn’t sure if it failed. She said she might have had an orgasm. I told I her I was pretty sure that if she really had an orgasm, there would be no doubts. So that she likely didn’t.

We were on AIM a few days before I was to come home from winter break and I was again, unsuccessfully trying to walk her through it. Then we got on the phone. I was so hard knowing that she was touching herself while we talked. Not only touching herself, but her hands and fingers were doing whatever I directed them to do. 

She said it felt good, but did not think she was going to cum. I told her not to think about cumming, just to enjoy her body. She asked if I was turned on having this conversation. I told her she turns me on all the time. But that yes, hearing her southern drawl and knowing she was touching herself, I was so hard. 

She asked if I was touching myself. I told her I was. Then she started telling me what to do with my hands. This has quickly turned into phone sex. Or was it phone sex from the start? 

She had me stroke myself slowly and softly. Then fast and hard. Then had me stop stroking and instead playing with my balls. I’d asked her to play with her nipples before, so she had me play with mine. Then she had me stroking again. I told her I was close to cumming and asked if it would be fair that I would cum and she wouldn’t. She said, “Cum for me, now.” So I did. 

That was so hot to me.

At some point that night or the next day one of us proposed that maybe I should try to help her in person. I explained to her that even though I just broke up with my girlfriend, we had been together for three years and I wasn’t sure the break up would last. I told her I didn’t want to have sex with anyone for a few months until I was sure we’d stay broken up. I didn’t want to have a whole “But-we-were-on-a-break-issue.” I said that I enjoy eating pussy and I would come over anytime she wanted me to do that. 

I told her I loved giving a woman oral so much that I didn’t care if she came and didn’t expect that she would. And she should not expect to cum the first time, or maybe even the first few times, if there was more than one time. She should just enjoy the feelings and discover what felt good to her. I was pretty confident I would make her cum, but wanted to help her anxiety so she could relax and enjoy.

I asked if she was shaved or waxed. She said trimmed. I asked how trimmed. It didn’t sound like it was very trimmed. Just bikini line. 

I told her I would only do it if she shaved or waxed. I was kind of bluffing. I really prefer having a clean palette to work on and hate getting pubic hair in my mouth. But if she had declined, I probably still would have done it.

She hesitated at first. While she was no prude and had fucked several guys in her life and had no reservations about an occasional one-night stand, she was still a small town girl and going hairless seemed weird to her. But she agreed she’d shave completely. 

It was cold and snowy the night I got back from winter break. I got home around 9 p.m. I talked to my roommates. Unpacked. Got in bed and opened my laptop around 10. She was there on AIM. We chatted a bit and then she asked if I was serious about what I said I would do. I played dumb. Made her say it. And then said I would eat her pussy any time she wanted. She asked, “now?”

I bundled up and walked the five blocks to her apartment. She buzzed me in and I walked up the three flights of stairs. When I looked down the hall toward her apartment, she was standing in the open door wearing a thin, short pink robe that was loosely tied. 

There would be no awkward chatting and sitting around wondering who would make the first move. We kissed in the doorway as her Golden Retriever barked and jumped from the closet. 

She lived in a small studio and had a big dog. She had a baby gate on the door of the large-ish walk-in closet and had Mollie, the dog, in the closet. Watching us. 

We shared a hot kiss and then looked at each other, smiled, kind of laughed. I pulled her robe open and then lifted it off of her. She was wearing nothing underneath. I stood back and looked her over and told her how sexy she was. We worked our way to the bed and I laid her back. I was still fully clothed, I had only removed my jacket and shoes. 

I kissed her mouth again. Then her ears and neck. Licked and sucked her nipples. Told her how great her tits were and how I loved her small nipples. Kissed down her stomach. Went right past her pussy and down her inner leg. I was slow. I told her how much I enjoy this and thanked her for letting me. And that I hope she would enjoy it also. Her body was telling me she was really enjoying it. As were her soft moans and increased breathing. 

I kissed down to her foot and then switched to the other foot and worked my way back up. When I got to her pussy I spent several minutes kissing all around it, but not coming in direct contact with any part of it. 

Starting at the bottom, I lightly licked her lips. My tongue just barely penetrating them. I stopped for a second, looked up at her (damn she looked sexy from this angle) and told her pussy tastes amazing (which was true). Then I licked up to her clit. I just lightly flicked her clit with my tongue. Then I licked her lips a bit more. Sucked on one before working my way up again. I pressed my tongue more firmly, right above her clit. Not making direct contact. Her hips started to slightly rock. 

I usually enjoy teasing and edging a woman a few times before letting her cum, but I wasn’t sure that would work with Jen. I was afraid she’d get close, not cum, and then get discouraged. So I decided to let her cum right away. I pressed my mouth firmly on her clit, sucking it into my mouth and then flicking my tongue against it fast and hard. 

Her hands grabbed the back of my head and her hips began bucking. Her breathing was heavy and then her whole body tensed and she screamed “FUCK!”

She flinched with the next flick of my tongue and I knew she was too sensitive to continue. Her juices were everywhere. I just spent a few minutes licking up every drop and then sliding my tongue deep between her lips. 

“I can’t believe how amazing you taste,” I told her.

Finally, I lifted my head up. She looked so sexy. She looked exhausted. She was sweaty. She smiled at me and said, “Holy shit. That is what I have been missing?”

We cuddled and kissed a bit and talked about the experience. She was really happy yet in a state of disbelief. How did I do in 10-15 minutes what she had never been able to do alone or with another partner, she asked. I told her she just needed to relax.

She said now that she had experienced an orgasm, she was certain the previous experiences were not orgasms.

She asked if I needed her to help me cum. I reminded her that tonight was just about her. There would be plenty of opportunities for other things. Then I went back home. From leaving my bed to returning to it was less than an hour

Source: reddit.com/r/gonewildstories/comments/xf57am/her_1st_orgasm_to_pillow_princess_fm