My Promise to Squirt for Dan

This story is 70% true. In real life, Danny and I spent a weekend at his apartment doing molly and he never asked me to promise him what's detailed in the story. Instead he asked me to promise him to "never leave him" but I didn't find it particularly exciting to write about being under the influence of drugs. A lot of the sex scenes are combinations of different dates we had during the time we were a couple. My feelings for him are 100% accurate and most of the sex descriptions did happen but not all in one night. Here's the story;

"Want to get naked?"

That's how it usually started on the weekends with Dan. I'd be sitting on the sofa at his apartment and he'd be sitting behind me with his arms wrapped around me, playing with my nipples underneath my Hello Kitty t-shirt. By this point I was comfortable enough with Dan that I dressed up in girly clothes (at his request) for the majority of the time I spent in private with him. He'd often buy me cute outfits or girly pajamas every other weekend for me to wear at his place and that was something I looked forward to after my college classes. On this day, I went totally casual with my girly T-shirt along with pink yoga pants and plain white boy-shorts panties underneath. My shirt was short enough to leave my belly button exposed and as we cuddled on the couch, Dan would rub my tummy and slide his hands into my shirt to play with my nipples. He liked rubbing my underarms too, which I thought was kind of gross but I guess he appreciated how I shaved them and he actually told me my armpits were a turn on (true story). He was always so gentle and loving and he let me suck on his finger while he kissed the back of my neck. His other arm held me tight against his body like a seatbelt and he seemed to focus on my nipples while I continued to suck his finger, giving him a preview of what I would do to his cock. I could tell he was getting turned on as I felt his familiar bulge pressing against my lower back. I'm pretty sure he was intentionally letting me know how hard he was.

We must've been cuddling and fooling around for a few hours because the movie we were watching was now at the end credits. That's when he asked me if I wanted to get naked and quite frankly, it was the words I was waiting for.

I got up and took off my t-shirt and stretchy pants and removed my panties in front of Dan, completely exposing my hairless body. I took care in removing my body hairs and most of the time, the only hair below my neck was a small strip of pubes about a centimeter wide above my cock, next to my small butterfly tattoo near my pelvis. On this day, even that strip of hair was totally shaved off and I was completely smooth and eager to show Dan.

"Come here cutie pie," he motioned for me to sit on his lap again.

We got back in the same position as before, his arms tightly wrapped around my tummy and I reached for his hand to suck on his finger again. Dan began playing with my cock which he called my "clitty".

"Can you promise me something Jamie?", he asked.

"Uh huh," I said to him with his left index finger still in my mouth.

"I want you to promise me you'll squirt for me three times tonight," Danny said to me as he kissed me on my cheek. "Can you make your clitty squirt sperm for me baby? Three times?"

I turned around and gave my Danny a peck on the lips. "I promise," I said to him, not knowing if it was even possible.

Dan reached for my limp cock and began playing with it. "Promise what?" he asked.

He began to stroke me faster and I could feel my dick getting harder. I looked Danny right in the eye as he continued to stroke my cock which escalated quickly into him jerking me off. His other hand rubbed my tummy as I tried to do my best to flirt with him.

"I promise to make it cum three times for you tonight," I said to him in my flirtiest, girly voice.

"Do you pinky promise? I want to make my cutie pie feel good OK?" Dan reached around with the hand that was on my tummy and extended his pinky. As he did this, his other hand jerked me off faster and faster, but never rough or uncomfortably.

I wrapped my pinky around his and said, "I pinky promise."

My mind was starting to go blank and I began breathing heavily due to Danny's kisses on my neck and getting my clitty stroked by him. As soon as his lips touched my neck, I felt my naked body erupting in an orgasm and my clitty shot out streams of cum all over his hands and on the couch. I let out a few feminine moans and cries and my body began to shiver and tense up. Dan squeezed my body firmly with his sexy hairy arm as his other hand still maintained a full grip around my small but plump cock and squeezed the last drops of semen out of me.

Dan got off the couch and onto his knees and put my penis in his mouth. He cleaned up all of my remaining love juices with his tongue and kissed me again, telling me how good I tasted, which made me blush. I had such a big orgasm that I suddenly felt worried that I wouldn't be able to fulfill my promise to him but Dan was my man. I trusted him with all my heart and I knew he would know how to make me squirt three times so that I would be able to fulfill my promise to him.

Dan got undressed and was fully erect as he escorted me to the bedroom. Seeing my Danny so turned on was extremely flattering and made me feel loved. I often wished that I was a girl so that I could have his baby and we could get married. We had a 30-year age gap but that didn't matter to me and I truly enjoyed every minute I spent with him. He was my first love, my first boyfriend and the man I lost my virginity to, five months prior. Today, he would be the first man who would make me cum three times.

When we got to the bedroom, he led me straight to his king bed and I ended up on top of him, facing him this time. I kissed his muscular chest and his cute, hairy pot-belly. I worked my way down to his hard, warm penis which I teased with gentle innocent kisses, up and down the shaft. I put the entire thing in my mouth and began making love to his cock with my mouth. Every now and then I would look up and see Dan looking at me as he gently put his hand against my face.

"I love you cutie pie," he said to me as I sucked his dick.

I tried to tell him I loved him too but my mouth was full and couldn't speak coherently. He understood what I was trying to say. We had a connection like that, where we telepathically knew what the other person was thinking and we didn't always necessarily have to say it. I wet my lips and deep throated my man all while massaging the underside of his cock with my tongue and let him know I loved him too, without exchanging words.

After about 10 minutes, I pulled his erection out of my mouth and we embraced and kissed. I loved his kisses. His tongue always felt so comforting and seductive at the same time. When I gave Dan my first blowjob, I remember he kissed me afterward and while I never got to tell him, that meant the world to me at the time. I've always had this insecure, illogical fear that guys would leave me after giving them what they wanted because that's what douchebags would do, at least so I imagined. Not Danny. He always kissed me and hugged me after blowjobs to make me feel wanted and not like some cheap whore.

Danny gave me another peck on the forehead and said, "you promised remember? I want to make it squirt for the second time."

Danny flipped me around and lay me flat on my back as he crawled on top of me and spread my legs open with both his hands. He felt heavy and I felt his strength overpower me as I let him do what he wanted with my body. I reached for one of his pillows and held it tight. I knew Danny was going to make me feel intense in a short moment. He usually did. I was ready.

Danny held my hand as he began to kiss my thighs and he said to me in his sweet talk voice, "I want you to squeeze my hand when you're about to squirt OK, cutie pie?"

Before I could answer, Danny was giving me a blowjob, occasionally kissing my balls and even putting his tongue into my pussy. I moaned in the girliest way possible as I often felt much more natural as a girl than a man. Sex has a way of bringing out one's "true" self and my true identity was as Danny's princess.

Dan always made a lot of slurping noises when he would go down on me. Between that and my feminine moans, we probably made a lot of noise, but who was listening? Soon, he was fingering my pussy as he was sucking on my clitty and my eyes rolled into the back of my head. His hand was still interlocked with mine and was waiting for the signal. He was clearly determined to make me cum with his mouth and I didn't hold back. The man of my dreams was making me melt and I was ready to explode again. I squeezed his hand as tight as I could to let him know I was about to squirt and he accelerated his bobbing movements on my cock, which was now a full 5" and totally hard. My moans turned to cries as he pinned me down, just as I began to squirt my juices into his mouth. His pace slowed down and he took every last drop into his mouth and he pulled his finger out of my ass and scooted up to kiss me with a mouth full of my own cum. It wasn't that much. My first orgasm earlier probably had emptied most of it out but I could still taste the distinct flavor of semen in his kiss.

He pulled away and reached into his nightstand for the lube that we kept in there. I was still in a daze, laying there in bliss and without much thought but I was conscious enough to notice he was rubbing lube on his cock. He moved in to kiss me one more time and said, "do you think you can still keep your promise?"

I wasn't too sure. "I'll try my best Danny. I'll try my hardest. I hope you know I'll do anything for you"

"Anything?" He inched even closer and kissed me again on the lips.

"Anything baby," I said, still slightly out of breath from my second orgasm. I wasn't too sure what was about to happen but I trusted Dan, more than I trusted my abilities to reach orgasm for a third time.

It was that moment when I felt Dan's rock hard penis press against my pussy hole and I relaxed as much as I could to take him in. He then made eye contact with me and said, "I want to try get you pregnant tonight."

I felt like such a girl and so honored to know he felt that way. Of course, we both knew I was a boy so getting pregnant wasn't possible, but I remember thinking about how wonderful and intimate couples must feel when they try to conceive.

Danny's cock felt warm and the abundance of lube made it feel wetter than I was normally used to. I grabbed my pillow and used it to mute my uncontrollable moaning and crying. I frequently cried during sex. It's a very peculiar thing, but the best way to describe it is an overwhelming rush of emotions from being penetrated in a very sensitive area by your lover. It's breathtaking, overwhelming, slightly painful and extremely enjoyable at the same time. It's also the idea of sharing my body and feeling a man's erect penis in my most private areas that somehow makes me tear up. I've grown used to it, and nowadays, I tell my hookups beforehand so they don't get surprised by tears rolling down my cheeks during sex. With Dan, however, this was still rather new and even though, by this time we had sex many times, I felt embarrassed about the uncontrollable tears. It didn't bother Dan. His 8" cock pumped in and out of my body and my belly awaited his hot sweet sperm.

As Dan fucked me, I tried to hide my face with the pillow to hide the tears running down my cheeks but he calmly took the pillow and wiped my tears with his thumb. I took his hand and began sucking on his index finger just like the way we started out this whole session. "Cum inside me, please," I pleaded.

"Only if you fulfill your promise, baby," he reminded me.

Danny's cock was now pumping at max speed. The abundance of Astroglide lube was causing my pussy to make a lot of wet sex sounds as his cock slipped in and out of my body. It definitely was a turn on and I started touching myself, trying my very best to cum for the third and final time. It wasn't easy but I knew I could do it. I wanted to do it for Danny.

Dan slowed his pace and asked me to tell him when I was about to cum. I told him I was close and that I wanted him to watch me ejaculate for him. It was in that moment, he pulled out of my butt and finished me for the third time again, in his mouth. He moaned in satisfaction too. He looked up at me, and without saying a word, we embraced in the most passionate, romantic kiss a femboi could wish for. Our tongues locked and I closed my eyes, letting my semen flow from his mouth into mine. He slipped his erection back inside of me and we made out and had sex until he came inside me. It didn't take long for him to squirt inside me. While I can never feel a man actually ejaculate in me, I knew this one was big because Danny grunted for much longer than usual and squeezed me much tighter than he normally would. He held me in his arms and I held him back close to me as his cock got softer and eventually slipped out of my worn out pussy. Sperm leaked out of me onto his bed but neither of us cared. He caressed my tummy like we had just attempted to have a baby and I told him how much he meant to me. I had spent my first nineteen years trying to date girls and never knowing what sex or love felt like, but in that moment I was certain that I was gay and Dan was the man of my dreams. We fell asleep shortly after, both totally spent from fucking.