Mutual Masturbation Rendezvous

During the summer before my senior year, my Aunt Jo offered me to come stay with her in Pennsylvania because of a great job opportunity. She worked for a finance company and needed someone to work in the office. I decided I could not turn down the opportunity to make so much money, so I went. In late May, I flew across the country from my home in California to live with my divorced relative for a few months. My first day at work is when I met Tyler and we hit it off right away. After some casual flirting, we quickly advanced to becoming an item in less than a week.

During a late June evening, I was at Tyler's house and we were in his room hanging out on social media and playing video games before we started kissing. He was also 18 and like a typical boy that age, he was pressuring me to have sex. A friend of mine had gotten pregnant during our sophomore year and it had terrified me so much that I was really leery about the subject. Even with my reluctance, my own hormones were just as active and I was really curious about other types of sex outside of intercourse.

"Look what I got," smiled Tyler as he held up a packaged condom.

I sighed, "You know my rule."

"C'mon, we have been together a month now and I'm gettin blue balls over here," he whined.

I was wet from our make out session, so I offered, "Lock the door. I will...you know," as I made an open fist and moved it up and down to signal a hand job.

An excited Tyler, jumped up, locked the door and within ten seconds, had his pants laying on the bean bag chair while he laid on his back across his bed. He had a thin, smooth six inch cock leaking all over his belly. Seeing seminal fluid in real life for the first time was stimulating to me. I sat on the bed beside Tyler and jerked his cock while using that leakage as lubrication.

Sliding my hand up and down, I wanted reassured, "Am I doing it right? Does it feel good?"

He groaned, "Oh yea. Do it a little faster. Yes, just like that. I'm going to cum."

Upon request, I jerked faster when Tyler let out a large moan while shooting cum all over his stomach and the back of my hand. Tyler was satisfied as I looked around for something to wipe my hand off with. While watching it squirt out along with feeling it on my skin sent butterflies through my own stomach. It was sexual, different, and once again, exciting. Giving my first handjob inspired me to go back to Aunt Jo's and masturbate for over an hour. It also inspired me to jack Tyler off every single day for the next week. He wanted me to progress to the next step and suck him off but I still wasn't quite ready for that.

That Monday evening, Aunt Jo's company met several other financial firms at a local restaurant for a large dinner. I wanted to look as professional as I could, so I wore a matching pin striped business skirt with high heels loaned to me by my aunt. Following Jo's advice, I also put my long dirty blonde hair up to "convey a serious presence." Ideas, clients, vendors, business deals were all discussed as several dozen of the local business men and women ate, drank and enjoyed each other's company in a private reserved room. Having only been working a short time, I mostly just listened and tried to learn as much as possible.

While waiting in line at the bathroom, one of the business men from our room walked past me, stopped then held out his hand, "Hi, I'm John and you are very stunning."

I smiled, held out my hand and shook John's as I responded, "Thank you. I'm Brittni, Jo's niece. I'm working with her over the summer."

It was obvious John had been drinking when he said, "I mean it. You are very pretty." He pulled out his card and handed it to me while continuing, "Seriously, if you ever need anything and I mean anything, don't be afraid to contact me."

I laughed, "Sure thing John. I don't have a card but my email is in our online directory. It was nice meeting you."

The next day, bright and early at work, I noticed I had received an email from John. He was asking me to lunch in the lobby of a five star hotel located on the other side of town. It was sweet, but I didn't know the guy, he was much older than me, and I had a boyfriend. I respectfully declined as I told him that I needed to get to know him better.

He then continued to email me throughout the day so that I could "get to know him better," and he would ask me questions as well. For some reason, I could not stop responding. Maybe it was because he was an attractive older man that was built well. Maybe I was flattered. Maybe I was just curious.

I did find out he was 38 years old, was single and owned his own financial consulting business which explained why he was at the dinner. He also told me that he was a firefighter along with other personal information. The emails gradually turned from casual to more personal to sexual. I couldn't stop replying as I was quickly getting drawn into this stranger's life. He asked me for my cell number and my intrigue caused me to give it to him.

The first text I received from John was a picture of his cock and it was rock hard sticking straight in the air with the caption, "What do you think of this? It's 8 ½ inches of raw power," with a winking emoji after it.

I was blown away with his brashness but I was not angry. That cock looked huge to me. It was definitely something to show off with the massive thickness to go along with the length. The head was large and I could see all the veins bulging up the shaft even though the lighting was dull. I have to admit, I was aroused by the pic but I was also a little nervous. This was getting so real and I was still a virgin who only started whacking off my boyfriend a week earlier.

John continued to text me and I would respond. He begged for nudes and for some reason, I couldn't say no and later that evening I sent them via snapchat. I made sure to keep my face off the pictures in case they leaked out. I turned down his offer for lunch several times but he was very persistent. I finally agreed to meet him for lunch on Friday because Aunt Jo let me take a half days off on Fridays. He also requested that I wear the same pin striped business skirt and pumps that I had worn at the dinner when we met.

That evening, I was jacking Tyler off in my room when I couldn't help but fantasize that his dick was actually John's huge dong. I was making myself horny from the thought and when Tyler's cum flew up in the air and a glob landed on my arm, I almost orgasmed.

I had trouble sleeping that night and debated with myself if I had made the right decision on meeting John. What if he expects more? What if I can't say no? That dick of his did look amazing so I wrestled with my sanity all night.

When Friday arrived, I finished up at my desk around noon. Per John's request, I was wearing the skirt with the matching blazer. On the drive over to the hotel to meet John, I continued debating with myself with negative thoughts such as, "Brittni, this is how people end up on Dateline," and positive ones such as, "He is a respected businessman and a firefighter in the community." I also had to tell Tyler I was meeting a potential female business client that Aunt Jo requested I see.

I walked in with my high heels clacking on the tile and saw that John had a table for us. He was very handsome and dressed in a suit and tie. We hugged and sat down. During our lunch conversation John and I discussed light topics such as the weather and my home life back in California among other things. Just like with this texts, he wasted no time being bold with his requests.

"You know I think you are so gorgeous. I have a room in this hotel. Would you like to come up with me for a little while? I promise, I will behave," John asked.

I squinted one eye in revealing the truth, "I'm going to be honest with you. I'm still a virgin and have very little sexual experience. I don't know if I feel comfortable."

He reassured me, "Listen, you have no worries from me. I won't try anything you don't want. Why don't we just play with ourselves in front of each other and see how that goes."

I instantly got a twitch in my vagina as that actually sounded pretty hot, so I responded, "Really? We don't have to have sex?"

"Oh no. I have done this with other women and they loved it. You can watch me play with myself and I will watch you. It will be very erotic, I promise you," he seductively explained.

John was actually a year older than my father which strangely turned me on more than if he were my age. He was an adult, a grown up man, very masculine who knew what he wanted and I was attracted to that quality. I agreed to go up to the room with him, he graciously paid the lunch bill, and we soon found ourselves in the elevator heading to his room.

Once inside the hotel room, John took control of the scene, "Britt, you get up on the bed. Leave your heels on because I think that is sexy. Here use these pillows to lean back on the headboard."

Just following his directions, made me wet. I couldn't believe I was actually doing this. He was taking control and my stomach once again had butterflies. After draping his suit coat over the chair, he began unbuttoning his dress shirt exposing his masculine hairy chest. John took off his pants and neatly sat them on the foot of the bed before dropping his underwear to the floor. His large manhood flopped out and was already half erect which looked even bigger in person.

John began stroking his cock while looking at me. He never lost eye contact as he sat in the chair at the foot of the bed. Watching his veiny forearm, jerking his thick dick only added to the eroticism for me.

John smiled and whispered, "You like watching daddy jerk his big dick, don't you baby girl?"

I was mesmerized as I could only answer, "Uh huh."

He continued, "You make it so hard. Look at me jerk it because you are so beautiful. Why don't you pull your skirt up and move your panties over so you can play with yourself for daddy."

By then, my black, lacy silk panties were already supporting a wet spot. I pulled my skirt up to my waist, spread my legs, exposing my covered pussy. I began rubbing my clit through the silky material. It was electric and I almost came just from the initial pressure.

"That's it. I like that. Look here, can you see the precum leaking from the head? That is what you do to daddy. Pull the sexy panties over and put your finger inside yourself," he requested while talking occasionally in third person.

At that moment, I probably would have done anything listening to this man while he stroked his gorgeous dick in front of me. I used my left hand to pull my panties to the side while sliding my right, middle finger all the way inside my gooey slit until it reached my hymen. It felt great and it was like watching and masturbating to the most erotic porn I could have imagined.

Without taking his eyes off me, John stood up slowly, never disrupting his stroking rhythm. Be began to walk to the side of the bed. His hand was moving quickly and the closer he got to the edge, the louder I could hear the slapping sound of him jerking.

"Oh shit, baby girl, you've got that pussy all wet for daddy. See how many fingers you can put in there," and after I fit three inside myself, he added, "Oooo, that's it. Get em in there. Just like that. Take your hair down baby girl and scoot over here. Daddy's gettin close to cumming and I need you for that."

Taking the clip from my hair, I shook my head causing the messed up strands to fall past my shoulders and into my eyes. I was still fucking myself with three fingers and also getting close to cumming. I couldn't believe how erotic the entire scenario had played out.

"Take your panties off and get on your knees here on the bed," John ordered.

I was putty in his hands. It was like I was hypnotized by this alpha male dominance. I slid my panties down but they got hung up around one ankle. I wasn't worried about that as I rose to my knees causing one of the high heels to fall off my foot. John climbed up on the bed and stood in front of me. He was completely naked, beating his meat not more than six inches from my face.

"Fuck, I'm getting so close. Start fingering yourself again. Oh, yea, just like that. Use all three. I know you want this load all over your face. You want daddy's load, don't you?" he mumbled.

Once again, I had no emotional choice but to agree, "Uh huh. I want it bad."

I couldn't believe those words just came out of my mouth but the truth was in that state of lust, I really did want it.

John grabbed a fist full of my hair from the back of my head, holding me steady as he was now furiously jerking off, "Augghhhh, fuck!" he shouted just as the first rope of cum launched out of his cock and landed across the top of my hair and forehead. After a quick adjustment, he aimed slightly lower and the following spurts struck me in the eyes, all over my face and into my opened mouth, "Auggh, fuck yea, take it baby! Auggghhh! Augghhh! Take all daddy's cum. Open your mouth wider. Augghhh!"

When I felt John's warm thick semen landing on me, I immediately had the most powerful orgasm that I had ever had up to that point in my young life. My eyes were now blurred with sticky slime. I could smell the pungent odor of his pent up sperm on my upper lip and I could taste the bitter saltiness on my tongue. I thought he would never stop shooting.

When his orgasmed ceased, I could longer see but I felt him place the head of his cock up against my opened mouth before instructing me, "That was fucking amazing baby girl. You were great. Now clean daddy's cock off so I can get back to work."

I sucked the tip while he squeezed the cum out of the softening shaft. I had never had a penis in my mouth, let alone cum and now I had both. John continued to hold my hair to ensure my mouth stayed on his cock until he was completely finished.

He let loose his grip on my hair, then stepped down off the bed just as I could see my phone buzzing a call from Tyler, "Go ahead, don't be shy. Swallow what I gave you."

I ignored the call as I felt the cum starting to run down my face. I swallowed the spunk in my mouth and with impaired vision, I got up to feel my way to the bathroom. Grabbing a towel off the rack, I cleared my eyes and to my horror, there was so much cum on Jo's pin stripped blazer and shirt that I was sure it was ruined. I couldn't believe he had so much of it stored in those balls and I couldn't believe how I wasn't better prepared. How in the heck was I going to get it all cleaned up?

I wetted a towel and was wiping off my face while pulling globs from my hair. I took off my blazer and shirt and attempted to rub the stains out with a sink full of water. A fully dressed John appeared behind me as I looked at him in the mirror, dressed only in my skirt and bra.

He tilted his head and used it to point, "I'm gonna take off. We should make this a steady thing."

While wiping my face I responded, "I have boyfriend."

He retorted, "That's ok, you are much too young for me to date. You can just be my cum dump when I need it."

With a puzzled look, I asked, "A what?"

"My cum dump. We can just get together for some of these sessions and you can catch my load when I need to release. I really gotta run. I will text ya."

John walked out of the hotel room and left me to clean myself up. I should have been very upset but I wasn't. His cavalier attitude about what had just happened actually turned me on even more. I felt like a prostitute that was just used for a guy's gratification and I enjoyed it. What was wrong with me? By the time I had cleaned up the best I could, Tyler had blown up my phone with several texts. I called him and made up a lie to buy me some time. I stopped at the outlet store, bought a pair of shorts and a t-shirt so I could drop the fouled clothing off at the dry cleaners. As soon as I got back to Aunt Jo's, I showered before Tyler arrived.

I told myself that even as thrilling as the secret mutual masturbation with an older stranger was, I needed to stop, and that it wasn't normal. Over the weekend, I would give Tyler his usual handjob but could not get John and our tryst out of my mind. By Monday morning I still hadn't heard from John, so I figured it was a onetime thing and that might be best. By Monday afternoon, I get a text and another dick pic from John with the caption, "This thing is addicting isn't it? How about we meet the same day, same place at the same time." I wasn't going to answer it so I ignored it until that night. After Tyler had left, I had no choice but to respond with a "k" on the text.

Sure enough on Friday afternoon, I walk in and John was sitting at the same table. We ordered, ate and headed upstairs as the same excited butterflies entered my stomach while we were in the elevator. On that day, I was wearing a collared button up red blouse, a pair of white slacks, with red heels. My hair was down, curled and I wore long, dangling, silver earrings.

When we walked inside the room, John said in character, "Daddy hasn't cum all week. He's been saving it for ya baby girl."

I wasn't going to make the same mistake with my clothing, so I removed it, including my thong. This time, John took the bed and I sat on the chair. I spread my legs and put my knees up so high that my bare feet were braced upon the arms of the chair, giving John a nice view of my smooth, bald pussy. When he removed his pants, he was already fully erect from the anticipation. He was sitting with his legs spread, slowly stroking his big dick while I diddled my already moist slit. Watching his balls shake while he jerked his prick stimulated me even more.

"I love those young, firm tits you got and such a pretty pussy. I like that you keep it bare for daddy. Rub that clit baby girl. Back and forth, nice and slow. Mmmmm, that is hot. Now rub in a circle. Yea, like that. Keep going. Faster," John directed me so to turn himself on.

I warned I was getting close to cumming with all the instructing and visualization, "I'm gonna cum, Daddy."

"Ooooo, yea do it for daddy. I think that pussy needs those fingers again. Go ahead and stick them in there," he whispered. As I plunged them inside my slippery opening, he gasped, "Oh fuck. That's gonna make daddy cum quick. Now lick your fingers. Show daddy how you can swallow your sweet juice."

I was alternating from sliding my fingers inside myself and sucking the liquid off them, causing me to orgasm with a loud moan, "Oooo, I'm cummin! Unnggg!"

Once I started cumming, John immediately slid off the bed and quickly walked to me, grabbing my hair in the back of my head like he had done previously before announcing, "Push your tits together. I'm gonna fuckin blow!"

Like I was wearing a pushup bra, I mashed them together then opened my mouth with my tongue out, awaiting his seed as he grunted like a wild boar, "Shit! Augghhh take that!" as his cum spurted from his cock directly onto my boobs. Not to miss anything, he varied his aim, squirting me in the face, neck, and back to my breasts, "Oh, damn. Take that! Aughh! Yea, take daddy's load, my little cum dump!"

I was a mess again but at least I could see because the cum had missed my eyes. I swallowed what little had entered my mouth while in a flash, John had dressed and left. I was still horny so instead of cleaning myself up, I sprawled out on the bed and masturbated while rubbing and eating the cum off my body. It was so nasty and slutty, I had no trouble getting myself off several more times. When I had finished up, I hopped in the shower then called Tyler and told him that I was on my way. I felt guilty but the sexual bliss I had just experienced was just too powerful for me to stop.

The next two Fridays were similar rendezvouses and both times John unloaded either on my face or boobs or both. He was getting creative and had me in a different positions each time. One of those sessions, I was lying on my back on the floor with my knees up, fingering banging myself while he stood directly over top of me. While straddling my body, he jacked off until his cum fell from above, splatting all over my face. Feeling it hit me from that distance caused me to violently jerk in orgasm.