Author: NYChiefan

Life ✍️ Drawing (Part Two) (M)50 (F)48,21,20.

She raised her eyebrows as if to say I’m not even sure I’m capable of that, and shook her head. The class continued to draw as my hard on raged. After a couple of minutes Professor Raymond said “Okay class let’s get cleaned up and get ready for class tomorrow night and of course let’s not forget to thank our model.”

The class clapped and the big-titted girls friend yelled out “bravo”. The big titted girl clapped politely and smiled demurely. Professor Raymond motioned for me to put on my robe. I stood up making sure I cinched the robe tightly around my cock so it was held tightly against my belly. As the class began to file out the big-titted girls friend made her way over toward me.

“Hi I’m Lynn and this is my friend Penny”. she said “Hi” I said “I’m Tom” I shook Lynn’s hand as Penny edged her way closer to me. Penny continued to speak for the two of them “I can’t wait to see you tomorrow, you were great tonight”. I nodded my head and thanked her and then I looked slyly toward Penny and said “nice sweater.” Read more »

Life ✍️ Drawing. (M)50(F) 48,21,20

I married as a virgin at an early age. My wife had a fierce body and was more experienced sexually than I was. She was hot and loved to fuck but was a little small in the breast department. Unfortunately our marriage soured and we ended up in a divorce.

I had to admit I was a bit depressed when I received a call from one of my wife’s friends, Professor Raymond an art teacher at our local college. She told me she was sorry for my divorce and asked me if I’d like to pose for her Life Drawing class.

“Come on” she said ‘it will get you out and about and it will be fun.” I agreed and then she explained that Life Drawing was posing nude while the students draw you. I had to admit I was intrigued. Professor Raymond was good friends with my wife, cute and I’d always admired her rack at various parties.

“Okay it will be two one hour sessions on Wednesday and Thursday nights starting at 7pm it pays a minor stipend and get here a little early.” I had to admit I was a little nervous but also intrigued. She and my wife were close and I had always thought she liked me. Read more »

The Caddy, Conclusion (M)18 (F)32EE.

After I said this Julie began to grind her ass on my cock and I could feel her knees weaken. Breathlessly she said “teach me this shot.”

We took a couple of practice swings and I told her to hit a couple of inches behind the ball and make sure to follow through. I then removed my arms from hers and placed them on her sweater. I caressed her tits with my hands and she turned around and kissed me passionately. She began to French Kiss me and then broke it off.

“I want to make this birdie” she said excitedly. “Go in the trap, get your stance and dig your feet in the sand an inch or so.” I explained. She did so and then I said “trust yourself, execute the shot.” She gave me a wink and then swung the club as I said she should and the ball landed and skidded right next to the hole. Read more »

Virgin Golf?️‍♂️Caddy(M)18(F)29 Well-Endowed.

It’s funny the next week in school I had a new found confidence with the girls and I got the phone number of a cute girl, but what I was really focused on the entire week was Julie. I arrived early at the club on Saturday morning not knowing what time Mr. and Mrs. Clark were going to be playing.

The caddy master saw me and told me “kid do me a favor and go home.”

My heart sunk. But he continued “But come back at 3:30pm Ms. Clark is playing as a single and she has the last tee time of the day and for some reason she requested you as her caddy. First off she never plays without her husband on the weekends and second why the hell would she request you?” He laughed “Either way be back at 3:30pm and have her bag ready.”

My spirits lifted and my cock hardened. She was playing alone and she had asked for me, I was wondering what she had in store for me and just how she was going to store those massive titties of her’s when on my way out of the caddy shack a couple of the older caddies grabbed me. Read more »

Caddying (Part Two) (M)18(F)30 Sweater Stretchers

After her tits came to a stop she bent over the hole to retrieve her ball and for the first time I really noticed how tight her ass was. You could crack walnuts on the damn thing. Hell it looked like I was going to have a hard-on by the second hole. She got the ball out of the cup and gave me a high five. “Hon” she said to her husband “Let Tom read your putt.” “Ah, no” the old man grumbled and ended up missing his putt badly.

We played the next couple of holes without incident and I tried to pay as much attention to the old man so I wouldn’t get in trouble with him or the caddy master. We got to the fifth hole and Mr. Clark picked up his ball early. While Julie was about to putt he said
“Hurry up, dear I want to get back to the clubhouse and have dinner.”

“All right” she said “I just want to make this putt. What do you think, Tom”? Read more »

I Never Thought Caddying Wood Be So Much Fun. (M) 18 (F)36,DDD

Like any other kid, all throughout High School I was always out of money and completely undersexed. When finally during the spring of my senior year my father helped me land a caddying gig at the posh Country Club near where we lived. My first weekend there I didn’t even get out on the course and made no money. I told the caddy master prior to leaving on Sunday “I know the game well”. But he told me “Kid, you’ve got to pay your dues, maybe next weekend”.

The next weekend was cold and blustery and I figured that meant some of the regular caddies would stay home. Unfortunately that also meant a lot the golfers stayed home. I decided to wait it out (what else was I doing to do, go home and jerk off). I played some cards with the other caddies but there was enough play where soon enough I was the only caddy left. I was contemplating going home when the caddy master came inside the caddy shack. He looked around for one of his more experienced caddies and said “Shit are you the only one left?” “Seriously, I’ll do a good job” I said. He thought for a second and then said “I guess I have no other choice. Here grab the bags for Mr. and Ms. Clark and kid, don’t fuck this up. Mr. Clark is the president of the club and Ms. Clark, well…you’ll see. And try not to stare at her tits okay”. He added “And the way she looks today, it’s gonna be tough. Hurry up I gotta go jerk off in my office.” “Okay” I thought, my dad said the caddy master was a little off. But at least it was a chance to make some money. Read more »

The Librarian (Conclusion) (F)(M) Boobs

“Pretty sure”?, I inquired. “Yeah after I saw him I made my way over to the stack of books where he was standing and I’m pretty sure I saw a significant load of cum on some of the books. There was no way I was going to clean that up, but yours, I will.” Beth then started to loosen my jeans. “I want to see it,” she panted. I slowly pulled my jeans and briefs off and my cock sprang out, alarming Beth. “Oh my god… that’s huge.” she exclaimed. “Can I touch it?” “Of course” I stated “what’s mine is yours.” Beth reached out and grabbed the shaft of my cock and put her hand around it. Or at least tried to. “Oh god, I didn’t think I could fit my hand around it and I can’t.” looking at my cock mesmerized. She ran her hand up and down my dick. “What is that thing gonna feel like inside of me?” she inquired. As she said this she began to loosen her skirt and then quickly removed her from what I could see drenched panties. She then sat back down on her chair and leaned back. Her pussy was glistening and she gave me a come hither look. “Go easy at first, okay” she cooed. Read more »

The Librarian Part lll (M)(F)Big Knockers

NIGHT FOUR:

I was excited to go to the Library the next day and had a hard time keeping my hands off of myself thinking about Beth. But I also knew that I wanted to blow some major loads on her tits later that night and kept myself occupied throughout the day. I held off going to the Library until 8pm and when I arrived I took my regular seat. The old Librarian was working the front desk but was arranging her belongings and getting ready to leave when Beth came from out from the back room and exchanged pleasantries with her. She gave Beth a gift, they talked for awhile and then the older Librarian departed. Beth was wearing her old coat and although she briefly took notice of me she seemed to pay me little attention otherwise. Perhaps, I thought she was upset that I had arrived late. Read more »

The Librarian. Part Two (M)(F) Busty Women

and I think Beth saw me do that. “Hey it’s good to see you again” I said striking up a conversation . At this point in time there was no way I could hide my bulging erection so I decided to stay seated. “Yeah you too.” Beth chirped excitedly. “Hey it’s pretty close to closing time did you ever get that Library card?” Beth asked. “No I’ve been busy” I lied. “Well let’s get that taken care of right now, come with me.” Beth waited while I put my things together. I looked over briefly at her which didn’t help my erection which was actually beginning to protrude out of the waistband of my jeans. I figured Beth being the shy demure Librarian that she was would (even if she noticed my erection) look away in embarrassment . As I nervously stood up I locked eyes with Beth and smiled and reached into my my jeans to re position my cock to the side. But Beth’s eyes did indeed travel downward and I was pretty sure she could see my straining erection in my pants. I tried quickly to pull my own sweater down to cover myself and meanwhile Beth had raised her left hand to her mouth in order to stifle what I figured was the shock of seeing the sheer size of my cock. I knew she had caught a glimpse of my huge bulge. What Beth didn’t know (at least until this moment) was that I too had a large endowment of my own measuring at a thick meaty nine plus inches when erect (which I was now) and almost as thick as a soda can. Read more »

Not A Breast Reduction! (M)(F) Large Breasts.

I had invited my girlfriend over to my apartment for the first time recently. We were new to the relationship and I had been on my best behavior throughout. At the time she arrived I was watching my favorite college football team and was into the game when she cuddled up next to me on my couch. I could tell something was on her mind. I asked her what was wrong “I’m seriously thinking about getting a breast reduction.” she said. Hold the phone, I thought, College Football could wait. “What do you mean” I asked her. “Well just this past week I had two incidents where my boobs got in the way of what I was doing.” I was intrigued and asked her to continue. “On Tuesday I was shopping at a department store and I knocked some clothes off of a clothing rack with, well… my rack! A salesman was watching and I could tell he had never seen anything like that before. He was nice and everything and we got to talking and he asked for my number. Of course I didn’t give it to him but the whole situation was embarrassing.” My boobs just keep getting in the way .” Being the good boyfriend I pulled her closer to me. . Read more »