The Sugarbaby Chronicles

I never thought I would find someone so mature and exhilarating. I've dated men that were fun and I could go out with, but never one that made me feel adventurous and trust them in any situation and outing. We met online and talked for a week. That was the quickest I've given out my number and shown my erotica. Normally, it would take at least 2 weeks to ensure I wasn't simply wasting my time on someone else who just wanted to sext or ask for nudes. He read my stories, looked at my pictures, and knew we were compatible. This is important as what lived in his fantasies matched mine to a degree.

What really piqued his interest beyond being curvy and loving to dress up, were my orgy/group stories. I've only been monogamous and those were fantasies just for the sake of writing. He asked if I would indulge him in having sex with other men while he watched. Sometimes he would join in, even cam. I was hesitant at first because of a few factors, but he assured me it would be done on my terms, and he would always be there to look after me. We went out a few times before deciding on how to meet partners, where to go, what to wear, and how each meet would work.

We shopped for all sorts of things both cliché and ordinary like French maid and schoolgirl costumes, high heels, corsets, toys, and jokingly referring to me as sugar baby, and he my sugar daddy as he was 10 years my senior. He mentioned even my makeup being dark and intense to match it all. I became more and more excited as he described parties at lovely Air Bn' bs, getting a room for our smaller last-minute rendezvous, wanting to see others enjoy me as much as himself in my outfits, and making our own private collection of photos and videos.

He wasn't bashful and every time I shared new thoughts about what we would do upon meeting couples or other men, he would grow, strip us both and take me on the spot. This made him impatient too and asked when we would have our first get together. I thought about the best way to find people, and remembered seeing couple profiles before. I set one up discretely and joined more erotica sites to find the best fits. Like dating, I couldn't just invite anyone into our lives. They had to be witty, experienced, a little romantic, and accommodate some basic rules.

After some difficulty finding good matches, our first weekend was rolling around and I wondered what the angle would be. He did know how to spank me just right and it was the one thing I wanted him to do after kissing me every time we saw each other. His hands always found their way to worshipping my ass with a squeeze, jiggle, spank, then followed by rubbing his short whiskers, and giving it a bite. This inspired me to make it the theme of our first group night. None of my previous partners wanted too much if any foreplay, but he agreed there should be a lot of it to make the best experience. I wanted to try my hands being tied up, and be a little exhibition, just for starters. I told him about how I want to be tied to the headboard by my hands, sitting on my knees, and he would teach the others how to treat my ass. Intrigued by this idea, he asked many questions and I answered them all with him now organizing what he would say and do in his, "role".

He gets a room downtown and sends me the address. I send it to the guys and then finish getting ready, grab my purse and other bag, then head on my way. When I get to the room, I see he's pulled back the curtains exposing us to the city. Granted we're 10 floors up, but I relished the idea of feeling open, and the gorgeous view of the buildings, stars, cars zooming pass. He walks me to the bathroom and watches as I get ready. For this, I decided on a dark red and black bustier just a bit small so it pushes more down for them to play with and makes my nipples almost slip out, a matching lace thong, black tights with bows, and suede black high mary jane shoes. After doing my makeup, he takes my hand and walks backwards while staring at me. Every bit of it; the thong, high heels, tights, and bustier are all 4 elements that he specifically loves. Having them all together gave a glint in his eye I'd never seen before. I sit on the bed while he tries to get just the right angles moving his computer around.

We hear a knock at the door and greet them. Like good hosts, we have some bourbon and a glass set ready we brought. The bottle is cracked, glasses poured, and we all chat. Once he gets to know them a bit, we tell them the plan. One of them starts to tie me up as the second and third stand at the end. My boyfriend starts the stream, then acts like a good spanking instructor. He covers the cupping of the cheek after spanking, how far back to bring their hands, and intervals. He grabs the thong and pulls back telling me to put it up in the air more. I feel him smack and the cheek sting slightly as it bounces. Through more instruction, he reminds them to evenly treat each cheek making them the same pink shade. I sit there and giggle with each swat. He's a great teacher as each one almost made it impossible to tell they weren't the students after a few minutes.

They take their clothes off and he walks back to the computer. I feel one of them climbing up behind me as the other walks to my side. He brushes my hair back, runs his hand up and down my cleavage, then pulls both breasts out along with his cock. He strokes while playing with the lace. The one on the back alternates between stroking and slapping me with his, and running his other hand over each cheek. The one beside me steps up, over and between my arms, then tips my chin up with his finger, and then pulls my lip down. I open as he puts his head in only and pulls out. A few more strokes, then gets down into my throat. Slowly he bends his knees bobbing in and out while playing with my hair.

I'm getting two holes filled as knuckles starting to penetrate and stretch me out. I start to gag as he's in and out faster, which the boyfriend loves and gets up to zoom in the laptop. A fourth finger enters making the lips sensitive. I take a little break to breathe and he resumes keeping the erection up. When I'm sufficiently wet, I feel a finger in my ass, then it wiggling. The one in front of me steps off to the back of the bed, then immediately shoves in. He doesn't waste any time as he's longer and wants to go right for the cervix. He's steady and thorough just like with my throat. The other one keeps his finger in my tight ass and walks up. He lifts his large, very girthy cock and puts his balls in my mouth. They were also so big I had trouble fitting them in, but I adjusted my tongue and sucked so they took up the whole cavity, then tickled them with the tip of my tongue. Everything had something in it and I couldn't do anything but sit there and take it which felt great because I loved the endurance and attention.

The one in the back gets faster, then suddenly pulls out. He goes to the side and holds in his cum, pulling his finger from my ass to pinch his head. I give one long suck, and he pulls the balls out. He goes to the end and rubs the stockings with the left hand, and I feel it sting as his fat head steadily makes its way through guided by his right. He gives me a few short strokes, then grabs the front lacy top of the hose, rears back and plunges in as hard as he can. I let out a very loud moan as he twist his hips from side to side squishing into me more. He gets on the bed and scoots up on his knees still locked into me completely while we scoot up further together. He gets high on his knees pulling back a few inches, and says he wants me to ride and meet him halfway. It would be easier without my hands tied, but I'm still able to bring myself to raise my hips up and take him in. I look over, and see my boyfriend set the computer down, and unzip. I keep pushing up and he begins to rub himself.

I feel a hand push down on my upper back, and nudge my thighs out. He starts fucking so hard I squeal. Hearing the smacking sound on my large ass makes the bf rub harder. The bustier is restricting me and makes me gasp with each deep, splitting shove. He gives one final blow, then pulls out fast making my pussy feel like it's going to collapse. I focus on getting my breath back as I feel the master back at spanking me again. I look back to see my bf there in his suit, shirt partially unbuttoned, and now finishing me off. He enters and pulls out completely teasing me a little, then gets in and rubs my clit. He wanted to be the only one to cream me that night, but see the cheeks and stocking covered with cum too. I'm squeezing while he pumps and then then he buries in while his finger goes in circles furiously. I give him one hard clench, then feel him shift. He pulls and then the warm, sticky sensation oozes out. The other two come up and spray my backside, and thighs.

They sit down for a minute, get dressed, and we all say how much we want to get together again. Once they left, he leans in, pulls my hair back, and gently kisses my neck telling me how that was so beautiful how I did that for him. After I'm untied, we strip and then get into the warm shower.