Fall 2001, 21 yrs. old
The first time someone paid me for sex was quite an experience! After I’d turned twenty-one, I started frequenting Sandie’s regularly looking for the occasional sexual encounter. I enjoyed the company of the other girls, and took a couple back to my place.
I saw Jo there quite often, usually in the company of older trannies. We’d share a drink and chat, but never repeated that one night! He asked me for my phone number and would call to check up on me. He even sent a nice bottle of champagne to my apartment for my 21st birthday!
One evening, Jo brought an older gentleman to my table and introduced me to William. Jo excused himself and left me with William. We chatted a while, then he asked me to dinner. He was wonderful company and treated me respectfully.
He dropped me at my apartment and I invited him up. One thing led to another and we ended up in bed. I lay on my back and let him take me face to face. He wasn’t large, but he fucked me enthusiastically. We snuggled after he finished and I made him coffee. He kissed me goodnight, thanked me, and left.
The next morning, a courier delivered flowers and an envelope. William thanked me for the lovely evening and hoped we might see each other again. The envelope also had two one hundred dollar bills!
I called Jo and told him about the envelope.
He laughed and said, “Many married gentleman would gladly pay for the privilege of fucking a beautiful woman like you! If you wouldn’t mind, I can give your number to a few of my friends. Men you’d be safe with and would probably like! What do you say?”
“I don’t want another pimp!” I exclaimed forcefully. I then told him about Dave.
“Goodness me! I don’t want any money from you! I’m just saying…..if they’re willing to pay you to do what you already want them to do……”
I suspected that Jackie might have been selling her staffs’ favors. But we were well compensated weekly, so I didn’t mind as much. I agreed and Jo said he would set me up.
Almost two weeks passed before I got a call. Gerald asked to meet and I suggested Sandie’s. He looked nice, maybe in his late fifties. He kissed my cheek and bought drinks. We visited then went to dinner. (I really didn’t care if anyone paid me. I’d spread my legs for any man who took me to a nice restaurant and treated me decently.)
After dinner, he drove us to a local lover’s lane overlooking the ocean. We sat in the backseat and kissed a while. I straddled his lap, pulling my panties aside and guided him into my ass. He fondled my breasts through my blouse as I rode his nice cock. Gerald lasted about fifteen minutes. I let him stay in me a few minutes, then moved over. I leaned over and took his cook into my mouth.
I slowly bobbed up and down his shaft and lightly stroked his balls with my nails. He slipped a hand inside my panties, caressing my bottom. He soon filled my mouth with his salty cum. I raised up and smiled.
He drove me back to my apartment and I invited him up. He was surprised, but readily agreed. He couldn't get out of his clothes fast enough!
I lay on my back and let him enter me. I wrapped my legs around his waist, drawing him deeper. His cock felt nice sliding in and out of my channel. I raked his back with my fingers, avoiding using my nails: he hadn’t hid that he was married from me. I held his head close as he nuzzled my neck.
We’d fucked a few minutes when he asked if I’d get on top. He lay back and I rode his cock while he fondled my breasts. We both were savoring the sensations. I love this position, too.
I’d ridden him nearly half an hour. I could have ridden him much longer, but he asked if he could take me from behind. I lay face down on my bed and reached behind me to spread my cheeks. He lay on me as he entered.
“You can fuck me harder, if you want’” I encouraged him. “I won’t break!”
Soon, he was grunting as he thrust hard and fast into my ass. I was getting a little sore, but I’d discovered I liked being sore. If I wasn’t sore, then I had not been fucked well enough!
“Ooohhhh, baby, you feel sooooo gooood inside me!” I purred.
Gerald started fucking me harder, grinding his body against mine. I felt him stiffen just before he filled my ass with his load. He’d fucked me pretty nicely. I felt great!
I sucked him clean and he showered. He kissed me goodnight and smiled broadly, telling me what a great time he’d had. I told him I’d really enjoyed the evening.
I lay back, playing with my cock, reliving the evening. I’d just creamed all over my stomach and was about to shower when I heard a knock at the door. I slipped on a robe and left it open as I opened the door.
Gerald was back! I saw lust in his eyes, and embarrassment in his face as he looked upon me.
“I nearly forgot!” he said, as he handed me an envelope. He kissed me, then quickly left.
The envelope held a stack of twenties! Maybe Jo was right. I was getting fucked regularly and getting paid to do it!
Over the next few months, I saw several gentlemen. Some, more than once. One even took me away for the weekend! I was enjoying myself immensely.
I never asked for anything, but was grateful when someone left a gift. Not everyone left a gift, most didn’t. If a guy (or woman) bought me dinner, or even a couple of drinks, I would spread my legs. All I really wanted was good sex!
I was going to Sandie’s a couple of times a week. Most nights, I’d have one drink and check out the other girls. I went out to dinner with a few and danced with others at the club. One of the regulars, a cute, but heavy girl name Cynthia asked me to her place one evening. She wasn’t exactly my type, but I thought “what the hell…….”
Cynthia was very shy and quiet. She was probably in her forties, raven hair going gray. She had a cute face and sparkling dark eyes. She was maybe 5-2, but was fairly heavy. A BBW.
We drank some wine and made out on her sofa. I expected to suck her sometime during the evening. Most the girls I dated wanted just that.
“Would you mind if I fucked you?” she quietly asked. Nobody had fucked me recently and I was ready.
She wanted to undress me. I was wearing a very short dress that barely covered my bottom. It plunged to just beneath my navel in front and to the top of my ass in back. I was braless and wearing very tiny bikini panties.
Cynthia kissed slowly from my neck down. She moved my dress over enough to suck a nipple and fondle my breast.
“Very nice,” she commented, before resuming her downward explorations. She lavished several kisses on my stomach and licked and sucked my navel, she then worked her way up to the other breast. She nipped harder, causing me to yelp.
“Sorry,” she apologized.
I pulled her head in close and said,” suck and nibble and bite all you want! Just not so hard!”
She sucked and nibbled both breasts until they were quite tender. She turned me around and slid my dress off my shoulders. It fell to my hips.
Cynthia explored by back and sides with her mouth. When she reached my ass, she knelt behind me and pulled my dress over my hips letting it fall to the floor. She kissed and licked my bottom for many minutes.
I got on all fours, she behind me. She pushed between my cheeks and started tonguing my ass. Her tongue flicked across my tight pucker. It darted in my asshole as she worked her spit into me.
‘You’re so delicious, I could eat you all night!” she declared.
She laughed when I said, “Be my guest!”
But all good things come to an end and it was time for her to fuck me. Cynthia raised her skirt, presenting me with a nice seven inch cock. She positioned it against my pucker and pushed in. I could almost hear a pop as the head slid in suddenly.
“Oh, Baby!” she declared. “You’re sooo tight! You feel good!”
She pounded my ass for quite a long time. I was getting sore. I’m not fucked well unless I’m sore. My small cock was hard and I felt her balls slapping against my balls. I felt her stiffen as she emptied into me.
Cynthia pulled out and rapidly buried her tongue back into my ass, lapping up all her cream. When she finished, she had me stand and took my cock into her mouth. I came quickly and filled her mouth with my cream.
After I dressed, she fumbled with her purse and handed me some cash.
“I know you take gifts from some of the men,” She looked down and said, “I didn’t think you’d fuck someone as fat as I am.”
I could see tears forming in the corner of her eyes.
“I never ask for anything from my dates,” I replied. “I had a good time tonight! That’s all I’m looking for!”
I could see the gratitude in her eyes.
“Next time, you could take me to dinner, if you like” I smiled.
“Next time?” she asked, hopefully.
“Of course!” I exclaimed. “Maybe next time you’ll get naked and take me to bed!”
We dated a few more times. Each time in bed was better. She was a damned good fuck!
I noticed William, an earlier date, eyeing Cynthia. I introduced them and left them to have a drink. They left together and I’ve often seen them together since.
I was having fun, but it still wasn’t what I was looking for. Unfortunately, I didn’t know for what, or whom, I was searching.