Sugar Ch. 02

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Anal

1. All characters are 18+

2. No characters resemble real people

3. Enjoy the fiction

—-

CHAPTER 2

This next part of how I became a sugar daddy is my son’s fault.

Outside of the occasional text, I haven’t spoken to my son in over a year. He was upset that his mother divorced me, and upset that I let her go. He graduated from the university near my house, and moved to an apartment in the city, an hour away.

So he has no idea that I’m renting out his former bedroom to a 21-year-old co-ed named Amber. Furthermore, he doesn’t know that last night, she came into my room and gave me the greatest blowjob of my life.

In the morning, Amber and I kind of threw out some of the original rent contract. The basic rules of the house still applied – no drinking, no boys, etc. – but Amber’s payment of rent was much more, um, flexible. At least once a week, she’d get me off, more if she felt like it. Monetary payments would be less frequent as a result. And, most importantly, our new relationship was to be strictly confidential.

As I’ve said, I didn’t need the money. I was set, and I could support her too if needed. And I was still working, with no plans to retire yet. Maybe I’d have trouble supporting her if she was a flashy gold digger, requiring designer clothes and a luxury car. But Amber wasn’t like that. She had her own clothes, and she was incredibly happy with the used red Kia I’d bought for her.

—-

Halloween was coming up. I had bought a few bags of candy for the kids in the neighborhood. Amber was trying to avoid college parties and especially drinking, but she was being peer-pressured by her friends to come out and join them.

On one particular Thursday, about eight days before the big Halloween weekend, her friend Fallon was over. The two were using the study on the first floor, while I sat in my office upstairs. As usual, I wasn’t listening until the conversation turned to boys.

“You have to come. Please?”

“You know I’m trying to keep on the straight and narrow, Fallon.”

“I know you’ve been avoiding parties, yes. But this is Halloween, it’s an actual holiday.”

“Yes, I know what Halloween is.”

“Plus, I need you to be there, for support. I’ve been talking to this guy online, and we’re going to meet at the party. I need backup, for safety.”

Amber sighed. “For safety?”

“Yeah, you know, female solidarity. Help me make sure he’s not a sleaze.” Amber must not have been convinced, because she added, “Please?”

“Okay, fine. I’ll go, but I won’t be drinking.”

“Fine. Hey, maybe he’ll have a friend for you.”

“Yeah, maybe,” Amber responded. She had to, to keep our secret.

—-

Amber came to my bedroom that night, for what would be my third blowjob from her since we started this new arrangement. “I need some money.” She was dressed in her usual bedtime attire, a loose-fitting shirt and a pair of short shorts.

I was laying in bed, wearing essentially the same under my sheets. “For what?”

“I’m going to go to a Halloween party, and I need a costume.” She glided across the floor and sat on the bed with me.

“What kind of costume?”

She shrugged. “Don’t know yet. Something sexy?”

“Only if you wear it for me,” I said with a lascivious grin.

“Of course,” she said, smiling back. “Shall we?”

She reached to pull off her shirt, but I stopped her. “Can I?” I asked. She wasn’t expecting that, but she nodded, and raised her arms as I stripped her shirt from her body. “You have the greatest body I’ve ever seen in person,” I told her. “I can’t believe how lucky I am.”

She kissed me. “I’m lucky too. I was desperate. Any other guy would take advantage of me. But you’re different. With you, it’s so much more like a partnership. We’re both getting what we need.”

“We sure are,” I agreed. “Can I ask for one more thing?”

Amber eyed me. “If it’s intercourse, I don’t think I’m ready for that. Can we just stick to oral?”

“Oh, no, that’s not what I was going to ask,” I said quickly. “I, um, wanted to know if you’d take off your shorts too.”

“You want to see my ass?” Amber asked, and I nodded. “Sure.” She shimmied out of her shorts, showing off the thong she wore underneath. “Look familiar?”

I looked at the black material wedged between her perfect ass cheeks. “Is that the same one I found a few weeks ago?”

“Yup,” she said with a giggle. Then she helped me pull my shorts down, which released my dick to point at the ceiling. “I’ll do it this way tonight, so you can see me,” she told me, and basically kneeled to my side, taking my dick into her mouth sideways. From this angle, I could see more of her body: her breasts hanging down, her lovely waist and hips, and her slender legs.

Amber’s mouth was the main attraction, of course. She performed magic on my most sensitive part. The first time, I’d only lasted a few minutes. The second time was a bit longer. I was determined to last even longer tonight. If nothing else, it would prolong bahis siteleri the wonderful sensations she provided.

But seeing more of her body was a pleasant side show. I reached out my hand, and her back was just within reach. I placed my hand there, and gently rubbed her soft skin. She gave me a little “mmm” noise, and kept going, so I didn’t draw my hand away.

I wondered how much of her body she’d let me touch. Amber had told me she didn’t mind me asking, as she preferred that rather than me assuming. “Can I touch you more, sweetie?”

“Mm-hmm,” she said, without stopping.

“Come this way,” I said, and she shifted her body around, closer to my torso. I could still only use one hand, but now I could feel her whole back and, even better, her nice ass. It wasn’t too big, but was big enough to be more than a handful. I know because I moved my hand there and squeezed. This prompted another “mmm” as Amber sucked on me.

I was curious about touching underneath the black cotton of her thong, but I didn’t want to push things too far. Instead, I was content rubbing and gently squeezing both ass cheeks, as the vixen worked to make me cum. And when I did, as usual, she sucked it all up and swallowed it down. “You’re quite good at that,” I said, coming down from my climax.

She smiled pleasantly as she wiped her mouth. “I kind of liked you caressing my ass. Maybe next time, I’ll sit over you so you can do that more.”

“Yes please,” I said. “And if you like it so much, I’ll do it other times too.”

I meant it as a joke, but she grinned. “Yes please.” She leaned in and kissed me again. “Goodnight, Sam.”

“Goodnight sweetie.”

—-

That weekend, Amber went costume shopping with Fallon. Fallon thankfully didn’t ask where or how Amber got a hundred dollars. When Amber got home, she held up a bag for me to see. “I found one.”

“What did you get?” I asked, very curious what my cute tenant chose.

“You sit right there,” she told me, ” and I’ll model it for you.” I did as she commanded. Two minutes later, she called from the stairs, “Ready?”

“Ready!” I called back.

Amber came into the room wearing the sexiest cop outfit I’d ever seen. The top was black and shiny, and showed off her cleavage and just a strip of belly, enough to show her navel. The skirt was made of the same material, and as she turned for me, I saw it went just a few inches past her ass. But it was tight, not loose like some skirts. She wore a hat, also with the same material, and held a plastic baton. “I heard there was trouble in the neighborhood. Sir, you’re in violation of the code of conduct.”

“I’m innocent, officer, I swear.” I liked where this was going.

She poked at my chest with the baton. “I’m afraid I’m going to have to search you, sir. You might be concealing a deadly weapon.” Amber frisked my arms and chest before finding a hardness in my pants. “Is this a semi?” she asked with a grin.

I appreciated the joke. “If you give it a second, it’ll be fully cocked.”

She knelt at my feet and unzipped my pants. “Sir, I’m going to have to inspect this.” When she took out my penis, she remarked, “This weapon is cocked. It looks primed to go off.” Then she broke character. “You can’t get anything on my outfit.”

“Why don’t you take off your top, then, just in case,” I suggested. She tossed her hat and baton onto the couch. She then slowly unzipped her top and peeled it off, showing me her glorious rack once again. I swear her boobs defied gravity, but I supposed that was just a benefit of being 21.

Back into character, she announced, “Hands behind your back sir. Let me do my job.”

A few minutes later, after she was done sucking me dry, she stripped off her skirt and tossed it with the rest of her outfit. Then she climbed into my lap wearing just a pair of pink and red striped panties. “That was fun,” she said.

“It was very fun,” I agreed, wrapping my arms around her. “What made you pick the cop outfit?”

“Actually, I kinda like the baton. Seemed like a good way to keep drunk boys away. Plus, Fallon found a cute prisoner outfit, so we’re matching.”

“Ah,” I told her. “What about me?”

“You,” she said, kissing my neck gently, “are not drunk. And you’re not a boy, you’re a responsible man.”

“Would a responsible man squeeze the ass of a cute tenant?” I asked, doing so.

“He would if she liked it,” she cooed in my ear.

“Good. And for the record,” I said, “I wouldn’t mind you walking around the house like this a little more.”

She laughed. “What, topless? Keep the curtains closed and I’ll keep it in mind.”

“Really?”

“I feel comfortable with you,” she said, shrugging. “Speaking of which, you have a hot girl on your lap, topless. And you haven’t copped a feel once.”

I chuckled. “Are you asking me to touch your boobs?” Keeping my left hand on her ass, I cupped her left boob with my right. “Because you don’t have to tell me twice.” It was firm, but soft. Her nipple got hard in my hand as I groped her.

“Good,” canlı bahis siteleri she said. “That makes you a fast learner.”

“I’m not a complete virgin, you know. I do have a son. So I did have it figured out at least once, long ago.”

“I know,” Amber said. “It’s this arrangement we have.” She preferred the term arrangement to relationship, which made sense to me. “It’s pretty…”

“Unconventional,” I finished.

“Exactly. So let’s take it one step at a time and we’ll figure it all out together.”

—-

I saw Amber head off to her party. She wore her sexy cop outfit under a long coat, but she flashed it to me right before she left. “Have fun,” I said.

“You too,” she responded. “Don’t eat all the candy. Save some for the kids.”

“Haha.” I did eat a few candy bars in between the trick-or-treating kids, but when they stopped coming, I still had a few pieces left over.

I wondered if I should stay up and wait. Amber was an adult and could likely handle herself. But I wondered if she’d break her alcohol-free streak and partake with Fallon.

I did stay up, but I didn’t have to worry. A little after midnight, I heard stumbling feet come through the back door. When I went to check, it was a sober Amber and a sleepy-drunk Fallon. Amber was still in her cop outfit, minus the hat and baton. Fallon was wearing an orange prisoner outfit, which was also two-piece like Amber’s, with black numbers printed on one breast.

“You’re still up,” Amber said, surprised.

“Hi Mr. Sam,” said Fallon.

“Hi girls. Did you have a good time?” I asked, knowing the answer was probably yes.

“Yeah!” replied Fallon. “I’m just… a little tired now.”

“I see,” I said, then looked at Amber questioningly.

She quickly responded, “I didn’t have any, she drank them all. Let me put her in my room, and I’ll take the couch.”

“Take me to your room, officer!” Fallon muttered, and Amber led her upstairs. I followed, but went to my own room and closed the door.

Five minutes later, my door opened and Amber came in, dressed for bed. She noted my surprised look, and said, “You didn’t think I was actually sleeping on the couch, did you? When there’s a perfectly good half of a bed in here?”

“You’re in here, while she’s right across the hall?”

“She’s out. Like all-night out,” she replied, and crawled into my bed. “That said, maybe we shouldn’t do anything tonight, just in case.”

I nodded. “Okay. So, just sleeping?”

“Just sleeping. Cuddling is optional.” She held up her phone that she’d brought with her. “I set an alarm for 6 AM. That way she won’t catch us.”

“Good plan.” I laid down in the bed, and she curled up next to me, her back to me. I took the invitation and spooned up behind her. “Goodnight, sweetie,” I whispered into her ear.

“Goodnight, Sam,” she whispered back.

—-

When Fallon finally woke up around 8:00, she thankfully didn’t puke. But she was very thirsty, and hungry. She came downstairs wearing some of Amber’s clothes, rather than the Halloween costume from last night, and showed no sign of knowing that Amber had only napped on the couch for the last 2 hours.

I made the girls some breakfast, and then Amber took Fallon back to her dorm. The instant she returned, she thanked me. “For what?”

“Part of me can’t believe what a gentleman you are sometimes. I slept the whole night with you, and you didn’t once try to fuck me.”

I cocked my head to the side. “You haven’t met many good men.”

She straddled me as I sat in my recliner. “No, I haven’t.” She kissed me, and told me, “Thanks for being the first.”

She did tell me about her night. Guys did offer her drinks, and she turned them all down, drinking pop all night instead. Fallon met up with her guy that she’d talked to online, and they had clicked. “He’s a pretty nice guy,” Amber told me. “A little smarmy, but I guess it was Halloween and he was drinking too.”

“Maybe everyone seems smarmy when you’re the only one not drinking.”

“Fair point,” Amber conceded, “but he was wearing a white doctor’s coat that said ‘Dr. Seymour Butts,’ and he was trying to use his stethoscope on Fallon.”

“Ah, yeah that does sound a little cheesy. Was he a student?”

Amber shook her head. “I think he graduated. He just came back for the party, and to meet Fallon.”

I brought my arms around her, and cupped her ass with both hands. “Shame we couldn’t take advantage of the opportunity last night.”

“You want me in your bed?” she asked, and kissed me again.

“It felt good to have someone there again,” I told her. “Especially when that person was you.”

“Maybe we can make it a more regular occurrence,” she said, almost asking it like a question.

“I’d like that.”

She smiled. “So would I.”

—-

Thus, Amber spent most nights in my bed. She’d still stay in her room on nights she had to stay up late studying, or if she was on her period and didn’t feel like it. The first night was fully clothed, like canlı bahis the night of Halloween. After a few nights of that, it started being topless. Part of that was due to Amber’s great blowjobs. She always took off her shirt, so it didn’t get messy, and neither of us saw much reason for her to put it back on. And I took off my shirt too. Feeling her, skin on skin, kept me plenty warm at night.

We weren’t having intercourse. In fact, I hadn’t seen her fully nude yet. It was a boundary for her, so her panties had always stayed on. It took me a full week to realize how much it bugged me.

I told her so, one night as she climbed into my bed. “I don’t think I’m ready for that, Sam,” she said. “What’s wrong with what we’re doing?”

“I love what we’re doing,” I said. “Trust me on that. But sometimes… I feel like I’m having all the fun.”

Amber looked puzzled, then realized what I meant. “You mean… you want to bring me off too?”

I nodded. “Exactly.”

She thought about it. “I guess I don’t hate that you care about my needs. But I don’t want to, I’m just not ready to take my bottoms off.”

I had anticipated that. “You don’t have to,” I told her. I pulled out a small vibrating toy that I’d purchased earlier that day.

She looked at it and just said, “Oh. Oh!”

“Do you trust me?” I asked, and she just nodded. “Straddle me. Sit over my face,” I told her. She did, putting her magnificent ass in my face, covered this time by a purple thong. I felt her fish my cock from my shorts and start working the shaft with her hand.

I rubbed my hands on her bare bottom, and worked my way inwards, until I had a hand cupping her mound. I used a single finger to rub up and down her covered slit. “This is still okay, right?” I asked.

“Ohh, yes. It’s good,” she responded, then she took me into her mouth.

I could feel her warmth with my finger. She was quickly getting wet. But as much as I wanted to, I wasn’t going to go inside her thong. So I grabbed the vibrator and activated it. I placed it on the bare skin of her ass first, and she gasped a little around my dick at the new sensation.

“How long has it been?” I asked, knowing she wouldn’t respond. “How long since a man made you cum?” She whimpered, as I teased the vibrator around on her still-hidden taint. “Must be years. Am I right?”

“Mm-hmm,” Amber uttered, indicating my guess was accurate.

“Let’s change that tonight,” I said. I brought the toy around her lips, circling her heavenly hole through the fabric. “I want you to cum for me.”

The teasing, the dirty talk, the building arousal was only driving Amber to suck harder on my member. I was driving her crazy, and she was doing the same to me. I pushed the toy over her clit for just a second, and I was rewarded with a low moan.

“You liked that. Let’s do that again.” I passed over the same spot, and another, louder moan passed from her lips. The vibrations of her throat were affecting me as well. “Oh yeah, moan on my dick,” I told her, and passed the toy over again, and again, and she continued her noises each time.

“I’m going to cum. I want you to cum with me,” I told her. With that, I moved the toy back to her clit, and pressed it into her. The sensations must have driven her over the edge, as she squealed above me, and I felt her abdomen tense up. She took me deep into her mouth as a result, and that drove me to climax as well. For the first time, Amber couldn’t swallow it all down fast enough, and some of my semen dripped from her mouth onto my thigh.

“God damn,” she said, after swallowing most of it. “I haven’t cum like that in forever.” She licked up the drips that she missed, then tucked my dick back into my shorts.

“The toy did all the work,” I humbly said, putting it on the bedside table.

“The toy was nice,” she told me, climbing off me to face me again. “But what really did it was your words. You really got me going. At that point, I’d have been pissed if I didn’t cum after all that lead up.” She cuddled into my shoulder, and added, “And I’ll admit I really needed that. It makes it easier to sleep.”

I wrapped my arm around her, and kissed her on the forehead. “It does. Thank you for sharing that with me.” I used my free hand to pull the sheet over us both.

Amber closed her eyes, and in a few minutes she was asleep. I watched her breathe peacefully for a minute or two. How was it possible that this angel was here in my bed, sleeping on my shoulder? It was a blessing. If karma was real, I must have done something very, very right.

—-

The second week of November, I was sitting on my recliner with my sweetie on my lap. We were watching a movie, but she was doing an excellent job distracting me with tiny nibbles on my neck. And, as had become more usual than not, her shirt had been removed and tossed somewhere.

My phone rang, and it showed an unknown number. I didn’t want to answer, but with tax season around the corner, I thought it would be a good idea to check. “Hello?”

On the other end was a voice I hadn’t heard in a long time. “Hi Dad.”

“David.”

At the mention of my son’s name, Amber immediately stopped. She hopped off my lap and gave me some time alone.

“How are you, son?”

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