Chapter 6

Author’s Note: This story is a collaboration with my friend and editor, Harvey. We both contributed equally to its content and we hope you enjoy it.

I eased the key into the door of my new high-rise condo and stepped inside. I’d been making quite a bit of money working for Dana and I’d decided to buy a place of my own instead of renting one. I’d just come from the workout facility that was located on the ground level. It was such a nice change having easy access to a gym and pool instead of driving to 24-hour Fitness.

I grabbed a bottle of water from the fridge, sat on the couch, pulled out my laptop, and logged into Dana’s site. It had been a very interesting two months. Once I took my finals and my junior year ended, I had a long talk with Dana. The date requests had really been piling up, and because I had a lot of extra time because I didn’t have to attend classes and study she’d talked me into accepting three dates a week. I really didn’t mind, the extra work actually gave me something to do and kept me busy. However, there was a downside.

I’d gotten a lot of excellent reviews from the older men who used her service and that only begot more requests from similar clientele. Truth be told, some of these older gentlemen were customers that many of my coworkers balked at ... ummm ... servicing ... and I could see why. Those clients were in their 60’s and 70’s and they had ummm ... performance issues, and those dates often involved my index finger, their rectum, and doses of Viagra. They definitely were a lot more work, but I was always patient and took my time with them, and like always I ensured they all left satisfied. On the upside, those older men had a lot of disposable income and didn’t mind paying for longer dates, which put a lot more money in my pocket. But even though they left satisfied, satisfaction was something I rarely received from them. Dana even went so far as gently teasing me about being her geriatric specialist.

To add to my sexual frustration, I’d also been on a few non-sex social-type dates where the guys had wanted me as arm candy for a charity fundraiser, a family wedding, and a bar mitzvah. Another client had requested that I keep him company while he played bingo, and he’d had such a good time the next week he booked me to ride around in his golf cart with him while he was on the links. They were very easy dates because they only involved hanging out and talking. Unfortunately, I made a lot less money on those dates because sex wasn’t involved. I didn’t really mind it though, but they only seemed to add to my sexual neediness.

One bright spot in my less-than-totally happy existence was Lynn. Even though I had a hectic work schedule, I was able to see her about twice a month and we’d spend the day together. We’d go shopping, have lunch, work out together, and then spend the rest of the afternoon having mind-blowing sex at my condo. I found that it was really a nice change from being with men and it added a bit of spice and variety to my sex life. From time to time she’d also use her Feeldoe, but to be honest a real cock felt better to me than a silicone one. I wasn’t quite ready to think of myself as bisexual yet, but I loved the time we spent together and I always looked forward to seeing her.

My biweekly meetings with her also initially caused some friction between me and Dana. At first she hated the idea of me meeting with Lynn without charging her, but after I explained the situation and my need for friendship and having someone to talk to she reluctantly agreed and left me alone about it.

I felt so sexually deprived with regard to interactions with younger men I’d even kicked around the idea of trying to find a boyfriend. In the end, I decided against it. Having a normal relationship with someone now was all but impossible, because I reasoned any guy I might be interested in would be too jealous of the sex involved in my escorting.

While I sipped my water and scrolled through my prospective date requests, I came across an email from Dana and discovered that she’d sent me a somewhat unusual proposal. Edward had asked if I would have a two-hour dinner date with Ed, his son. No sex would be involved, just conversation, so he would pay the minimum hourly rate. She stated that Ed wanted to catch up and tell me what he’d been doing since our twenty-four-hour date.

My first reaction was to tell her no. Another short date that didn’t involve sex was really a waste of my time. However, the proposal was also intriguing. By the end of our time together I’d become fond of him in an older-sister type way, and I was curious about how his dates had been going since our little education. I emailed her back saying I’d meet Ed at the same steakhouse restaurant in Caesars where we’d had dinner at the start of our previous date. I told Dana to have Ed make a reservation for this Friday evening.

It was summer-time now, and I chose to dress a little sexier than I did for our first date. I put on a square-neck, spaghetti-strap mini-dress that showed off the top swells of my breasts with a thong and my strappy new black patent-leather Jimmy Choo sandals with four-inch stiletto heels. As I was putting the finishing touches on my makeup I had to admit that I really wanted Ed to still find me attractive. For some reason, I thought it would be a good idea to order an Uber to take me to take me to Caesars instead of driving my own car.

When I met Ed outside the restaurant it was completely different from the first time. He greeted me with a tight hug, that I was more than willing to return. Then he kissed me on the cheek, took a step back, and gave me a once-over.

“You look fantastic!” he exclaimed, “even more beautiful than the last time I saw you. I love that little dress and those shoes are really sexy,” he gushed.

I appreciated his compliments, and I was happy to return them since he was dressed much more appropriately this time. “Thank you so much, it’s great to see you too, and you look very handsome in that suit. The open-collar shirt is perfect for this searing heat.”

He put his arm gently around me as we walked arm in arm into the restaurant and we were again seated next to each other at one corner of a square table. Once we were settled I opened the conversation.

“So tell me, what’s been happening with you?”

“Do you remember me telling you about a girl I wanted to ask out but was afraid of being refused?”

“Yes, of course.”

“Well, I worked up the courage to ask her out and she accepted. So I took her to the high school baseball game and for an ice cream afterwards. When I brought her home, I gave her a friendly kiss, just a peck on the lips, and I think she was shocked that I hadn’t made a move on her. Maybe that’s why she agreed to a second date.”

“How old is she?” I asked.

“She’s 16, just like me.”

“I’m so glad she wanted to go out with you again, that’s wonderful news, I bet you felt great,” I said as the server came to take our drink orders. I asked for an iced tea, and when he requested a glass of pineapple juice I couldn’t help but think, It has to be a coincidence, or does he know how sweet that will make his cum taste?

“I felt amazing,” he replied. “I loved the expression on her face when I said good night and left. The following week we went out again, and I asked her what movie she’d like to see, and I think she was testing me because she kind of tentatively suggested a romantic comedy; she probably thought I’d immediately suggest an action or horror movie. But I surprised her again by immediately accepting her choice. I got the tickets and she led me way up high, away from anyone else in the theater.”

“What were you thinking when she did that?” Our drinks arrived, and we each took a sip before nodding our acceptance and ordering our dinners.

“I remembered what you’d told me about signals, and I figured she was sending one.”

“Good thinking, were you right?”

“I’m sure I was, as you’ll understand in a minute. About a third of the way into the movie, the couple on the screen kissed, and Andie, her name is Andrea but she goes by Andie, reached over and took my hand. I was very cool, doing nothing except lightly stroking the back of her hand and up her forearm. When she put her head against my shoulder, I figured that was another signal and I took my hand out of hers and put my arm around her shoulder.”

“Wow, it sounds like you were paying attention and were very attuned to her signals.” I couldn’t help but be proud of my star pupil.

“You taught me well, Elisa.”

“Go on,” I urged him. We’d skipped the appetizers when we ordered, and our entrées arrived very quickly, so we started eating and he continued his story between bites.

“Her next signal was very encouraging. She moved her hand, the one she’d been using to hold mine, and put it on my chest. So in response I very slowly slid my hand down from her shoulder and put it on her breast. She let out a little moan, and I felt her nipple hardening through her clothes.”

“Wow, that’s great.”

I felt desire beginning to awaken within me. I liked Ed, and he was a very handsome young man. We’d gotten off to a rocky start, but we had a really fun time together, and now he was relating how he’d put everything I’d taught him into practice.

“What happened next?”

As I gently prodded him to continue his story, my mind again drifted back to our 24-hour date and I remembered how good he’d become at pleasing me. With every word he said I was becoming more aroused.

“The couple in the movie were seriously making out, and Andie started fiddling with one of my shirt buttons. When she did that, I slid my hand down to the hem of her blouse and slipped it under to cup her through her bra. She kind of moaned softly and licked the side of my neck when I did that, so I squeezed her breast lightly and then I started rubbing my fingers over her nipple. She whispered that what I was doing felt really good, and I think I surprised her again when I told her she was beautiful and it made me happy for her to feel good.”

“You little devil,” I said with a smile. “You were definitely practicing seduction on her.” You’re practicing it on me too, even though you don’t know it. I could feel the moisture begin to build between my legs as I listened to him.

“I guess so. After the movie, we stopped on the way home and made out. She let me put my hands inside her blouse again, both hands this time. It was awkward doing that in the front seat, but I didn’t want to spoil the mood by suggesting we move to the back. We were both breathing hard and really getting into it when we realized we’d hit her curfew and it was time for me to take her home.”

I was trying, not completely successfully, to control my own breathing. “Did you take her out again?”

“Yes, I did, and I discovered that the third time’s the charm. When I picked her up, she was wearing a short little skirt, a tank top, and heels. Her nipples were poking into the top, so I knew she wasn’t wearing a bra. She said we should just go for a drive someplace quiet, so I headed out into the desert. Just as it was getting dark I found a dirt road and I drove down it far enough that we couldn’t be seen from the highway.”

He took another bite of his steak and then continued. “When I’d parked, she said we should get into the back seat, and as soon as we closed the doors she was all over me, kissing and touching me. She told me she really liked me, and that she loved that I was willing to go slow and take things at her pace, but it was time for me to stop being a gentleman and start being her lover. So I pulled her top off and started fondling her breasts and she just went crazy, kissing my face and my neck and moaning about how good it felt for me to touch her.”

I was having trouble keeping my body from squirming as I listened to him. I really wanted to feel his hands on my body the way he was talking about touching hers.

The more he passionately talked about moving closer to getting between Andie’s legs in the back seat of his Land Rover, the more wet and turned on I got. Finally I couldn’t hold out any longer; I reached down, took his hand, and put it on my leg right at the hem of my dress, about halfway between my knee and my pussy. He looked at me in astonishment, then he smiled and started sliding his hand up the inside of my thighs. I opened my legs to give him better access, and he slowly ran the tips of his fingers up and down the front of my soaked thong.

“Oh, God, he whispered. “I’m turning you on,” he said in utter amazement.

“We’re well past turning,” I whispered back. “I’m thoroughly turned on.”

“Well ... I ... ummm... “there’s more for me to tell you.” His fingers slid across my swollen clit and I almost came.

“Okay, please keep going,” I said, and the double meaning was clear; I wanted him to keep touching me while telling his story, and he knew it.

“Andie told me she wasn’t a virgin, she’d had sex one time with a guy and it wasn’t very good. She asked if I was a virgin and I said no, I’d been with one girl also, and I decided to be bold enough to say I would promise to make it very enjoyable for her.” He squeezed the top of my thigh and I whimpered. “She asked if the girl I’d been with was pretty, and I lied to her; she’s pretty, and you’re gorgeous, but I told Andie she’s prettier than you are.”

“That’s a good kind of lie.”

“Then she said she didn’t want to have sex in my car because she wanted our first time to be special, and in a bed. But she asked if I’d ever gone down on a girl, her friends had talked about it, and I said I had and it was great. She whispered that she would give me a blow job if I went down on her, and I just flipped up her skirt, pulled down her panties, and ... you know ... she told me later that she loved it.”

“Holy shit,” I said breathlessly. “You really did that?”

“Yeah, I did, and she came hard twice, and I thought she was going to crush my head when she clamped her legs around me. Then she pushed my head away and reached for my pants. She unzipped me, took out my cock, and she whispered that it was beautiful but it was really big. She didn’t hesitate, though, she just went down on it. She wasn’t very good, not near as good as you were, she couldn’t get more than half of it in her mouth, but she really tried hard, she got me off, and she swallowed most of it.”

While he spoke to me he was gently rubbing the lips of my vagina and the tips of his fingers brushed my clit. My secretions were now oozing down the inside of my thighs and it was very difficult to control my breathing. I looked around the crowded restaurant a couple of times, ensuring that I wasn’t drawing attention to our table.

“It sounds like she’s ready to go all the way with you,” I said between little sips of breath. I thought about his very sexy story and my mouth watered because I knew how good his cum would taste after he drank that pineapple juice.

He continued to gently rub my pussy as we spoke. “I think so, I’m taking her out next week and I hope we’ll be abIe to have sex.”

“I’m sure you’ll figure that out.”

I was very close to release and I took his hand in mine, moved it away from my vagina, and rested it on my thigh. I knew that any further stimulation would push me over the edge; I was never quiet when I came and I didn’t want to get kicked out of the restaurant, or worse.

My eyes seductively met his and a wicked thought entered my head. “Do you ever think of me, baby, of our night together?” I said demurely.

“Of course I think of you, Elisa. I think about you all the time, what kind of question is that?”

“I think about you too,” I purred. “I’m thinking about you right now.”

A little smile broke over his lips. “What are you thinking about?” he said in a slightly more demanding tone.

“I remember how well you learned everything I taught you, I remember how big your cock is, and I remember how good it felt inside me,” I cooed.

A smile broke over his lips, a big Cheshire-cat smile. “What do you think we should do about that?” he asked slyly.

He was acting a little cocky and that only turned me on more. I was impressed with his maturity. He was talking to me like a man way beyond his years, and he definitely wasn’t acting like the little boy that I’d first met.

“Do you have plans for the rest of the evening?” I asked seductively.

“No, I don’t, I was just going to go home after we finished dinner.”

I leaned in and whispered into his ear. “I want you to fuck me, just like you did before. Would you like that?”

“All the ways I fucked you before?” he asked in a deep, throaty tone.

“I’m yours, any way you want me.” To further make my point, I moved my hand down to his thigh and rubbed it over the very sizable erection in the front of his trousers.

He let out a little moan, but then suddenly a timid look broke over his face, which I quickly noticed. “What’s wrong, baby? I hope you want this just as much as I do.”

“I ... ummm ... it’s just that I...”

“It’s okay, honey, you can tell me,” I said soothingly.

“I don’t have any money, Elisa, my father only gave me enough to pay for dinner.” He paused for a moment to collect his thoughts. “He told me how much he paid for our night together, and I ... I ... you know ... there’s no way I can afford that.”

“This evening is on me, baby, okay?”

His eyes got wide. “Really, Elisa?”

“Yes, but I need you to promise me something.”

“Anything.”

“Do you remember me telling you about discretion? About never telling anyone what you do with a girl?”

“Yes, I remember.”

“If my boss ever found out about this, it would cost me my job, okay? You can’t tell your father, or anyone else, about this ... will you promise me that?”

He looked deep into my eyes. “I promise, Elisa, this evening will stay between us.”

“Thank you.” I’d made such a connection with him, I knew he was good to his word.

We exchanged knowing smiles. “So ... ummm ... what do we do now?”

“You pay for dinner, I’ll take care of everything else.”

“Okay.”

He signaled for the check, settled it with cash, and rose to help me up by pulling my chair back. He offered me his arm, and I managed to walk beside him in an outwardly calm way even though my body was sending desperate signals of sexual need into my brain. We walked out of the restaurant, and as we approached the long row of hotel desk clerks I stopped.

“I want you to wait here and I’ll get the room, okay?”

“Okay.”

I walked another twenty feet and one of the clerks waved her hand, so I walked up to her.

“May I help you, Ma’am?” the young girl asked. I found it funny that she called me ‘Ma’am’ considering we had to be about the same age.

“I need a room for the evening.”

“What kind of room are you looking for?” she asked politely. “We have several suites still available if you’re interested.”

“I just need a regular room with a king-size bed.”

She started typing away on her computer.

“Something close to the elevators, if you have it,” I added.

“How many nights will you be staying with us?”

“One.”

She typed more on the keyboard. “That will be $371.41.”

Jesus Christ. Being generous isn’t cheap, I thought sarcastically. Fucking in my condo was sounded a lot better but I knew there was no way I could wait that long. “No problem.” I reached into my clutch purse, pulled out my driver’s license and credit card, and handed them to her.

About a minute later she slid a keycard, my credit card, and my license back to me. “I’ve got you in room 304, right by the elevator.”

“Perfect, thank you,” I said hurriedly.

She gave me a little knowing smile. “Enjoy your stay, Ma’am.”

It took everything in my power not to sprint back to Ed, but I managed a briskly-paced walk. I grabbed his hand and tugged him towards the bank of elevators. “Let’s go, kid, we’re burning daylight.”

As soon as we got inside the room and I got the door closed I turned and slipped into his open arms. I lifted my face, and when he pressed his lips onto mine I instantly opened my mouth to accept his thrusting tongue. He put his hands on my breasts and moved them in slow circles; he obviously wasn’t waiting for any more signals from me. His palms rubbing across my nipples sent shockwaves through my body that reverberated between my legs, and I knew I was soaking wet with desire. Then he pulled back from our passionate embrace.

“Do you remember what we talked about on our date?” he asked.

In that hedonistic moment, all I wanted him to do was tear off my clothes, push me down onto the bed, and ravage me. However, this sounded somewhat serious, so I took a deep breath in an attempt to calm myself down and attempted to answer him in the calmest voice I could muster.

“Yes, baby, I remember, but is there something specific you want to ask me about?”

“You’re not like most girls, are you, Elisa?”

I had an idea of where he might be going with this, but I had to be certain. “What do you mean?”

“I mean ... you’re one of those girls who likes it when a man takes charge, aren’t you?”

He’s thinking of himself as a man now, I thought. I wonder how well he can actually read me. He’s only a teenager, but he’s a smart one. So I’m going to answer him honestly.

“Yes, I am.”

“Take off your dress, Elisa,” he ordered in a deep, throaty tone.

My eyes got wide. I’d never heard such a commanding, dominant tone on any of my previous dates and I definitely didn’t expect one to come from him, but it sent a thrilling, erotic chill through my body.

“Okay,” I said timidly.

I kept my eyes on his, reached behind me, and pulled down the zipper, then grabbed the hem of my dress, pulled it up and off my body, and let it fall to the floor at my feet. As I stood before him in my thong and heels, I waited for his next command. I have a teenager ordering me around, and I love it, I thought with a sense of wonder. How far will he go with this?

I didn’t have to wait long to find out. My nipples were already painfully erect and he started playing with them, teasing them and then pinching and twisting them roughly between his fingers. Intensely pleasurable sensations surged through my body straight to my vagina and I shivered as my need for him increased even more. Then he ran his fingers down my stomach to my thong and brushed the tips of them over my clit. My knees went weak and I wasn’t sure I’d be able to remain standing.

“You’re really ready, aren’t you,” he said in the same commanding voice, and it wasn’t a question.

I took another deep breath so I could answer him cogently. “You know from our time together that I get easily aroused, and I got worked up listening to you tell me about your dates. I don’t have a boyfriend, I haven’t been properly laid in a month, and touching myself isn’t nearly as good as the real thing. My body is on fire, and that’s because of you and nothing else.” I hesitated, then just blurted out, “What are you going to do about that?” I held my breath, waiting anxiously for his response.

“You told me it’s okay to talk dirty sometimes, so this is what we’re going to do. I want to last as long as I can when I fuck you, so you’re going to take off your thong and get me into your mouth. I’m going to come inside it, and you’re going to swallow it. Do you understand me, Elisa?”

I didn’t think, I just spoke. “Yes, Sir,” I said in a voice barely above a whisper.

“Get to it,” he growled.

It only took a second before I had my thong down my long legs. After stepping out of it, I dropped it on the floor next to my dress. Then I knelt, opened his pants, and pulled his cock out. He was already fully erect; I licked my lips and then took all of him into my mouth and down my throat in a single movement. I stuck out my tongue and licked his balls while I swallowed around his cock. He weaved his fingers through my long brown hair, and in an instant me giving him head morphed into him fucking my mouth and throat. I hadn’t thought there was a possibility of getting any hotter, but his new controlling, dominant nature took my passion to another level.

“You’re mouth feels so fuckin’ good,” he growled. “I’m almost there, get ready.”

He released my head and slid his cock out of my mouth to an inch or so away from my face. I looked up at him and opened my mouth as wide as I could. He began furiously stroking the length of his long shaft and he began to pant and moan; then his cock twitched and he shot a couple of long, heavy ropes into my mouth. As he became more unsteady on his feet his aim was a little off, and the next two shots painted my face and a little got into my hair. He was nearly spent, but the last remaining strands landed across my breast and nipple.

I gave him a couple of seconds to somewhat recover, and his eyes opened and he looked down into mine. I opened my mouth, showing him his load, and then swallowed. Then I took his shaft at the base and gave it a gentle pull, working out a large dollop of semen that collected on the slit of his cock. I took the large mushroom-shaped head into my mouth, gave it a hard suck, opened my mouth again so he could see what I’d collected, and swallowed again. Then I ran my fingers over my face, breast, and nipple and collected as much of his cum as I could before sucking them clean. Once again, I opened my mouth so he could see and I swallowed one last time.

“Thank you, I loved doing that for you,” I said demurely.

“God, you are so fuckin’ sexy,” he said with a little grin.

“Now you know one of my secrets,” I said with a smile. “I love being told what to do.”

“Tell me another secret.”

I had to decide what to say in response, and I decided to put him off. “I really, really need to feel your mouth on me,” I told him. “Give me what I need and then I’ll tell you.”

“Get on the bed on your back and spread ‘em,” was his next order, and I quickly complied.

He stripped off all his clothes and lay between my legs. There was no hesitation in his movement. He quickly got into the bed and dove between my open legs. There was no reluctance and no indecision as he sank his tongue deep inside me.

“Oh, God,” I moaned. “Yes, baby, just like that.”

I roughly squeezed my thighs together around his head while he licked the walls of my vagina. Almost involuntarily, I began to grind my pussy into his tongue and mouth. He must not have liked my more aggressive movements, because he quickly took control of me again by wrapping his strong arms around my thighs, which effectively immobilized me. Witnessing his subtle authority only made me more aroused.

“My clit, baby, my clit, please...” I moaned. “Get me there, please.”

He withdrew his tongue from me and began sucking on the hard little nub between my legs while his hands moved up to my breasts and he started roughly pawing on them. A few seconds later he squeezed both of my erect nipples, and the combination of pain and pleasure was intoxicating.

“Oh, fuck, more ... God, please ... more, I need more...”

He pressed his tongue hard on my clit and I exploded; I screamed so loudly I could probably be heard on the next floor. Just like I’d taught him, he withdrew his tongue from me and gave me a few seconds to recover. Once my breathing had returned to somewhat normal, I looked between my legs and our eyes met.

“I want more,” I said lustfully.

He gently bit my inner thigh and then lightly kissed the area that his teeth had just been. “Tell me another secret,” he said in a demanding tone.

“Please, baby,” I begged. “I need to feel your mouth again.”

“No, Elisa,” he said sternly. “You’ll get pleasure when I decide to give it to you, not before.”

My lust-addled brain refused to form a coherent thought. I loved the control he was forcing me to accept, but I wanted his mouth back on me. So I chose to reveal something small, something simple that would move him along.

“On our last date, I wanted you to take control of me like this, but I didn’t think you were ready for it,” I admittedly shyly. “You’ve surprised me, acting this way, showing me this side of your personality.”

He thought for a moment. “To be honest, I didn’t know if you’d like it, but I thought that it wouldn’t hurt to try. I knew if this wasn’t something you didn’t like, you’d tell me.”

My face split into a little grin. “I like it, I like seeing a different side of you.” I paused to collect my thoughts. “You’re maturing. You were just a boy when we met, but it’s like you’re–.”

“You turned me into a man, didn’t you?”

“Yes ... I ... ummm ... I guess I did.” I lovingly ran my hands through his hair. “You don’t regret any of it, do you?”

“No, you were perfect with me. You were patient, kind, and you made my first sexual experience something that I’ll never forget.”

I thought for a moment. “I’d never been anyone’s first,” I admitted circumspectly, “I was afraid of messing you up, or doing something wrong.”