The Education of a Cuckold

by Alex Hathaway

  But before I could ask her out, circumstances intervened. Kristen decided to open her own massage business with a few of her colleagues. Her current boss was a bit of a tool, and I had been encouraging her to strike out on her own. Without thinking, I volunteered to be one of her first clients.

  “Really? That would be awesome! And we could work on your back.” I had hurt my back playing soccer, and she had already shown me some exercises I could do on my own to help stretch and loosen it. So it was arranged.

  I should have realized that paying Kristen as a massage client would change things between us. I liked that I had some money to spend on a girl, so maybe I got carried away thinking I could make an impression on her by investing in her endeavor. Yeah, I was limited to a teacher’s salary and couldn’t exactly take Kristen island hopping, but I was making way more money than I had in college, and I was thrifty. I could afford to spend on a girl.

  The first time we actually had a formal massage appointment, as opposed to her just showing me stretching exercises, Kristen’s office air conditioner was down. It was unseasonably hot that summer, and a massage without air condition wasn’t going to work. Kristen called me and asked if I would do the appointment at her place, where she also had a table.

  Two hours later, I was there. I was a little taken aback by her outfit. She was wearing a short white skirt and an expertly beat up pink t-shirt that clung to her breasts, which were anything but small. I felt a twitch, then relief, that I was wearing tight underwear, so I wouldn’t get a boner on the table.

  She showed me into the massage room, which was right next to her bedroom. Just looking into Kristen’s bedroom and imagining what she must get up to in there was pretty overwhelming.

  “I’ll leave you to get ready,” she said. She lit some incense and put Native American flute music on.

  I got up on the table, kicked off my shoes and shirt, and waited for her knock.

  When she came in, she looked surprised.

  “Um, you’re not quite ready yet.”

  “I’m not?”

  “Yeah, you see, the towel here … that’s to rest on your midsection … underneath that … well, you don’t wear anything.”

  “You don’t?” I said.

  “No. I thought you said you’d had a massage before,” she said in that über-confident way of hers—that alluring combination of warmth and teasing.

  “Yeah, I have. Shiatsu with Alexandria.”

  “Oh, okay … Well, this isn’t Shiatsu.” Kristen smiled. “For this kind of massage, you take all your clothes off. But don’t worry, I won’t look.”

  Kristen went out in the hall. I nervously got my clothes off and lay down on my stomach. I made a point of covering my mid-section with the towel. I wasn’t opposed to being naked around Kristen, but not when I was basically on her turf like this.

  She made no further mention of it and started to work her way up both my legs, starting with the toes and the feet. She spent quite a bit of time on the feet, which was good because it let me think about other things. But when she started kneading my thighs, I couldn’t help it. Those long, sure-gripped fingers … I was having trouble not getting excited.

  “Roll over for me, Jason,” Kristen said. Or commanded.

  I dreaded rolling over, but there was nothing I could do now. I twisted onto my side, and then my back, trying to will my erection down. But it was hard to do, watching her breasts peek out from that tight t-shirt and her strong legs outlined by her skirt, in all their yogafied magnificence. It was too much.

  Kristen seemed to quell a smile when I turned over, my dick making a tent out of the towel, but she didn’t reveal much. Instead, she returned to kneading my feet, working on my toes, tugging each one till it popped. That’s it, stay down near the toes, I thought. Or work on my neck.”

  No such luck. She started working her way up my right calf again; then she was past my knee, rubbing and pressing up to my upper thigh. Damn that felt good. I couldn’t remember ever being so hard. I was embarrassed about it, but I was well past the point of being able to do anything.

  “This isn’t going to work,” Kristen said. “You’re just too tense right now. Let’s deal with that. I think I know what your dating problem is, or at least part of it.”

  With that, she reached her hand under the towel and started stroking me. I had never felt this kind of sensation from someone else’s hand. She just drove me wild. My cock twitched and strained. Then without asking my permission, she tossed the towel onto the floor and took a close look.

  “Yeah, I thought so,” she sighed as she stroked.

  “What is it?” I asked, scared and excited about where this conversation was headed.

  “Jason, you have a little dick. I’m really sorry to say it, but it really is so true.”

  It had been a long time since someone had talked to me that way. What was scary was how much I had missed it. She stroked while she was talking, looking at me in a kind way, but also a forceful one. I thought maybe she would start laughing but she settled for a hint of a smile.

  “This would explain your shyness in asking girls like me out.”

  “But does size really matter?” I asked her as she worked her hand on my cock, inspecting it more closely now.

  “Oh yeah,” she said. “In more ways than you can imagine. Most girls don’t have the guts to be honest about it. I’m not one of those girls who keep quiet about what she needs, as I think you know by now.”

  “What … ways?” I asked, scared to hear the truth I had sensed for so long. And yet I wanted to know. No, I craved the truth. Not just intellectually, but sexually. I watched her arm flexing lightly as she casually stroked me. I was already close to cumming. I had to dial that back a notch.

  “Well, for starters, I wouldn’t be able to feel you inside me,” she said matter-of-factly. It was like she could sense that I wanted the truth. The problem was, I couldn’t tell if she respected me for asking for it, or if she felt sorry for me. Maybe both. “I fucked a cock as small as yours once. He tried real hard, but he couldn’t do anything for me. I had to put his mouth up on me instead. You’d slip out a lot, too,” she added. “I’d have to concentrate just to keep you inside. That’s not a problem with a nice big cock.” She stared at me to let the truth sink in, continuing to stroke me with her right hand.

  I couldn’t recall being harder in my entire life. I willed myself not to cum, but it was too late. Looking at how ruthlessly she had eliminated me as a sexual contender, and how directly, imagining her wailing and slamming on a big cock, losing control, getting fucked by someone who was not intimidated by her sexually like I was … It was all too much for me.

  “Oh my god,” I said as I squirted, feeling my body quiver with ejaculations.

  She lunged for the towel, but she hadn’t expected me to cum so fast either, so some of my cum landed on her pink shirt.

  “Yeah, not a big surprise there,” she said, almost talking to herself as she wiped the cum off her arm and shirt before wiping it off my belly. She laughed a little bit, but it didn’t really hurt my feelings. She wasn’t a mean person. From my experience, mean would have meant leading me on. Mean would have been cheating on me or breaking up with me for no reason. It was impossible to be mad at her for shooting straight. Not to mention making me cum and not ignoring me sexually like so many beautiful women had done.

  “Well, at least you’re relaxed now,” she said. It was true.

  That orgasm had really cleared my body out; I was floppy loose all over. She put a new towel back over my midsection and went to work kneading my shoulders and neck before finally flipping me over again and working on my sore back. The talking stopped. I actually dozed off for a while, feeling more relaxed now that the scene was over and my towel covered me up again.

  When the session was over, Kristen woke me, leaving the room so I could get dressed. As I zipped up, I felt sad. Here I had been thinking I might make love to her someday.

  Kristen had a g
lass of water ready for me in the living room. She patted the couch for me to sit and drink. It felt strange to cut her a check for what had just happened. Or maybe it was illegal.

  “Are you feeling … discouraged?” she asked.

  I wanted to deny it, but she asked me so directly, looking right into my eyes. There was really no way I could.

  “Yes,” I confessed.

  “Oh, don’t be,” she said. “First of all, not all girls care about … well, size. I guess most of us do,” she smiled to herself, perhaps a little too wickedly, “but you only need to find one.”

  “I’ve been looking,” I said.

  “Well, it may take some persistence,” Kristen said. Again I thought she might laugh but she just smiled a bit, as if thinking about some of her friends and what they would say if they knew my real size. “Hey, I have an idea, if you’re up for it. Why don’t you come back for a while, see me here every week? We can work on your back—it needs some more fine tuning—but I can also help you with your … confidence. We’ll do the appointments here … at my place.”

  “My confidence?” I asked her.

  “Yeah. You said you were feeling discouraged. I think I can help you through that.”

  What the heck did she mean by that? And where would this lead?

  Of course I immediately agreed. I was terrified but also drawn to her piercing grasp of my insecurities. I wanted to see where it would go. How could she make me more confident? That I would have to see to believe. But the fact was, I was in a sexual dry spell. I didn’t have other options at the moment, and that was the best cum I had experienced in months.

  The next time I came to see Kristen, a part of me was hoping she would be dressed professionally. Again I was disappointed. She seemed to have an endless collection of faded t-shirts that clung to her breasts just a bit too much. This time, she was wearing jeans that hugged her hips unfairly. God, how I wanted her!

  She led me into the massage room.

  “This time, no towel,” Kristen said. “Just get naked.” She stood with her arms crossed, waiting for me to strip.

  I looked at her, uncertain.

  “Look, I already saw you last week,” she said. “Part of your job here is to get comfortable being naked around me, not shy at all, okay?”

  I nodded. That’s when I realized I was excited. She was pretty much a guaranteed adventure for me, no matter what happened. I was excited as I took off my clothes. My erection popped right out and Kristen couldn’t help but crack up. I couldn’t tell if she was laughing at my size or just that I was already hard just being around her.

  When I lay down on the table, my erection was still mostly up. She laughed. “That’s okay. It’s nothing to be embarrassed about.” She came up to the table and started working a bit on my feet, as if she handled men with erections all the time.

  “So here’s the plan,” she said. “We’re going to do this kind of like the military.”

  “We’re going to break you down and build you back up. When we’re done, you’ll be ready to go out there and break hearts.”

  “Break me down? I feel broken enough already,” I said.

  “Yeah,” she said, “you’re discouraged, but you’re still thinking about your chances with girls the wrong way, and it’s not going to work.”

  “So what is going to work?”

  “Acceptance,” she said. “We’re going to start with acceptance.” By this time, she was working her way up my legs again. Her firm hands felt amazing. You could always sense that she was holding back on the amount of pressure she was exerting. But that she could inflict more at any point.

  “Acceptance of what?” I asked.

  “Small penis acceptance.”

  My cock twitched.

  “That’s the first step,” Kristen said. “You need to totally accept who you are. It may be hard at first”—she had a trace of a wicked smile again—“but eventually you’ll embrace your identity completely, with its advantages … and limitations.” As she spoke, she was staring at my cock. God, her honesty was refreshing. So firm, but yet not cruel.

  “And,” she added, “I’ll teach you how to use all of it … to get … what you want …”—she rubbed and squeezed my calf muscles as she talked, loosening me up as she went—“from girls!” she added finally, somewhat unnecessarily.

  That sounded pretty good, if it was possible. But I was more afraid of what might be coming next.

  “Okay.”

  “So would you agree that you are building up to a big orgasm?” Kristen asked.

  “Yes,” I had to agree, hoping, praying—anything—that she would touch me again.

  “Good,” she said.

  Then she reached into her pocket, got out a condom and opened it.

  “This is one of my boyfriend’s condoms,” she said. “Or, more accurately, this is the condom from a guy I recently fucked.” She opened it out to its full size. “As you can see, this condom is specifically made for large penises.” Kristen stretched it out as she talked. It seemed to be nine or ten inches long. “I can’t tell you how many times I have slid this extra large size condom on a big cock, usually in a hurry, with my pussy all tingly and itchy. Now I’m going to put this condom on you.”

  She slid the base of the condom on and quickly rolled it up my shaft. “Yeah, just what I thought,” she said.

  “What?”

  “You are very loose in here, can you feel it?” she asked me.

  “Yeah,” I said. She had to bunch her hand around the condom to get a grip on me inside.

  “But you’re really hard, aren’t you?” she teased me forcefully.

  “Yeah.”

  “That’s it,” she said, stroking me with her right hand through the condom. “Let’s get you even harder if we can!”

  I couldn’t imagine being any harder, but seeing her muscular arm flexing and her eyes teasing me, I felt like I was going to burst. But I wasn’t ready to cum yet. Or at least I didn’t want to be.

  “Okay, I don’t think you’re going to get any harder, so let’s see where we’re at.” With that, she placed her right hand at the base of my cock and held the condom in place. With her left hand, she pulled out the end of the condom, stretching it out into the air.

  “Take a look at that,” Kristen said. “There’s more empty space above your penis than there is you inside it. You’re swimming inside there! And look at the thickness.” She showed me, pulling easily at the base of the condom. “There’s no way you can realistically wear this condom. We’d have to attach it with a rubber band.” She actually laughed out loud at that, having felt my cock twitch and jerk involuntarily.

  “Let’s try something.” She pulled at the tip of the condom, which slipped off my cock with no resistance.

  “Wow,” Kristen said, “let’s just hope you are never with a girl who only has this size condom. Actually that’s a good lesson for you. You should always carry around a snugger condom. Okay, I think we’re getting close to the end of today’s lesson. I know this isn’t easy for you, so I want you to get some enjoyment out of this.”

  With that, she moved to the right side of the table and put my hand on her right breast, covered only by her thin shirt—no bra.

  “Do you like how that feels?” she asked.

  I was amazed by how firm and large her breasts felt to my touch; I had never felt a pair that large before. They dangled down naturally and she was clearly fine with that. I could see her nipples protruding sharply.

  “Here, let me help you with that,” she said, and she pulled off her shirt without hesitation. Suddenly her big full breasts were swaying, and she had my hand on top of them.

  “Does that feel good?” she asked.

  “Oh yeah,” I said. My cock was so hard it was painful, and she wasn’t even touching me at the moment.

  “Okay, so we’re going to play a game to test your endurance. Small guys like you are always shooting off too quickly. I think it’s because you don’t have much sex
ual experience. You need to learn how to last longer, to show some ability to get into a rhythm. I’m going to stroke you, but not too fast, and I want you to stroke my breasts as well and try to hold off from cumming as long as you can, okay?”

  “Okay,” I said, uncertain of my staying power.

  “Mmm …” she said. With her left hand, Kristen guided my hand to her breast and showed me how she liked it touched—not too roughly, but more firmly than I would have thought. She showed me how and when she liked her nipples pinched—again, harder than I thought, but not when they were fully aroused.

  With her right hand, she continued to stroke me with the condom on while instructing me. I was imminent.

  “You like holding those big tits.”

  “Oh yeah …”

  “You’re pretty lucky. It’s been a long time since I let a guy with a dick as tiny as yours see me naked. I let my lovers put their big cocks in between my tits all the time. The guy who donated his condom for us … I lick the head of his dick from between my tits. Maybe we should try that sometime.”

  The casual stroking continued.

  “You’d get lost in between these tits,” she said, “just like you’d get lost inside my pussy.” No laughing this time, just a firm look. “You do realize pussies like to be filled up, right?”

  “Yeah,” I said.

  “Yeah, we really do like to be stretched. You should see how I act around a guy who can really fuck me.”

  Her grip was getting firmer around the condom.