Dreamspinner Press Year Five Greatest Hits

by Tinnean

  I couldn’t help but think that my days of having the best of both worlds were numbered. Sooner or later, I was going to have to make a decision.

  WITH BOTH my and Will’s best efforts, we managed to carry on as if nothing more than just nice, simple Master/sub fucking had ever happened between us. To be honest, it didn’t take a huge amount of effort on my part. More than anything else, I wanted my life to go back to something simple where I knew where I stood with both my Master and my girlfriend.

  When my phone buzzed and his name appeared with a message, I couldn’t decide on whether I was relieved or really not in the mood for him.

  Will: The house will be empty tonight. Can you come over at about 7?

  At a guess, we were going to be fulfilling that mutual desire we’d expressed for some more scenes, in character, rather than a normal session. That was good, though. The chance to get out of my own head, my own skin, for a few hours was appealing. Although where Will was concerned, I would probably not be the best actor.

  It was only just after 5:30 p.m., so I had time to go through my workout then shower routine before heading over to Will’s. I used the car journey as sort of a meditative thing, letting go of all of the stresses in my life so I could be what he needed me to be.

  He met me at the door wearing a high school football jersey and shorts. He looked so much younger, so much more innocent than how I was used to seeing him. He smiled warmly as he tugged me inside, then his lips were on mine before I had really gotten my bearings. He kissed me hungrily, his hands clawing at my long sleeved T-shirt, and I pressed him up against the wall.

  “My room,” he gasped, taking my hand and pulling me up the stairs to his bedroom.

  Only it had changed, just enough for me to recognize the scene. He had posters tacked to his walls, vaguely homoerotic images of WWF wrestlers and mid-90s boy bands, shirtless and in low-slung Levi’s. I had no idea where he’d gotten them from, but high school biology and chemistry books sat open on a desk that hadn’t been there the last time I was here.

  “What about your parents?” I asked, falling quickly into character.

  “They’re out all night,” he said, leaving the door open. “We won’t be interrupted at all.”

  “Oh god. I’ve wanted to do this for so long.”

  “Me too,” Will said, leading me to the bed. “I was hard for hours today. I thought everyone would notice when you walked past in the locker rooms after gym.”

  “You were all wet too,” I nudged him back until he was sitting on the edge of the bed, then attacked his neck with my tongue and teeth. “I wanted to lick the water right off your skin.”

  He groaned, the sound rumbling in his chest.

  “When you bent over in front of me in Trig, I thought I would come in my pants.”

  “Did you want my ass, gorgeous?”

  “Jesus. Yeah. I want all of you.”

  Our lips met then, a hungry, sloppy kiss that really did remind me of making out as a teenager. Will grabbed hold of me around the waist and pulled me on top of him as he laid back on the bed, cupping my ass with one hand and kneading it gently.

  “Fuck,” I groaned, grinding my dick against the vague area of his crotch.

  “I didn’t think we’d ever get to be alone,” Will said. He grasped both my ass cheeks in his hands and pulled me roughly against himself.

  “Kissing you once a day and jerking off three times a day, thinking about kissing you, isn’t enough,” I agreed.

  Will chuckled and helped me tug my shirt off over my head. Then he moaned in approval at the sight of my chest.

  “You’re so fucking hot,” he said, lust glazing his eyes. “You’re a man, already, you know? None of those skinny fuckers at school turn me on like you do.”

  He ran his hand through the light hair on my chest, down to my happy trail, then back up my sides.

  “Will you fuck me?” I asked him shyly.

  He kissed me softly on the mouth. “No, baby. I’ll hurt you.”

  “No, you won’t,” I protested quickly.

  “Can I suck you instead?” he asked.

  It took me all of about three seconds to process that request. “Yeah,” I answered.

  “I’ve never sucked a guy’s cock before,” he whispered. I had to bite the inside of my cheek to hold back my laughter. Will was a fucking pro at sucking cock.

  “That’s okay,” I said, gently running my fingers through his hair. “You don’t have to.”

  “I want to,” he said. “I want you to be my first.”

  “You’re so cute,” I giggled. “And you have too many clothes on.”

  “Help me out of them then.”

  We managed to extract him from his jersey, tugging it off over his head, and my hands went to thumb open his shorts. “Are you sure?” I asked him, hesitating and gently stroking his cock through his shorts.

  “Yeah,” he said, kissing me again. “I’m really sure.”

  “Okay,” I agreed.

  We shucked off the last of our clothes, then lay side by side, completely naked, drinking in the sight of each other. It was easy to pretend that this was the first time I’d ever seen him like this—every time he amazed me.

  “Wow,” I whispered and trailed a finger down his chest.

  Will shuddered and closed his eyes. He could be so beautifully vulnerable sometimes. I leaned in and kissed him.

  He pressed his hand to the middle of my back, holding me close as his other hand pillowed under his cheek. It was sweet and innocent, what we were pretending, making me nostalgic for those days when things were so much easier. What would my life have been had I met Will in high school?

  I don’t think either of us anticipated lying like that, side by side, holding each other close and looking into each other’s eyes. But we did, for long minutes, not talking or touching, just drinking each other in.

  Will’s eyes flickered closed, then he tentatively leaned in and captured my lips between his. I took a deep breath and kissed him back and rubbed his back reassuringly.

  “Okay. I’m ready for this,” he said softly.

  I didn’t say anything, but kept my fingers loosely wound around locks of his hair as he shifted down the bed until he was face to face, so to speak, with my dick. He frowned, then softly, nervously, his fist closed around my shaft and his tongue tentatively licked the head.

  “Holy shit,” I muttered, forcing myself not to just grab his face and push my dick into it.

  “Jesse, you taste so good,” Will said. He met my eyes and stuck his tongue out again, lapping at the slit and taking the first inch into his mouth. I simply laid back and enjoyed it.

  If I was actually playing at the teenage dream fantasy, I probably would have blown my load within seconds, his mouth was that talented. As it was, I was used to holding back my orgasm, and I put all of those skills in place as he tentatively took more and more of my cock down his throat, eventually gagging on it.

  “Hey, it’s okay,” I said, pulling him back up to me. “Don’t hurt yourself.”

  “Sorry,” he mumbled. I kissed the end of his nose. He was so damn adorable.

  “Do you have any lube?” I asked him, and Will visibly blanched. He was a good actor. “No, not to fuck with,” I laughed. “I want to try something.”

  “Uh, sure,” he said and reached over me to his nightstand, revealing a drawer full of gay porn magazines.

  “Can I see those?” I asked.

  “Shut up,” he muttered.

  I laughed. “Masturbation is not a crime, Will.”

  “Oh, for fuck’s sake. You sound like my father. Here’s your damn lube.”

  I took it from him and leaned in for another kiss. While he was distracted by my lips, I cracked open the bottle and poured a generous amount into the palm of my hand, letting it warm before I carefully took hold of his dick.

  He moaned appreciatively as I stroked him, making sure to use a different angle than he would have been used to when touching him
self. I’d learned a lot about how best to stroke a cock since I’d been with Will. After pouring more lube onto him, I scooted closer on the bed and ground my hips up into his crotch.

  Lucky for me, Will got the idea pretty quickly and thrust his hips back toward me. He gasped as the sensitive ridge of my cock caught against his, and we both groaned in pleasure as his lips worked my jaw, right along to kiss my lips again.

  It was too ingrained in his nature to be passive for long, so I wasn’t surprised when Will nudged me onto my back to continue our… wet hump, for lack of a better word. The lube was slicking both our stomachs so we could slide together, just enough friction to get off, while the sensation of another cock massaging mine was better than I could have ever imagined.

  “I didn’t plan for this,” Will gasped in my ear. “I just thought, you know, we could make out and jerk each other off.”

  “Do you want to stop?”

  “No,” he said quickly. “No, this is awesome.”

  We built a rhythm of thrusting and sliding and grinding against each other while I took the opportunity to grab his ass in both hands to guide his action. It was rare that I got to touch him like this, and I was going to make the most of it. All the while, our lips and tongues tangled together in one of the sexiest, sloppiest make-out sessions of my life.

  “Gonna come,” I gasped in his ear, and Will nodded in agreement, his face pressed into the curve of my neck.

  “Me too,” he moaned.

  I pushed up against him and his cock pressed firmly into mine, the extra friction of his smooth shaft sending me over the edge. I came all over Will Anderson’s cock—fuck, that was hot. He must have felt the extra wet heat because he bit down on my bottom lip as he released, too, and from my super-close vantage point, I could see the crinkles as his eyes screwed up in pleasure.

  We were breathing hard as I wrapped my arms around him, bringing him close to my chest, and he snuggled into my neck.

  “I’m covered in jizz,” he said after a few minutes, and my heart rate had returned almost to normal.

  I snorted with laughter and he started to giggle too.

  “That’s disgusting,” I said.

  “I know. We need to move before it starts to congeal and glue us together by our pubes.”

  I laughed even harder as we rolled toward the edge of the bed, then carefully peeled apart.

  “Gross,” I giggled and Will pushed my shoulder.

  “I am not gross,” he said, mock-offended.

  We argued good-naturedly for a few moments about who would get to shower first, then I just got in with him—partly to annoy him, even though I had a sneaking suspicion that it was what he wanted all along. It took a fair amount of scrubbing to remove two loads of come and lube from my stomach and happy trail, and for some reason both of us found this hilarious. It really was like being a teenager again.

  “I have to be up early for work in the morning,” I said as I got dressed again. “I’m sorry I can’t hang out.”

  “No, that’s okay,” he said, pulling on a pair of loose black pants and a white tank. I nearly drooled at the sight of him—and he knew it. “The party is on Saturday night. You don’t have to come, but you said to let you know when it was, so….” Will ran his fingers through his wet hair nervously.

  “I’ll be there if I can,” I promised. “I should get going before your parents get home.” I winked.

  “Yeah,” he laughed. “It was a good scene, Jesse.”

  “Definitely,” I agreed. “Good night.”

  “Night, Jesse.”

  THE PLAY party rolled around quicker than I could make a decision about whether or not I wanted to be involved, so by the time I left to head over there, I figured I’d just watch this time. It was sort of a contradiction, not wanting to play at a play party, and I was aware of that, but we weren’t at a place in our relationship where I was comfortable with the idea of letting other people inside the bubble that we had created for ourselves. So I turned up on his doorstep with a couple of bottles of beer—my own insurance policy to say that I wouldn’t get involved. One of Will’s biggest rules was not to mix domination and alcohol.

  “Hey,” he greeted me as I came through the kitchen door. It was just more familiar to me to come in through the back door. So to speak.

  “Hi,” I said and let him pull me into a one-armed man hug. “It’s good to see you.”

  “I’m glad you came,” he said, looking genuinely happy. “Go on through. Laura’s here, she was asking about you. I’ll be around later. I need to mingle.”

  Laura was sitting in Will’s lone armchair, the one big enough for us both to snuggle in. It was clear that she wasn’t in full Domme mode from the way she was dressed, but her tight black jeans and blood-red corset certainly made her fit in better than I did. Suddenly, I felt underdressed in loose blue jeans and my long-sleeve gray shirt.

  “Mistress,” I said, somewhat cheekily as I approached her with a big smile.

  “You little shit,” she laughed. “Come here and give me a hug. Where the hell have you been hiding? I haven’t seen you in months!”

  “I haven’t been hiding,” I said honestly. “I just thought you’d probably have your hands full at the moment.”

  “I do,” she nodded solemnly. “This is the first time I’ve been out since I had the girls.”

  “How old are they now?” I asked.

  “Ten months. Steven is looking after them both for the evening.”

  Steven was the husband who had been so welcoming to me when I was his wife’s submissive. He worked as a physiotherapist, and we’d always been friendly, although I had always been a little intimidated by him. In the end, Laura had chosen him over me, as I knew she’d always have to do sooner or later.

  I automatically sat on the floor next to her chair. Some habits die hard. Another sub approached us, a boy I wasn’t familiar with, and he dropped his head meekly as he stood before Laura.

  “Can I get you a drink, Mistress?”

  “Diet soda. Lots of ice,” she said simply, barely acknowledging the boy. She knew her act well. “I’m still nursing.” Laura shrugged apologetically at my beer.

  “That’s okay. I’m not sure many people are drinking tonight anyway.”

  “Will’s parties are by invitation only,” Laura explained. “There are enough voyeurs and exhibitionists around that alcohol isn’t banned, per se, but if someone is drinking, it’s sort of a sign that they won’t be playing. I doubt if Will will drink at all, and he’ll have another DM here as well, even though he’s the one in charge.”

  “What’s a DM?”

  “Oh, sweetie, I wish I could have taken you out to play,” Laura sighed, her hand smoothing my hair back from my face. “I forget how naïve you are. The DM is the dungeon master. Or mistress. They’re the unofficial bouncer for the evening; they make sure everyone behaves themselves. I’m guessing you won’t play tonight? I’m surprised to see you here at all.”

  “I won’t play, no,” I said, toying with the paper label on my bottle. “Master had a session with Shannon a few weeks ago that he let me watch, and she mentioned about tonight. I think I wanted to prove to him that I can support him in things like this, even if I won’t be public about our relationship.”

  “Not every D/s couple plays in public, Jesse.”

  “I know that,” I said defensively.

  “Good. I’m glad you know your own limits well enough to know that this is something you don’t want to be pushed on. I’m proud of you.”

  “Thank you.” Laura always gave me plenty to think about.

  The boy returned with Laura’s drink, and she smiled in approval as he walked away from her. I laughed at her obviousness as Will joined us.

  “Shit, guys, it’s been a long time since I’ve had someone on their knees for me,” she said as she took a long pull of her soda.

  “You can borrow my boy if you want,” Will said. I wasn’t sure if he was entirely joking.

&nbs
p; “I’m not sure Steven would appreciate that,” I told him.

  “Steven doesn’t mind,” Laura said. “As long as it’s not him who I’m asking to be whipped and restrained, he’s happy.”

  “I still can’t believe you ended up with such a vanilla guy,” Will said warmly, sitting on the arm of the chair.

  “We fit,” Laura said simply. “He’s had to make a lot of compromises to be with me, too, you know. He accepts who I am… I wasn’t joking when I said that he is okay for me to be involved in the scene as long as I don’t ask him to join me.”

  “Has he ever subbed for you?” I asked.

  “No,” she laughed. “Steven really is the most nonkinky man you’ll ever find.”

  We talked for a while longer before Will excused both of us to get new drinks. Once we were in the relative privacy of the kitchen, he got much closer to me.

  “There’s a possibility of me doing a demo tonight,” Will said with his hand on my lower back, steadying me. “How do you feel about that?”

  I winced. “I don’t know.”

  “Okay. It doesn’t matter if I don’t. Laura will happily take over for me, I already checked with her.”

  “Oh.”

  “Jesse,” he leaned into my personal space. I welcomed the invasion. “I will spank a reaction out of you if I have to.”

  “Shit,” I murmured as my body responded to his words. “Who would you be doing it with? What’s the demo?”

  “That’s better,” he chuckled. “It would be with Cooper. A rope bondage workshop.”

  “Who’s Cooper?”

  “The boy who got a drink for Laura earlier.”

  I was hyperaware that his hand had crept under the hem of my T-shirt to stroke the hot skin of my lower back. It made it hard for me to think, but eventually the mental image of a lean, toned blond boy came back to me. My Master wanted to tie this guy up? No freaking way.

  “I don’t think I’m comfortable with that.”