Chapter 39: Double Your Pleasure, Double Your Fun!

December 1978

Sunday morning was the usual swim and breakfast with Stephanie. I was sure my mom didn’t like the amount of time we spent together because I was a ‘bad influence’ on my little sister. I chuckled to myself, glad that Mom had no real idea of which one of us was the predator and which was the prey. I wondered if Mom would send Stephanie to a convent if she ever found out.

It dawned on me that Stephanie had no idea what I was doing today. I decided I’d surprise her with a detailed journal entry and see how she reacted. It would be amusing. She got up from the table, looked at me, checked to make sure Mom’s back was turned, and ran her tongue over her lips. She was bad. I kept my face completely stoic.

I planned to leave home about 10:15am which would get me to Erin’s house around 10:30am. It was only 33°F, according to the thermometer outside the kitchen window, so I would need my hat, gloves, and scarf. I liked Winter weather, so it didn’t really bother me to ride in the cold. Fortunately, it wasn’t snowing. My backup plan had been to ask Dad for a ride, but that might lead to uncomfortable questions.

It took a bit longer than I had planned, but at 10:35am I arrived at Erin’s house. I rang the bell, and she opened the door and told me to bring my bike into the garage. She went around to open it and I stashed it next to what probably was her bike. She closed the garage and invited me in through the garage door.

She showed me where to hang up my Winter gear and where to put my hiking shoes. I wore them because they were warmer than tennis shoes, but easier to pedal in than my Winter boots. I noticed both girls were wearing fuzzy sweaters and jeans. I couldn’t tell for sure, but most likely they had six or seven pieces of clothing, though I wasn’t particularly worried about that. It would all work out in the end.

Of course, I did need to confirm that they actually knew what they were getting into. I didn’t press them about it on Wednesday at the Lucia party because they had seemed fairly serious, but I was a bit concerned about the round-about way they discussed sex. Mary’s assessment was most likely right, that they were both virgins. They had implied they wanted to have sex, but it could also be that they just wanted the game with rewards.

Erin led me into the den, where I saw a chessboard on the coffee table, a few beanbag chairs and a roaring fire in the fireplace. Erin offered me coffee, and I accepted. I’d had it a few times before and I was developing a taste for it, but I still preferred to get my caffeine from Coke or Dr Pepper.

“Erin, both of you are aware of the rules, right? Of how this works?”

“Yes. You play chess and take off one piece of clothing for each piece you lose. And for each pawn, you have to kiss.”

“And you are both OK with that?”

“Yes!” they said in unison.

“And the prizes? Mary told you about that?”

“Yes. If you win, we have to suck you. If we win, you have to lick us,” Erin said as both girls blushed.

“And you’re OK with that, too?”

Both girls said ‘yes’, but I sensed a bit of hesitation from Cindy.

“Have you done any of this stuff before?”

“I’ve just done some kissing,” Erin said.

“I, uh, have kissed, and uh, let a guy touch my boobs over my sweater,” Cindy said somewhat haltingly.

“Given there’s two of you, what’s the plan? Do I get dressed in between?”

“Oh, we hadn’t thought about that!”

“Well, it might work out. There are only 7 pieces that can be captured and I have seven pieces of clothing because I wore an undershirt under my polo to help stay warm on the bike ride.”

“I have seven as well, because I have a t-shirt under the sweater,” Erin said.

Cindy chimed in with, “Me too.”

I wondered what my best strategy was. I figured win the first, lose the second would work out best. That way, if it was their intent to screw, I’d have some recovery time.

“Who’s going to play first?”

“It’s my house,” Erin declared. “So I play first!”

It seemed to me that Cindy was relieved by that. She might not actually go through with it, I thought. Not really a big deal, because Erin seemed much surer of herself.

We sat down at the board and she had me select a hand hiding a pawn. I got white, which made me happy. Much easier chance of winning and I could control the tempo of the game. I opened with 1 e4 and she responded with 1 ... Nf6, which I recognized immediately because I played it a lot when I was playing. I knew the line pretty well, so I figured I should be able to win.

The game developed as expected and her move 4 ... dxe5 captured my pawn. She gave a sly smile, and I knew right then I was going to have her later that day. She came around the board for a kiss and we had a soft kiss on the lips for a few seconds before she went back to her side of the board. Of course, my move was to capture her pawn with 5 Nxe5. I went to her side of the board and gave her another soft kiss. I didn’t need to escalate. That would happen soon enough!

The line developed as I expected and she played 13 ... Nxe5, capturing the first piece. As she took my knight off the board, I removed my belt. I wasn’t even going to show my feet just yet! I played 14 dxe5 to capture her knight, and she removed her sweater, revealing a tank-top. On my 15th move, I captured her knight, setting up an exchange. She removed a sock, as did I when she took the exchange.

On move 17, I took her bishop, and she had no chance to recapture a piece. She removed another sock. I was pretty much sure I would win, and I would keep some of my clothes on. I captured another pawn she couldn’t immediately reclaim, and she came around for a kiss. This time I parted my lips slightly, and she took the invitation to slip her tongue into my mouth. We kissed for a few seconds and she went back to her side.

We exchanged rooks, and I removed a sock and she removed her t-shirt. She was wearing a pink satin bra enclosing her small breasts. I smiled my approval. I made a move, and she was trapped. I had forced mate in two. She toppled her king.

“I guess you win,” she said shyly. “Should we go to my room so I can give you your prize?”

“Lead the way!”

I followed her upstairs and into a typical teenage girl’s room — pink comforter, Leif Garret poster, a Bee Gees poster, a couple of stuffed animals, and the obligatory desk and chair. She closed the door and patted the end of the bed, indicating I should sit.

“I haven’t done this before, so I’m not sure how good it will be. I mean, I know how I’m supposed to do it because of talking to Mary, but I’m not experienced.”

If she talked to Mary, then I’m sure she knew exactly what to do and exactly what to expect.

“I think you’ll do just fine!” I said, by way of encouragement.

“Mary said I should let you cum in my mouth.”

“That’s up to you.”

Of course Mary had. She was looking out for my best interests, like all my girls.

Erin knelt down in front of me and unbuttoned my jeans, then pulled down my zipper. She tugged at the waist and I lifted my butt and she pulled down both the jeans and my underwear. My mostly erect dick popped out.

“It looks so big!” she gasped.

Music to any guy’s ears, of course, but Melanie liked to remind me I was a little above average. And I had never whipped out a ruler like she had said. I really didn’t care, actually. None of the girls had ever complained.

She wrapped a small hand around me, stroked me a few times, causing me to become fully erect. She looked up at me and smiled, then opened her mouth and took the head of my dick in. She gently sucked while stroking me with her hand. She swirled her tongue around me and then slowly lowered her head to take more of my rigid dick into her warm mouth.

She went a bit too deep and gagged slightly and backed off. Knowing now how far she could go, she began slowly bobbing up and down, matching her motions with her hand that was stroking me. Mary had given her pretty good instructions because she felt really good.

Erin kept that up for another two minutes before doubling her speed. I know I didn’t have much longer, so I warned her.

“Erin, I’m going to cum soon!”

She stopped, looked up, and me, smirked and then returned to her bobbing, stroking, sucking and licking. Less than a minute later, I knew I was over the edge.

“Cumming, Erin!”

She immediately backed off, holding just the head in her mouth, swirling her tongue and stroking me with her hand. I groaned and fired into her mouth and she coughed slightly, but kept her mouth glued to my dick. I saw some dribble out the sides of her mouth, but I could feel her swallow my cum with each spurt, which only heightened my pleasure. When I finished, she bobbed a couple of times and then released me.

She got up and started to move to her desk. I guessed she was going for tissue, but I grabbed her, stood up and gave her the best French kiss I knew how, while pulling her into a tight embrace. She squirmed a bit, but I held her tight because I figured she was shocked, not upset. She returned the kiss with gusto once she felt me holding her that tight.

When I broke the kiss, she said, “Whoa! You kissed me with your stuff on my face and in my mouth!”

“Mary didn’t tell you that one, huh?”

“No! It was weird at first, but after you kissed me, I figured it must be OK.”

“Erin, you sucked me, let me cum in your mouth, and swallowed most of it. Why should I expect you to do that if I refused to kiss you afterwards?”

I let her go, and she wiped her face while I pulled up my pants.

“I hope we can play some more later!” she said with a wink.

“Anything you want!” I agreed.

I was glad I had brought four rubbers with me. That actually left me with just one, so I’d need to get some more. I figured I’d just go to the drugstore on Saturday.

She led me back downstairs to the den where Cindy was waiting.

Cindy had reset the board but was looking decidedly nervous. I had a flashback to Becky, but Cindy didn’t look quite as bad as Becky had.

“You did it?” Cindy asked.

“Yeah, I did. He came in my mouth and I swallowed most of it. Then he French kissed me with his stuff on my face and in my mouth!”

“No way!”

“He did. If he wins, he can show you.”

“I’m going to win!” Cindy said smugly.

I hoped she did, actually. I knew Erin would screw for sure. If Cindy could go through with letting me lick her, I was sure she would as well.

I drew white. I knew I couldn’t make an obvious blunder, but it should be easy enough to make minor mistakes and drop a piece, giving her an advantage that would lead to a win.

“Should I put on the rest of my clothes or play with a handicap?” I asked.

The girls giggled, “Handicap! That way you can get naked!” Erin exclaimed.

“But you already saw me, Erin!” I laughed.

“Cindy didn’t. And I want to see again!” she said with a huge grin.

“You could always have done it down here instead of your room, you know.”

“No, I was a little nervous about doing it right.”

“I wasn’t complaining!” I said. “It was a fantastic blowjob!”

“Thanks!”

I decided to open with my king’s pawn and Cindy played 1 ... c5, which was the Sicilian defense. On move 3, she captured a pawn and shyly came to my side of the table. She was looking down at her shoes and I put my hand under her chin, lifted her face and gave her a soft, short kiss on the lips.

I found it somewhat amusing that she had let a guy touch her breasts over her sweater, but was shy about a kiss. I wondered if Erin had somehow put her up to this, or her shyness was just natural. I still wondered if she would go through with the prizes, win or lose.

On move 12, she captured an offered bishop to start an exchange. I removed my shirt, and she pulled off a sock. On move 15, she took my proffered bishop, and I removed my t-shirt. On the next move, I captured her knight as part of the exchange and she removed a sock. A few moves later, we exchanged knights, causing me to lose my jeans and her to remove her sweater revealing a plain t-shirt.

On move 19, I captured one of her pawns en passant and she came for another kiss. This time she looked up instead of down. I still put my hand under her chin and kissed her gently with parted lips. I felt hers part and touched my tongue to hers and then broke the kiss.

She didn’t bother moving back to her side of the table, but captured my pawn. This time we embraced, and I gave her a deep French kiss, certain she could feel my erection pressing against her leg. I looked at the board and saw a weak move that wasn’t too obvious and made it. A move later, she exchanged queens and I could see she had a clear line to victory.

I stood up and dropped my underwear and kicked them off. Erin smiled and Cindy’s eyes grew wide. I knew I could exchange a few more pieces and pawns before she’d win, and so on my next move, I captured a pawn, leaving a chance for her to exchange rooks.

I went to her side and gave her a searing French kiss and pressed hard into her so she could feel my erection. When I broke the kiss, she exhaled strongly. I knew I was working her up. She took the rook exchange and removed her t-shirt to reveal a white lace bra covering her firm breasts.

I made another move, setting up an exchange of bishops which she took and removed her jeans to show matching lace panties. To me, that told me she had prepared for me to see them. They seemed a bit too sexy for just casual wear, but then again, Melanie almost always wore sexy underwear. Of course, Melanie was ready to screw at the drop of a hat, any hat, so that might explain it!

I set up an exchange of rooks, knowing that she’d be able to win in a few moves after that. She looked across the table and met my eyes, then reached behind her back and unhooked her bra. She crossed her arms and pushed the straps down, and slowly let it fall. Her cream-colored skin highlighted her red nipples and pink areolae. Her breasts were as close to perfect as I could imagine, short of her actually being Jennifer, who I thought had perfect breasts.

As predicted, two moves later, she won.

“Cindy, you can use my room if you want to collect the prize.”

Cindy slowly got up and walked towards the stairs. I followed her upstairs and into Erin’s room. I shut the door behind us and Cindy turned to me.

“What do I do?”

“Take off your panties and sit on the edge of the bed, then lie back.”

She hooked her fingers in her panties and pushed them down, revealing sparse blonde pubic hair and very full labia. She sat down on the edge of the bed and leaned back on her elbows, looking at me expectantly.

I knelt in front of her and nudged her legs apart, then lowered my head and gently touched her pussy with my tongue. Cindy twitched at the contact, but she also let out a long sigh. I gently pressed my tongue between her labia and licked softly from bottom to top, eliciting a soft moan. I repeated the lick and was rewarded with another soft moan.

I probed between her labia for her opening, and finding it, I pressed my tongue in softly. She flinched at contact with her hymen. My guess is that she would be like Anna — feel a pinch and then be fine. I began licking her more roughly, moving my tongue up and down and occasionally swirling my tongue into her opening, careful not to press too hard on her cherry.

She was clearly getting worked up, so I gently flicked her clit with my tongue, eliciting an “Oh!” from her. I did it again and was rewarded with a moan and a buck of her hips. I returned to licking her slit for a moment, then quickly flicked my tongue up to her button. She bucked harder, so I put my mouth over her clit and gently sucked and lashed her clit with my tongue. She bucked a few times, then groaned, arched her back and shuddered. She collapsed on the bed, panting.

I was tempted to take her right then and there, but I wasn’t sure that’s what she really wanted. I didn’t want her to give up her cherry in the heat of the moment. This was different from Kim, who I had known for years. I gave her a minute to recover, then took her hand.

“Thanks,” she whispered. “That felt SO good!”

I kissed her softly, she slipped her panties back on and we left the room to go back downstairs.

“Erin, that was SO good. Mary was right! It felt better than anything I’ve ever felt before!”

Erin offered more coffee or hot cocoa. I opted for the cocoa. She made cocoa for all three of us and we sat on the floor of the den and drank it. I was going to let this play out however the girls wanted. I knew for sure that Erin wanted more.

I saw the girls exchange a look. It was pretty clear they had discussed the possible outcome of the games and were trying to decide what to do next.

Erin said, “Cindy and I need to talk, just wait here, please.”

“Sure,” I agreed.

The girls went upstairs, and I took the opportunity to empty my bladder, as my erection had subsided. I sat back down on the floor and finished my cocoa. The girls returned after about five minutes. I just waited for them to tell me what they wanted to do.

“Can we do something without playing chess for it?”

“What did you have in mind?”

“We both want to try what the other person did with you. Is that OK?”

“I’m game!” I said, standing up.

Both girls got up as well. That was interesting! Erin led all of us up to her room. Erin quickly removed her bra, revealing very firm breasts with light brown areolae and nipples. She quickly shed her jeans and panties and I saw a very neatly trimmed patch of curly brown pubic hair.

Erin, clearly taking the lead, said, “Cindy, you go first? OK?”

Cindy nodded. I sat on the edge of the bed and reclined on my elbows to watch. She got down on her knees between my legs.