Chapter 2
When I got to the house, I went inside, poured a drink, and sat down to wait for Anne. I let her in when she arrived shortly before ten. She dropped a small duffel bag on the floor, wrapped her arms around my neck, and kissed me.
“It’s an exciting night for you tonight. What do you think about your mom getting married?” Anne said as we walked into the living room.
“I think it’s great, Anne. I want Mom to be happy. Would you like a drink?”
“Sure. I’ll have whatever you’re having.”
I poured Anne a whiskey and refilled my glass. When I got into the living room, Anne sat on the couch. I sat beside her, gave her the drink, and took a sip. She put her whiskey to her lips and swallowed about half of it.
Anne leaned close to kiss me after placing her glass on the coffee table. I put my drink down, wrapped my arms around her, and returned her kiss. Anne moaned into my mouth as I touched her chest and massaged her braless breasts. A moment later, she pulled her shirt over her head. We were in a frenzy as we stripped each other down to our underwear. She extracted my cock and started giving me a blowjob. Anne knelt on the couch, bobbing her head as I stroked her back. When I slipped my hand into her panties, she moaned.
I stroked Anne’s ass and ran my fingers between her cheeks. I froze when I got to her anus, feeling something was there. Anne removed her mouth, stood up, shucked her panties, turned her back to me, and spread her butt cheeks.
“It’s a butt plug. I have my period, so I put this in to open my anus. I want you to fuck my ass.” Anne smiled. “Thanks for shaving your nuts, Jeff. I love it.”
I gazed at the green jewel in her ass, then shrugged my shoulders. “I’ve never done it before, Anne.”
“I guess we get to share another first, don’t we?” Anne said.
“Let’s go up to my bedroom. Mom’s gone for a few days.”
Anne grabbed her bag and headed for the stairs as I followed her, watching the green jewel winking at me between her butt cheeks. When we got to my bedroom, she dropped her duffel bag, turned to me, and kissed me as we moved toward the bed.
Kneeling between my legs, Anne stroked my cock, smiled, and took me into her mouth. I ran my fingers through her hair as she noisily sucked my cock. Pulling her head up, Anne pressed my shaft against my stomach and sucked on my hairless balls.
I rubbed my hand down her back to her ass, gripped the end of the butt plug, and wiggled it in Anne’s anus. She moaned with one of my balls in her mouth, sending vibrations through my groin. Unsure of what to do, I gripped the end of the butt plug and started pulling it out, stopped, and pushed it back in.
As I moved the plug in and out of Anne’s ass, she continued sucking my balls and cock, lifted her head, looked into my eyes, and grinned.
“Keep doing it. It feels amazing,” Anne said.
Taking my cock into her mouth, Anne resumed blowing me. I pulled the plug out of her anus, looked at the strangely shaped device, then pressed it back into her ass. Anne put one of her hands between her legs, rubbing her clit as she took most of my cock into her mouth, pressing the head against the opening of her throat.
It seemed the slight gagging didn’t deter her from blowing me with my cock deep in her mouth. A few minutes later, Anne’s body quivered as her moaning intensified. I didn’t bother warning her as my cock surged, sending semen into her mouth. Anne held my cock between her lips as I sent several streams of cum into her.
I pushed the plug back into Anne’s rectum as she removed her mouth from my cock and moved up, covering my body with hers. I watched her swallow and smile. Pulling her mouth to mine, I kissed Anne. She wiggled when I opened my mouth and shoved my tongue between her lips. I could taste my semen, but it didn’t prevent me from kissing her. After a moment, she lifted her head and smiled at me.
“You’re the only man to kiss me after I blew him. You’re just full of surprises, aren’t you?”
I shrugged my shoulders and smiled. “It just seemed like the right thing to do, Anne.”
“You’re too sweet. You said I gave you your first blowjob. Have you ever given a guy one?”
“No. I’ve tasted mine after jacking off before. It’s no big deal.”
“It is to me, Jeff. None of the men I’ve been with would kiss me after I sucked their cocks even if they didn’t come in my mouth.” Anne grinned. “Another first for us.”
Anne and I began kissing and wiggling together as I rubbed my cock against her mons. When I started getting hard again, she rolled us onto our sides, wrapped her fingers around my shaft, and stroked me.
As Anne slid down my body, I thought she would blow me again. Instead, she reached for her bag, removing a package of condoms and a tube of lube.
Anne encased my cock in latex, coated the condom with lube, then reached behind her, removed her butt plug, and applied the gel to her anus.
“I take it you like anal sex,” I said.
“I’ll let you know. I’ve had plugs and dildos in my ass, but never had a cock.” Anne smiled. “You’ll have to take it slowly. Your cock is bigger than my toys.”
I couldn’t get over how casually Anne talked about sex. I had always considered the subject one you didn’t speak of so freely. Anne was teaching me that a discussion about sex didn’t need to be something to embarrass you.
“You sure seem comfortable talking about sex, Anne.”
“It’s not a big deal, Jeff. How would anyone know what they like or dislike if you don’t talk about it?” It’s only fair to let the person I’m with know if I like something. The same is true of things I don’t like. I don’t want someone to do something I’m unwilling to do. Jodie has taught me that the brain is our most important sex organ. How we think about sex can make it great or bad. If you think something is wrong, there is no way to enjoy it.”
As we talked, my erection began to flag, so Anne cupped my balls and gripped my cock between her forefinger and thumb, wiggling it.
“I think it’s time for us to find out if we like anal sex,” Anne said.
Anne flipped onto her hands and knees, looked at me, and wiggled her ass. I knelt behind her, gazing at her bottom as she reached back, gripped her butt cheeks, and spread them.
Moving closer, I pressed my cock against her puckered anus. As I applied pressure, her sphincter relaxed, and my dick slipped into her rectum. I slowly worked my hips back and forth, pushing my cock deeper into her bowels.
“Oh, fuck, your cock feels good. So much better than any of my toys.” Anne rocked back, matching my thrusts.
As I slid my cock in and out of Anne’s ass, I thought about how sexy it was. I held her hips while I continued moving. She dropped her shoulders to the mattress, put a hand between her legs, and diddled her clit while I ran one hand up her side, gripping her breast.
It didn’t take long for me to move in and out of her harder and faster as my hips hit her upturned ass, making a smacking sound. Anne mumbled and moaned as I continued fucking her ass.
“Harder, fuck my ass.”
“Your ass is so tight. I don’t know how long I can last.”
Anne surprised me when she disengaged from me, rolled onto her back, grabbed her legs behind her knees, and pulled them to her chest. Her ass was open and exposed to me.
“Shove your big cock in my ass! Fuck me.”
I re-entered her anus, sliding in with one push, placed my hands on the back of her thighs, and started fucking her again. Once again, Anne began to rub her clit. As I looked between us, I saw the string of her tampon. She begged me to fuck her faster, and I did my best to grant her wish.
“Yes, you’re driving me nuts. I’m coming,” Anne said.
I felt Anne’s anus quiver around my cock. Her moans and thrashing set me off, and I came along with her. As my cock pulsed, I let out a throaty groan. Lowering my body to hers, I kissed Anne, and she held me as her body vibrated beneath me.
“What the fuck! You made me come as hard as I ever have.”
“You? I thought my asshole would come out of my cock.”
“It would be fitting, wouldn’t it?”
Anne and I separated, got out of bed, and headed for the bathroom to shower. While playing under the spray, we shared kisses and ran our hands over one another.
“I need a drink,” Anne said as we dried ourselves.
“A drink sounds good to me,” I replied.
Anne and I remained naked as we headed downstairs, went to the kitchen, and sat at the table while sipping our whiskey.
When Anne said, “So, which do you like better, fucking my pussy or ass?” I almost spat my whiskey across the table.
“I’m sorry, Jeff. I guess my language upsets you. As I told you, I’m not the same meek, mild-mannered girl you knew in high school. Sometimes, I shoot my mouth off before thinking.”
Unable to decide what to say, I nodded and smiled, realizing Anne’s language or openness didn’t upset me. It made me understand just how nice having a fuck buddy could be. We enjoyed great sex without baggage or expectations other than having a good time. Anne would be gone in less than a month. While I would miss what we were doing, I planned to take full advantage of it as long as possible.
“Anne, nothing could be further from the truth, but I’m not used to it. I wish I had your confidence and the ability to say things as easily as you. To answer your question, I’ll let you know. I haven’t had enough of your blowjobs or fucked your pussy and ass enough to form an opinion.”
Anne started laughing. “That’s fair, Jeff. I hope we can get together enough for you to decide. For me, so far, it’s a three-way tie. Jeff, I’ve learned that having confidence is a learning process. Knowing how to say what you’re thinking without being arrogant is key. You must also be comfortable with the person you’re talking to.”
“So, I guess you won’t be offended if I ask you to go to bed and remind me how well you suck cock?”
Anne downed the remainder of her drink, stood up, and offered me her hand. I finished my whiskey and took her hand as she pulled me to my feet. Hooking her arm in mine, we headed for the stairs.
As we went up the steps, Anne said, “I plan to do something I’ve only done once before after I suck your big cock.”
“What are you planning to do?” I said.
We walked into my bedroom and sat on the bed. Anne kissed me. “I plan to spend the night in bed with a man. You may find it hard to believe, but the only other time I’ve spent the night with a man was the night of our prom when we stayed at the motel.”
“Why haven’t you spent the night with someone else before?”
“As you must know by now, I love sex, but as much as I enjoy sucking and fucking, I’ve never been with a man I was comfortable enough with to spend the night. I’m more than comfortable with you, Jeff. I think you are willing to enjoy doing things without getting clingy. As I told you the first night we got together, I’m looking for a fuck buddy, not a relationship.”
“If I can ask, why are you against a relationship?”
Anne and I stretched out on the bed. She kissed me, moved down, and sucked my soft dick into her mouth. After sucking me for a few minutes, she moved up and kissed me. I put one of my hands on her breast, gently squeezing it.
“I’m not against relationships, Jeff. I’ve been in one for almost five years.”
I started to respond, but Anne put her finger against my lips. “My roommate Jodie and I are lovers. We both enjoy sex with men occasionally, but we only make love to each other.”
“Doesn’t she get jealous when you have sex with someone else?”
“No. Neither of us gets jealous when one of us hooks up with a man. Jealousy is a useless emotion based on mistrust. I trust Jodie, and she trusts me, so we don’t get jealous when the other has a little sexual fun. We both feel jealousy can destroy a relationship.”
“So, you’re not cheating on her?”
“No, not at all. After getting together, I called Jodie and told her all about it. She told me to have fun.”
“Does Jodie hook up with men, too?”
“Sure. As I said, we like cock for fun. Jodie said she was shacking up while she’s home in Texas.” Anne chuckled. “This may sound strange, but I’d feel Jodie cheated if she hooked up with another girl. If she wants to fuck a man, I’m fine with it, as she is with me fucking you.”
“You know what? It doesn’t sound as strange as it would have before we got together. I’m discovering I don’t know shit about relationships and very little about sex.” I kissed Anne and chuckled. “How does Jodie feel about you sucking my cock?”
Giggling, Anne moved down and took my cock into her mouth. As she bobbed her head, she wiggled her body. I stopped her, turned Anne around, and stretched out on my side. I rubbed my fingers on her clit when she started blowing me again.
Anne removed her mouth and said, “My period should finish soon, so my pussy isn’t too messy.”
She covered my cock with her mouth and caressed my balls. I lifted her leg, moved my head to her crotch, and flicked my tongue at her clit, avoiding her pussy and the thin white string. As I licked Anne’s clit, she moaned and tried to swallow my cock. We kept at it until we were sated.
“I can’t believe you licked me while I have my period, Jeff. You’re going to make some woman very happy.” Anne wiggled against me, then kissed me.
Rather than reply, I shrugged my shoulders and kissed her. Anne and I covered ourselves, falling asleep in one another’s arms.
I woke up with Anne snuggling against me. Trying not to disturb her, I got out of bed to use the bathroom. When I returned to the bedroom, she jumped out of bed, grabbed her duffel bag, and hurried past me.
Pausing in the doorway, Anne said, “Come shower with me. I’ll be ready in a few minutes.”
I waited until I heard the shower before joining Anne. She stood in the stall, letting the water cascade over her. I stepped in, wrapped my arms around her, and held her.
After we took turns washing each other, Anne kissed me, reached for the condom she’d brought into the shower, and handed it to me.
“My period is finished. You need to fuck me.”
I ripped open the package, rolled the condom over my hard cock, and hugged Anne. She bent at the waist, placing her hands against the wall as she wiggled her ass. Gripping her hips, I slid my cock into her pussy.
Our morning fuck didn’t take long. I fucked Anne for about ten minutes while diddling her clit. Using my fingers, I was able to get her off before coming. When I removed my cock, she pulled the condom off, leaned over, and sucked my cock.
“We should send Jodie a picture while you’re sucking my cock,” I said.
Anne stood up and giggled. “I have a better idea. We’ll Facetime with her, so she can watch while I’m sucking and fucking you.”
“You’d do it? I was kidding.”
“I think it would be fun, Jeff. Now, as tasty as your big cock is, I need food. Are we going to make breakfast or go out?”
“We can go out. I need to stop and buy more condoms.”
“I brought a dozen with me. Do you think we need more?” Anne said as we dried ourselves with fluffy towels.
“Not for today.” We both laughed.
It was eight thirty when Anne and I walked into a small diner for breakfast. I texted my mom to ask when she’d be home. Mom wrote back, telling me she would see me on Monday. It would give Anne and me Saturday and Sunday alone at the house.
After eating, we got into my car, and Anne moved to the middle of the seat, resting her feet on the hump. She giggled, grabbed my hand, and placed it on her knee.
“I’m not wearing panties this morning.”
I moved my hand under her dress, pressing against her naked pussy.
“Nope, no panties.”
While I drove back to the house, I rubbed Anne’s pussy as she splayed her legs, giving me access. When she told me to finger her, I did.
“Do you have to work today, Anne?” I asked as I diddled her clit.
“No. I’m off until Monday afternoon because they schedule the regular girls on the weekends. I’m part-time, so I don’t get the best shifts. But I still do okay when I work.”
“What would you like to do today?”
Anne chuckled, put her hand on my crotch, and rubbed my genitals. “I think we can come up with something fun.”
I laughed and said, “Is there something you’d like to do other than sex?”
Anne squeezed my hardening cock. “No, not really. I love sex, and sex with…
