The Mammoth Book of Erotic Confessions

by Barbara Cardy

  Donovan helped me unbutton my denim shirt, my hands shaking like a teenager showing his buddy his hidden stash of gay porn mags and wondering what would happen next. Donovan pushed my shirt off my shoulders, grabbed my pale pecs in his hot brown hands, and licked at my cherry-red nipples. I moaned as he twirled his thick tongue around first one nipple and then the other, as Skeezer hard-sucked my cock, almost pulling me off my feet with the intensity of his blow job.

  Shivers of delight raced up and down my spine, like batters rounding the bases and heading for home, my balls tightening with imminent release. Donovan bit into a flaming nipple and pinched the other; Skeezer squeezing my tensed sack as he wet-vacced my cock.

  “I can’t take any more,” I yelped.

  “Swing for the fences, Mal,” Donovan urged, mouth full of nipple. “We all do.”

  He stuck two of his fingers into my gaping mouth and I anxiously sucked on them, Skeezer taking me down to the matted hairline and back up again, over and over, sending me flying. I trembled out of control and my balls boiled over and my cock exploded. I blasted Skeezer’s pretty mouth full of sizzling sperm and whimpered like a spoiled millionaire athlete, my body jolted by wicked orgasm again and again.

  Skeezer took everything I had to give, like a true teammate, swallowing hard and sucking harder, milking my pulsing cock, draining my balls. And when I’d finally, blissfully, spurted my last dollop of sticky sunshine, I would’ve tumbled to my knees in gratitude and exhaustion had Donovan not held me up by the nipples and whispered in my ear, “Now you have to prove that you’re a team player.”

  My eyes fluttered open and I stared at Blondie and Red staring back at me, cocks in their hands and grins on their kissers. I glanced down at Skeezer gently stroking my spent and slimy prick, noted the evil grin on his puffy lips. “I’ll . . . I’ll put out for the team,” I gasped.

  They were all over me like a guy getting mobbed at home plate after belting a game-winning dinger. They stripped me clean of clothing. Then the lube came out, Skeezer gleefully greasing my asshole and Donovan’s cock. Sufficiently slickened, Donovan stretched out on a hastily unfolded lounger, long and hard and glistening in the hot sun. He gestured at me to stretch out on top of him.

  I gingerly climbed onto the man’s smooth, awesome physique, facing away from him, facing the crowd. His heavy cock squeezed up between my legs and pressed against my balls. Then he gripped my hips and pushed me upwards, easily holding me there with one hand while he grabbed his cock with the other and pushed its head into my butt cheeks, probing for my opening. I spread my trembling legs and positioned my feet, and Donovan’s bloated hood quickly broached my asshole and punched up inside. He lowered me back down, burying his cock in my ass in one slow, sensual motion.

  I closed my eyes and groaned, my body flooding with heat, a hard young cock up the ass feeling so very good, so very right. But I wasn’t expected to field just one cock. Blondie and Red stepped up to the plate, on either side of me, extending their erections towards my open mouth. Donovan had a secure grip on my waist, raising and lowering me on his cock like a pennant on a flagpole, so I reached out and grabbed on to Blondie’s long cock and started stroking, pulled Red’s thick little penis into my mouth and started sucking.

  The fearsome foursome went on like that for an amazing few minutes, Donovan impaling me while I alternately tongued and tugged Red and Blondie’s cocks. But then Skeezer got in on the action, grabbing my flopping cock and filling his mouth with it again. He got me hard as before, then greased the both of us up.

  Donovan slowed his ass-pumping so the pink-haired guy with the rock star body could straddle the two of us, facing away from us. I knew what to do and I did it, plugging my numb cock into Skeezer’s tight little hole, sinking deep into his quivering bum like a spike into the warm, wet sod.

  I could hardly believe what was happening. Here I was, a respected, middle-aged business executive, getting reamed by one young stud, reaming another, while sucking and jerking off two others – in blazing backyard America. It pays to participate, I guess. And being a good sport certainly helps.

  I licked and sucked and pulled on Red and Blondie’s cocks as best I could, as Skeezer joyfully bounced up and down on my cock, as Donovan surged his cock back and forth in my tingling chute. It was a hard, intensely pleasurable workout, and I was soon wetly rewarded for all my efforts.

  Red bellowed like he’d been hit by a pitch. He grabbed my head and poured molten semen into my mouth, just as Blondie started shaking on the end of my hand and I jacked his hot seed all over my face and his buddy’s groin. And the sight and sound and smell of those spurting males quickly set off my two bum-buddies. Donovan dug his fingers into my slick flesh and grunted, unloaded in me, blasting my ass full of come. Then Skeezer shook like a stadium full of fans and fell back against me, sperm jetting out of his hand-cranked cock.

  It was left to me to bat clean-up, my body arching and my brain melting as I rocketed spunk into Skeezer’s dancing bum, as I hand and mouth and ass milked my teammates. A guy’s never too old for this game.

  TIRED OF BEING A VIRGIN

  Joe, Wheat Ridge

  Sex with a stranger. A woman who tells you her name five minutes before you fuck her. A woman that you have never met before and, the chances are good, you will never speak to or see again. That is how I lost my virginity when I was nineteen years old.

  I’ve never been very comfortable around girls. I have many girls that are friends and I have no problem talking to them but to make that next step from friend to girlfriend or even just to fuck buddy, is the hardest thing in the world for me. I had wanted to have sex since I was fifteen. All of my friends were doing it, talking about it, enjoying it. I wanted to get in on the action. The only problem was, I didn’t know how to ask any of the girls I knew if they wanted to sleep with me. Do it wrong and I could royally fuck up some pretty good friendships. I was such a wreck. Then when I turned nineteen, I finally decided that it was time. I was tired of being what felt like the only member of the V. Club.

  The most logical way for me to go about losing my virginity, at least in my mind, was to put an ad on one of those online personal sites. I figured that being the only sexual partner I had ever had was my left hand I would be pretty bad at actual fucking and if I was able to lose it to someone I didn’t know and would never have to look in the eye again it would be easier for me. So I summoned up all my courage and posted my ad:

  Tired of Being A Virgin: I am a nineteen-year-old guy; five foot eight, one hundred thirty pounds. Average build. Smooth chest, arms, legs, pits and ass. Trimmed down below. Nice sized cock. Big full balls. Shoulder-length brown hair. Blue eyes. Oh yeah, I’m also a virgin. I am looking for a girl to pop my guy cherry. I am unconcerned with age, race or looks, however you must be totally disease free. I just want to fuck. If you’d be interested in breaking in a virgin, give me a shout. I do have pics available if you want to see what I look like. Hope to hear from you soon. Joe

  I reread my ad 100 times. I wanted to make sure that I said all I wanted to and that it was perfect. I took a breath and submitted the ad. My heart was pounding. My breath was rapid. I was sure that no one would respond. After all, how many girls want to be with a guy who probably won’t be able to last long?

  Later that night I checked my email and almost fainted when I saw that someone had responded to my ad. I started sweating and my heart felt like it was about to burst out of my chest as I opened the email. I smiled as I read the letter. It was full of sweetness. Innocence. A little bit of fear at responding to an ad online. I printed it out and still look at it from time to time when I’m feeling down and need something to put a smile on my face.

  Dear Joe,

  First let me say that I have never responded to an ad like yours before so I am a little nervous. Allow me to introduce myself. My name is Grace. I am going to tell you my age right now, just in case it turns you off. I am fifty-five years old. My husband died about six months ago and,
even though I thought it would never happen, I have started having sexual urges. I have always had a fantasy of being with a younger guy and I thought maybe you and I could help each other out.

  I am five foot four inches tall and weigh 115 pounds. My hair is long, stopping at my lower back, and grey. As per request, I am totally disease free. [This part made me smile. It seemed like she had a good sense of humour.]

  I am enclosing a photo of myself. If you are interested in getting together, let me know. If you are interested, would you mind sending me a photo of you?

  Take care and if I have offended you I am sorry.

  Yours, Grace

  I downloaded the photo and was pleasantly surprised at the woman I saw. She was really beautiful. She didn’t look fifty-five. If I had just seen her on the street, I wouldn’t have guessed that she was over forty.

  I didn’t even need to think. She was perfect. I immediately responded to her.

  Dear Grace,

  Thank you for responding. I really liked your photo. You are very beautiful. I am interested in meeting and am enclosing a photo of myself. Let me know when would be a good time.

  Talk to you soon, Joe

  I felt myself shaking slightly. This was it. I knew it. I wasn’t going to be a virgin for long!

  Grace and I made plans to meet the next day at a small coffee shop that was across from my house. That morning as I was picking out my clothes, I was a nervous wreck. I didn’t know what a guy was supposed to wear to lose his virginity; something comfortable I guessed. No need to overdress. I settled on a pair of jeans, a black T-shirt and my Yankees hat. I walked over to the coffee shop, getting there fifteen minutes early so I would have time to calm down.

  I sat down at a table by the window and tried my damnedest to concentrate on breathing evenly. I didn’t want to appear scared. What if that turned her off? As I sat at that table, my mind began to wander into territory that I didn’t want to think about. What if she didn’t show? What if she smelled? What if I did? What if she didn’t like me? What if I was bad in bed? What if I couldn’t get an erection? Or hold one? What if I came too soon? What if she was a psycho? What if she had a disease? A knife? A gun? Stop! I commanded myself. If you get yourself all worked up then you’re going to ruin this and you will be fucked. And not in the good way.

  I saw her walk through the door and choked on my breath. Her picture didn’t do her justice. She was really, really beautiful. Her hair was flowing freely. She was wearing a pair of white shorts that showed off her long legs; legs that could rival those belonging to the most desirable models. She was wearing a tank top that clung to her breasts, proudly displaying them. She saw me, smiled and walked over. I got up when she reached the table.

  “Joe?” Even her voice sounded young.

  “Grace?” I tried to match the calmness in her voice.

  “Have you been waiting long?”

  “No. I just got here. Did you have any problems finding the place?”

  “No. I live five minutes from here.”

  “Really?” I asked surprised. “Wow. We’re neighbours.”

  She laughed and we sat down.

  “So . . .” she said. This made me feel a little better. At least she was nervous too.

  “Yeah . . .” There was a pause between us for a few minutes. “I want to thank you for responding to my ad. I didn’t think anyone would.”

  “To be honest, I was really scared about it. I’ve never done anything like this before. My husband, he was the only person I’ve ever slept with. When he died, I didn’t think I would want to sleep with anyone else but . . .” Her voice trailed off.

  “So, do you maybe want to go back to your place?”

  I don’t know what made me ask that so soon. I hadn’t planned on it but it just seemed like the right time.

  “I’d like that.” She smiled at me.

  It turned out that Grace only lived a few blocks from my house. I liked her house. It was a small, one-storey ranch with a neatly trimmed yard and small flower garden out front. We walked inside and I was immediately attacked by a small dog who resembled a hairball. Even the dog’s face was completely covered in fur leaving barely enough room for two brown eyes to spy on the world.

  “Cammy, be good,” Grace told the dog. “Sorry about that.”

  “It’s all right. I love dogs.”

  I sat down on the couch. Cammy jumped on my lap and vigorously licked my face. I smiled and petted the dog. “How old is she?” I asked.

  “Four months. I got her because the house was too lonely. She’s a good girl.”

  She sat down next to me and petted her small dog. We talked for a little bit, getting to know each other. She told me how she had met her husband. What he had done for a living. What she had done for a living. I told her about what I was studying in college. What I hoped to do with my life. Before we knew it we had run out of things to talk about.

  “So,” I said, throat suddenly dry, “where were you thinking of doing this?”

  “Would it be OK if we went into the bedroom? Cammy won’t bother us.”

  “I’d like that,” I said. “Would it be OK if I get a glass of water?”

  “Sure.”

  She went into the kitchen and got me a glass of water. I drank it with the intensity of a man dying of thirst.

  We went into the bedroom. Grace closed the door. My hand was in hers. She led me over to the bed. We sat down.

  “I really appreciate you doing this,” I said stroking her hair.

  “Same here.” Her voice was soft.

  I leaned in and kissed her. Her eyes were closed. Mine were open. Our mouths were joined. Her fingers were lightly, tentatively, caressing my back through my T-shirt. My hands were rubbing her shoulders. Our hearts were beating wildly. We were scared. Excited. Nervous.

  “Get on top of me, Joe,” she whispered softly while running her fingers through my hair.

  Gently I eased her onto her back. We continued to kiss. My body was on top of hers. Our hands continued the exploration of each other’s body.

  My heart started pumping faster when she removed my T-shirt. Her hands caressed my back. My body was hot with desire; I wondered if she could feel it. It wasn’t long before I had removed her shirt. My mouth travelled lower down her body. My lips made contact with her fleshy cleavage. Gently I kissed the tops of her breasts. Sucking the flesh. Licking it. I liked the taste of her. Her own skin was just as hot as mine. With shaking hands, I removed her bra. For a woman pushing sixty she had really nice breasts. They were perky. Didn’t sag. Her nipples were erected. Gently I took her breast in my hand and placed it in my mouth. She moaned with pleasure and clutched my hair tightly as I sucked on her breasts, teasing her nipple with my tongue.

  “That feels nice,” she moaned, eyes closed.

  I smiled and went to work on her other breast. Grace squealed and wrapped her legs around my waist. I gently rubbed my body against hers. My hard-on was throbbing, wanting to burst out of my pants. I was sure it would explode.

  I planted a trail of kisses down her stomach. I unbuttoned her shorts and pulled them off her hips along with her panties. I started to sweat a little at seeing her nude. Her pubic hair was curly and neatly trimmed, just beginning to turn grey. I rubbed her legs, hoisted them over my shoulders and lowered my face to her vagina. I started out by kissing her flesh. Her legs wrapped themselves tighter around my neck. She moaned out my name. I gently sucked and bit the flesh. She shivered slightly when I stuck my tongue inside her. I thrusted in and out of her vagina. I flicked my tongue against her, stimulating her clit before burying it deeper inside her and swirling it around her.

  “I thought you were a virgin,” she moaned.

  “I rented a porno last night so I would know what to do,” I confessed.

  She laughed. I continued my oral pleasure on her for about another fifteen minutes, then it was my turn. She rolled on top of me, unbuttoning my pants and discarding them and my boxers. Timidly she took a h
old of my penis.

  “You have a really nice body,” she said gently stroking my penis and massaging my balls.

  “Thanks. So do you,” I said gently fingering her.

  She lowered her head and sucked on my balls, licking them with her tongue before opening her mouth and swallowing me whole. She used a variety of techniques to get me off. She would bob her head up and down before kissing the tip of my penis and then licking the length up and down like an ice-cream cone.

  “You’re good at that.” I smiled down at her, enjoying the sight of my penis in her mouth.

  “Thanks.” She smiled up at me. “I rented a porno last night too.”

  “Come here. Get on top of me. I want to do the sixty-nine.”

  She got on top of me, giving me a great view of her butt and, let me tell you, it was a butt that most twenty-year-olds wished they had. We licked, sucked and bit each other for about twenty minutes.

  “I want you inside me, Joe,” she said, out of breath.

  “Do you want me to wear something?”

  “No. Unless you want to.”

  I didn’t. She mounted me and guided my penis into her vagina. We moaned in unison as we got used to the feel of each other. I enjoyed the feel of her wrapped around my penis. Slowly, she began to ride me. Up and down. Up and down. It was hypnotic watching her breasts jiggle and her vagina going up and down on my penis, wet with her juices. Her hands were on my chest, playing with my nipples. I had my hands around her butt, every once in a while slapping the flesh. We were moaning. My back was arching every few minutes.