The Mammoth Book of Erotic Confessions (39 page)

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.

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.

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 hold 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.

I turned her over and thrusted in and out of her in perfect rhythm. Her fingers were gently tickling my back. Her eyes were closed. She was moaning. Head moving back and forth. My hands were
getting lost in her hair. I was gently kissing her neck and chin, every once in a while biting her flesh. Her hands travelled lower and lower down my back until they clutched my butt. Her hands
stayed on my butt for the rest of our love-making, pinching and squeezing the flesh. It drove me crazy.

I could feel myself reaching the point of no return. I picked up speed and thrust harder, deeper and faster inside Grace. Her moans became louder and more high-pitched. Her grasp became
stronger. My hips were working like the pistons of a machine. Finally, I couldn’t hold it in any longer and I had the most intense orgasm of my life. I let out a groan and collapsed on top of
her. She ran her fingers through my hair and kissed my shoulder. I rolled off her and held her in my arms, naked flesh against naked flesh, for half an hour.

“That was great,” I said.

“Yeah.” She kissed my chest. “I had a lot of fun. Thank you.”

“Same here.”

A lot of people may not understand how a nineteen-year-old boy could have sex with a woman who was old enough to be his grandmother. I can’t explain it myself. There was something about
Grace. Something indescribable. I must say it wasn’t a one-time thing we had. We would get together a few times a week and talk for a while before going into the bedroom where Cammy
couldn’t disturb us and have sex for a few hours. I am thankful that Grace came into my life. That she was brave enough to respond to an anonymous ad online and that I was brave enough to
follow it through. I look back on the time I spent with her now and I smile.

Rebecca, Stockton-on-Tees

Galloping along the ridge I couldn’t help but remember the last time I came along this way. That was about three weeks ago when Janet had cried off the afternoon ride.
I’d soon got over it though because it is so gorgeous up here when the weather is this good and I really prefer to be on my own anyway – that way I can appreciate it all. Janet would
just have kept chattering on about David, her latest boyfriend, and would have spoilt the peace. Days like this are too good to be spoiled by selfish girlfriends who only want to talk about
themselves or other things, which of course involve them. I relax into Copper’s rhythm and let my mind wander back to that momentous day.

Copper had been quite frisky and had been jumping all over the place so once we’d got up to the ridge I’d just given him his head to let him burn off some steam. Suddenly one of the
“bushes” a couple of yards ahead moved and Copper jumped off to the side, unseating me, and I flew through the air and landed in a humiliating and very painful heap. As I was trying to
catch my breath I realized the “bush” was now walking over to me.