A Wee in Venice

I lost my virginity to my mom when I was twenty.

I was going to college at the time and although my studies went pretty well, I was a bit of a wallflower, and had never dated anyone.

I am an only child. During my school years, my parents, both musicians, were often on tour for months on end, and my parents took turns to take care of me, or I stayed with my aunt and uncle if they were both away from home. Also the holidays I would often spend with one of my parents.

My mom, aware that I was alone during the Summer months on campus, had invited me for a week in Venice. I had thought it very sweet of her and I had said yes.

We arrived at Marco Polo airport on a sunny August afternoon and took a water taxi. My mother had rented a beautiful 16th-century apartment near the Rio de Palazzo o de Canonica, owned by an elderly couple. Our room was spectacular, still in its original state, with a painted ceiling, wooden walls, and a marble floor.

Tired and jet-lagged, we had a short meal in a nearby trattoria and went to bed.

The next day we got up early. We had made a list of places we wanted to see, and I had made a schedule to help us avoid the worst crowds. We arrived at the Rialto market at 7am, then stayed in line from 9:30 to see the Basilica San Marco, and spent more than two hours in that most magnificent of churches.

We had lunch in a nice small trattoria and, starting to feel the Summer heat, jet lag and Bardolino, went back to our apartment for a nap.

In the late afternoon we went to the Palazzo Grassi, and after that we strolled to find another trattoria for supper.

During the main course, Mom raised her glass and said: "A toast to you for sacrificing your holiday to your old mother. You can probably think of better company, but I want you to know that I'm having a really good time."

I smiled at her. "Mom, it was so sweet of you to go with me on vacation. Sacrificing my holiday? We're in Venice! And I wouldn't want to be here with anyone but you. So here's to you. My beautiful young mom who invited me to the most wonderful place on earth."

Mom smiled amusedly and said: "That's very nicely said. Still, I'm grateful that you accepted the invitation. Not many twenty-year-olds would care to spend their holidays with their mom. So how about a toast to the two of us?" And that's what we had.

"You don't have to answer me," said Mom, "but are you seeing anyone?"

"No", I said, and I blushed. "I have never even dated anyone."

Mom looked hurt. "I'm sorry," she said.

We were silent for a while.

"How come you have never dated anyone?" asked Mom.

"I don't know. I feel really clumsy around girls. I become hyperconscious of everything. Don't know where to leave my hands, and I'm thinking every few seconds if I'm making the right amount of eye contact. I don't know a good opening sentence to begin with."

"Opening sentences are so overrated", said Mom. I've heard them all: 'Haven't we met before?' or 'You have the most beautiful eyes I've ever seen!' They're such a turn-off. I never dated guys who talked to me like that. It's better to be a little ambiguous. Start with friendly conversation and don't make your intentions too clear. Girls have hunting instincts too. If they think you're up for grabs, you're less desirable to them."

I nodded, as it was certainly good advice, but wasn't too sure if I would be able to put it into practice.

Mom said: "I'm sorry, I don't want to make you feel bad. Let's talk about something else."

"It's OK", I said. And we changed the topic of our conversation.

Back in the apartment, we took turns to shower and went to bed, a letto matrimoniale. The advertisement had mentioned two single beds, but we had been too tired to protest.

I was lying on my back and Mom on her side, looking at me.

"Can I give you a hug?" Mom asked.

Even though I felt a little surprised and awkward, as I was only wearing shorts and a T-shirt, and Mom only a nightgown, I nodded.

Mom moved to me, put her arms around me and her left leg over my mine, and gave me a sweet, loving kiss in the neck.

Sensing her soft warm body under the silk nightgown, I involuntarily grew a giant erection and froze.

Mom felt my unease and moved back, but in doing so, accidentally brushed the bulge in my pants with her hand. "Sorry," she said softly. I muttered: "It's OK."

There was a moment of awkward silence.

Then, Mom asked: "Shall I... help you with that?"

The thought of Mom "helping" me both shocked and aroused me. The arousal won. "Are you sure?"

Mom put her arms back around me, firmly pushing her body against mine. She moved down my shorts, revealing my fully erect penis, and started to slowly masturbate me. I turned around and we looked each other in the eyes. Mom smiled at me and I smiled back to her.

She guided my right hand to her left breast and I started fondling it.

We kept looking each other in the eyes while we caressed each other.

Despite the absurdity of the situation, my nervousness fell away. Being intimate with Mom felt good. I did not have to prove myself to her, and she loved me the way I was.

I gathered all my courage and softly asked: "Mom, will you make love to me?"

Mom stopped masturbating me for a moment and looked me in the eyes.

"Only if you want it too," I said.

Mom hesitated. Then, she took off her nightgown and undies. I saw Mom naked for the first time since I was a child. I had always thought of her as pretty. Nude, she was stunningly beautiful.

"O Mom," I gasped. Mom smiled at me, and helped me out of my shirt. We lied down and held and caressed each other, breathing ever more quickly.

After about twenty minutes, Mom sat on top of me, and guided my penis to the entrance of her pussy. It wouldn't go inside.

"I'm a little tense," said Mom.

Mom started rubbing her clitoris with two fingers while she kept pushing her pussy gently against my penis. I felt her arousal fluid running down my penis, and I slowly slid inside her.

Mom rode me slowly and for the first time I experienced the delightful sensation of being inside a woman. It felt so overwhelming that I came close to an orgasm almost immediately. I gently put my hands on Mom's hips to make her slow down. She stopped riding me for a moment, guided my right hand to her clitoris, and helped me stimulate her. Once I understood how she wanted it, Mom resumed riding me, her hands on her knees. We kept looking at each other. "You can look at me", said Mom. I knew what she meant and admired her long smooth blond hair, her large round tits, her lovely hourglass-shaped body, and her soft, moist, hairy pussy. But we mostly looked each other in the eyes. Whenever I was close to orgasm, Mom sensed it, slowed down, then continued riding me.

After a while, Mom started to breathe ever more quickly. "Come inside me," she said, and we climaxed together. Mom started sobbing while I squirted large loads of sperm inside her, five, six, seven times.

Mom lied down on top of me and we hugged each other.

I wiped off Mom's tears, kissed her on her lips, and caressed her hair.

"Are you allright?" I asked Mom.

"I'm OK. And you?"

I nodded.

Mom smiled through her tears, and I said: "You are making me so happy, Mom. I love you."

"I love you too dearest."

I held Mom tightly as we cuddled and fondled each other.

"Mom, do you regret it?"

Mom stared at me for a moment, then shook her head. "No my love."

I was still inside her and after a while, I got a new erection. Mom lied down, and let me on top, and I fucked her once more, slowly and intensely.

We made love five or six times that night. Then we went to the bathroom and showered together. I washed Mom's vagina, and she washed my penis. We went back to bed, and slept naked in each other's arms.

The next day we slept late, and ordered lunch in our apartment.

After lunch, we undressed, and went to bed again to make love.

Mom gave me a sweet kiss on the mouth. I hesitated and Mom noticed.

"It's OK if you don't want to kiss", she said.

"I'm sorry Mom. I just think it's strange to kiss with you."

Mom smiled amusedly. "You think kissing your Mom is worse than fucking her?"

I chuckled. "Touché."

We tried a tongue kiss. It felt really awkward.

"That is weird", said Mom. "but maybe it just takes a little getting used to".

Mom caressed my face with both her hands and gave me a deep, loving tongue-kiss, while I stroked her face, hair, back, buttocks, and tits. After twenty minutes of intense kissing, the unease went away. We kissed ever more deeply and intensely while we held and stroked and caressed each other.

We were both red-faced from arousal. Mom was soaking wet and my penis was throbbing and painfully stiff.

"I want you inside me," said Mom.

Mom sat on top of me and I softly pushed the tip of my penis between Mom's labia. We tongue-kissed and I felt her nipples on my chest . Her vagina was open and so wet that I slid inside her very easily, all the way in.

Mom made us sit upright. She was sitting on my legs and moved her hips around, making my penis slide back and forth inside her vagina, while we tongue-kissed intensely. I couldn't penetrate Mom very deeply this way, but I loved holding her close, tongue-kissing her, feeling her nipples, and stroking her back and her hair.

I wanted to climax with Mom together but after a few minutes, my senses became completely overwhelmed. "Mom, I'm coming." Mom kissed me even more intensely, contracted her vaginal muscles, and I felt like bursting inside her, filling her with load after load of sperm. Mom closed her eyes and bit her lower lip, moaning softly.

"I'm so sorry Mom, I wanted to come together with you."

"Don't worry about it," said Mom. She smiled at me. "That was lovely."

We showered together, then went back to bed.

I couldn't stop looking at Mom, and I knew I had deeply fallen in love with her, and wanted to make her happy.

"Mom", I whispered, "will you teach me how to lick your pussy?"

She smiled. "Of course."

Mom lied down on the pillows, spread her legs, and started teaching me.

"You need to stimulate me in two ways at the same time. While you lick my clitoris here, I need your index and middle finger inside me, like this. But first, we need to cut your nails really short and polish them smooth, so that you won't injure me. Give me your hands."

She reached out for her nail clipper and nail file and made my nails completely smooth.

"OK let's get going," Mom said. "First foreplay."

We did twenty minutes of foreplay. I caressed her face, her hair, her back, her arms and her feet, and licked her nipples. Then, she took my head in her hands and guided me to her pussy.

Mom's labia were swollen and wet. I started licking her pussy. "A little higher. More pressure. Too fast." She kept giving me guidance until she felt silent. Then, she moaned softly. "This is lovely. Now let's work on the fingers."

I gently pushed my index and middle fingers inside Mom's vagina, careful not to hurt her.

"Don't worry", she said, "you're not hurting me. Now, push your fingers downwards. Not deeper, you're already all in. Right. Now, move them like this." She took my hand and we exercised until I understood how she wanted it.

"OK", she said, "now, you need to use your tongue and your fingers at the same time. I will guide you. Do not rush and do not stop. A woman's orgasm comes in waves."

She laid back and held my head in her hands while I licked her and moved my fingers inside her vagina exactly as she wanted it. She moved her hips around so I knew how fast she wanted me to go.

After half an hour she reached a gigantic climax. "God!" she cried.

Mom pulled me up, and we held each other tight. "Oh God, this was good," said Mom. The tip of my penis pushed against the entrance of her vagina." "I know you want in," said Mom, "but do it now and it will really hurt. I'll give you oral in a minute."

"No rush, Mom", I said. "I enjoy seeing you so happy."

Mom looked at me for a long time, stroking my hair.

"Love me," she said.

I gave Mom a deep, intense, salty kiss, and put all my love for her in it.

"Yes," said Mom. "You do love me."

We cuddled and kissed and stroked each other and I wanted to be Mom's lover forever.

A little while later, Mom let me lie down on the pillows, took my stiff penis in her right hand, and looked at it curiously.

"Geez, I hadn't noticed you were that big. Six inches?"

I chuckled. "I never thought of measuring it Mom. Underwear doesn't come in penis sizes."

Mom laughed. "In this case, perhaps it should."

Mom gently pulled down the foreskin and she started kissing and licking and sucking my penis and my balls. She did not need any guidance. I held her head in my hands and caressed her hair while she made me reach my climax. I pulled out just in time and ejaculated on my own belly.

Mom licked the sperm from my belly and my penis, then lied down next to me, and again we held each other closely.

"Next time you can come inside my mouth," said Mom.

"I don't think that's nice, Mom," I said.

"I like it. And I love the taste of your sperm," she said. "But it's sweet of you to be so considerate."

We cuddled for a while without saying anything.

"May I ask you something intimate?" asked Mom.

"Yes," I said.

"How often do you do it?" she asked.

"You mean -- "

"Masturbate," she said.

I blushed intensely.

"Two or three times a day," I whispered.

"Where do you do it? You don't have a lot of privacy in your dorm room."

"If Lawrence is there, I do it in the shower. When he is with his girlfriend, I do it in the room."

"Do you phantasize or do you look at porn?"

I blushed even more.

"You don't have to tell me. But it's OK to tell me. I won't judge you."

"I phantasize about professor McNair often. And I have some magazines."

"What is professor McNair like?"

"She is our best teacher. She is really pretty and she is always nice to me."

"And let me guess. She has beautiful long hair, big boobs and wears tight blouses and high-heeled shoes."

"None of that," I said, and then, softer: "Apart from the boobs."

Mom laughed. "Don't be embarrassed. So what do you phantasize if you think of her?"

"A different story every time. Last time I thought about how we would go hiking into the mountains together, walking hand in hand, and talk and have fun."

"I guess she'd be wearing a tight body con dress and no undies and no bra, and her tits would bounce as she walked," said Mom.

I turned red. "Erm, right. And we would find a nice picnic spot and we would start making out and have sex."

"That sounds really nice," said Mom. "Maybe you should invite professor McNair for a holiday."

"Not a chance," I said, "she's married."

"I'm married," said Mom, ironically.

I laughed.

"Tell me about the magazines. Do you jerk off to them?"

"Geez Mom, really?"

"You don't have to tell me. I'm just curious. It turns me on to hear you talk about it."

"OK," I said, but it took me a while before I could answer.

"I have some Penthouses."

"Penthouse? Is that soft or hard core?"

"Soft core I think. There's no sex in them, just nude women."

"So what do you do? You look at the nude pic and you jerk off while you think of fucking them?"

"Yes."

"So where do you buy the magazines?"

"I buy them at a newsstand. A different one every time. I don't want them to remember me."

"So buying a Penthouse embarrasses you?"

"Yes", I said. "Especially if the seller is a woman. Sometimes they look at me with such contempt."

"Why are they selling those magazines then?" That was a fair question.

"So you don't mind me jerking off to nude pics?" I asked.

"Not at all," said Mom. "Everyone has sexual phantasies. You can't help what arouses you. By the way how did you choose Penthouse? Did you try different magazines? I see so many of them at the newsstands."

"I tried several. Playboy is a bit too polished and soft, it doesn't turn me on enough. Hustler is more explicit and vulgar. Penthouse is nice, and, well, hot."

"What do you mean by hot?"

"The women are really beautiful, and they are very beautifully photographed. And er,..."

"Yes?"

"They show pussy."

Mom laughed. "What is it with guys and pussy? I think a vulva looks so unattractive."

"Really?"

"You don't think so?"

"I think yours is so beautiful. It looks like a rose. I think roses are pretty."

Mom giggled. "You are such a romantic," she said.

"Let me show you. Can I look in your make-up bag?"

"My make-up bag?" asked Mom. "Sure, I have no secrets for you. Why?"

I got up, opened the make-up bag at the dressing table, and took out her hand mirror.

"God, no," said Mom.

I stepped back into bed, and sat behind Mom, my face right next to hers, and held the mirror, and we looked at her vulva together.

I opened up her labia a bit with my index and middle finger. "Look, doesn't your vulva like a rose?"

Mom looked, but wasn't convinced. I opened her up a little further.

"Hmmm. Maybe a little bit."

Mom felt my hard-on and smiled. "You do love my pussy, don't you. And I love to feel you inside me. Shall we try doggy style?" We made love once more and built up a mighty orgasm together.

After a while, Mom got out of the bed and said, "Mind to go outside for an errand?"

"Sure. What errand?"

Mom didn't answer.

We dressed and went outside. It was late afternoon, hot and humid.

"Where are we going?" I asked.

"To a newsstand," said Mom.

It took me a while to realize what she had just said.

"A newsstand? Seriously?"

"Of course. I want to know what I'm competing against."

I felt embarrassed in the extreme. Yet the thought of Mom buying a nude magazine turned me on.

We found a newsstand. The seller was a woman in her fifties. Oh God.

"Penthouse magazine, per favore", said Mom cheerfully.

The woman didn't even flinch. "Edizione italiana o americana?" she asked.

Mom turned to me. "What, they come in different editions?" I was too embarrassed to speak. "Both," said Mom to the lady. The lady mentioned the amount, put the magazines in a thin brown envelope and Mom paid.

We went back to the apartment and sat on the bed together. Mom opened the American edition and browsed to the first nude pics. It was a stunning beauty with curly red hair in a room with antiques. Mom looked at the first picture. "She's a knockout. I would have sex with her." She turned the page.

The model was sitting on a grand piano, with her legs wide and her pussy open, wearing sharp high-heel boots going all the way up over her knees.

"These boots are just for photoshoots, right? You couldn't possibly walk with them."

She looked at me, curiously.

"Have you got a thing for boots?"

"I think she's really hot," I said. "But I still worry what you think of me for jerking off to magazines."

"I want to know all about your sexual phantasies. Don't worry. I think you have excellent taste. These pictures are really nice." She looked at the magazine again and turned the page.

There was a close-up in soft focus where the model pulled a pearl necklace out of her vagina. Mom gasped. "Geez, that's really in your face," she said.

"But effective", she continued. "God, I'm soaking down there."

She looked at me again. My heart was racing.

"Are you OK?"

I was too aroused to speak.

"I would have sex with you, but I can't compete with this redhead," Mom teased.

"Mom, I'm going to explode," I muttered.

"Come here my love," said Mom. "If you need to explode, do it inside me."

I quickly unzipped Mom's dress and took off her bra and undies. I looked at her pussy and saw that her labia were swollen, open and wet. I took off my shirt and pants, revealing my fully erect penis.