Jimmy T’s Family: Bk. 01: Mom



"You're happy it's over with Brianne?" mom asked. I snapped back from my reminiscences.

"I'll finally have some freedom, I might just like--" I started.

"Boys and their freedom," mom immediately shot back, clearly coming down on the woman's side of that eternal male/female debate.

"You didn't think I was ready to settle down with her ... marry her or anything, did you?" I grimaced as I asked the question.

The look on mom's face clearly showed that was the last thing she'd wanted. Her tone softened, "Of course not honey. You're still young. You have years in front of you before you settle down." I smiled inwardly. This was coming from a girl who'd gotten pregnant and married at sixteen.

"I definitely have to get more experience," I agreed with a smile.

I could see that mom wasn't that keen on how I'd said 'get more experience'.

"Heck, I know just about zero about what girls think. What they want. About ..." I stopped for a second, looked shyly at mom, then added, "you know, the sex stuff. I read on the Internet where doctors now say boys should experiment, try different things, different girls, before they try to settle down. It's good for them." It was mom's turn to grimace!

My mother and I had never really discussed sex frankly before. Oh I'd gotten the sex talk from dad when I'd been thirteen or so. And without being too intrusive my parents had followed my various steps up the dating ladder. I'd had three pretty serious girlfriends over the preceding four years and I'd never come right out and told either of my parents what exactly I'd been doing with them.

Mom a couple of years earlier had given me the 'how to treat girls properly' talk. But I'd never actually told her that Bri and I were doing it and, even though I'm pretty sure she knew we were, she didn't ask. And I knew she had no inkling about the six others.

"A relationship isn't just about sex young man," mom tried.

"They show things on the Internet," I replied. "Some of it's weird but some of it is..." I left the sentence dangling. My mom was no prude but I knew she didn't like a lot of the stuff young teenagers could see on the internet these days. More than once I'd overheard her complaining about it to dad or one of her friends.

"You shouldn't be looking at that sort of stuff." We both knew what sort of stuff she was referring to. I didn't say anything for almost a minute before I said my next words. I hadn't practiced any of this beforehand but instead had simply been waiting for this kind of opportunity to arrive.

"Some of it excites me," I said softly.

"What kind of stuff?"

"I'm not sure I'll ever settle down like you and dad ... not with one woman."

"Of course you will!" It was almost an order. "Why wouldn't you?"

"Perhaps it's better not to talk about it," I answered, knowing of course mom would definitely want to talk about it.

"Of course it's better to talk about it. I'm your mother ... Is something wrong?" I could actually see her thoughts flashing across her face considering possibilities. Is my son gay? Impossible! Does he have a physical problem? Something wrong with his penis? She was at sea.

"Do you like sex?" I finally asked, breaking into her ponderings.

I could see she had no idea how to respond. I let her suffer a while before going on."I think I'm abnormal. I think I like it too much," I admitted shyly. "I think about it all the time. Whenever I see a woman I--"

Relief flooded over mom's face. I was okay! "You're a boy ... a teenager ... it's normal for you--" she started.

I interrupted. "But even when I'd be out with Bri, at a party or somewhere, I'd still look at other girls."

"Looking isn't doing," my mom said softly. She figured the worst was over.

"You know I've slept with her, don't you?"

"We'd guessed," mom answered after a moment's hesitation.

Then I surprised her. "You know she's not the only woman I've slept with, don't you?"

"She's not?" mom asked warily.

"Three others," I answered, actually lowering my true count, knowing I didn't want to send her completely over the edge, then I watched as the shock registered on mom's face.

"But... but...but who?" mom stuttered.

I wasn't going to answer that just yet! "There are other things too."

"Other things?" Mom couldn't hide her confusion.

"Sex things. Urges. I can't tell you."

"I'm your mother. You can tell me anything." The words were the start of an unchanging mantra that my sister and I had heard from her all of our lives.

"Anything! Everything! No one in the world loves you more than I do," I said, supplying the next lines all of us knew by heart. Mom raised her eyes in irritation but there was a wry smile on her lips.

"So talk," she ordered. But gently. With love in her eyes. I could feel the warmth of her body against me as we sat side by side on the couch.

I put an arm around her shoulder. Then asked, ""Do you know what an exhibitionist is?" I finally asked back. Worry frowns immediately reappeared on mom's beautiful, normally unlined, thirty-six year old face.


"Showing yourself. Letting people see you... naked I mean... I think I might be one."

"You are not!"

"Have you ever gone to a nudist resort?" I was trying to keep mom off balance.

"A nudist resort? You've been to a nudist resort?" Mom clearly wasn't happy with the idea.

"Not yet. But I'm going to one this weekend."

"To a nudist resort?"

"For the holiday." And as I told her I realised I was going to talk her into going with me. It hadn't been my plan to rush into this. Instead I'd envisioned a slow seduction that might take months. But I couldn't stop the vision of my mother and I walking naked down a crowded beach from forming in my mind. Of being watched by people who'd never guess we were mother and son. People instead who'd look at our naked bodies -- men wanting to fuck mom while their wife's and girlfriend's eyes hungrily took in my penis.

How the heck was I going to convince her to join me I wondered as I watched my mother's face?

I laughed again. Mom frowned. "They have a special celebration on the fourth. A bike ride. A barbeque."

"Who do?"

"American nudists. It's a World Holiday really, not just an American one," I answered. "Actually the whole weekend's a holiday. It's going to be celebrated in over one hundred and ninety-three countries," I added. I just made up the country figure; who the heck knows how many countries there are in the world these days?


No answers for mom quite yet. "Did you ever do it when you were young?" Mom started to shake her head no. "You never even skinny dipped with your friends ... like when you were young?"

"That was different, we were just little girls running around in the dark." I'd guessed right. "There were no boys ..."

"You weren't excited?" Of course she'd been. Who wouldn't have been? I could see mom didn't want to answer. I pressed on. "I'll bet you were. I'll bet you all wondered if there were boys watching you from the shadows."

"We did not."

"What about you and dad? You guys must have gone to a nude beach or something somewhere on one of your vacations. Heck, it's pretty common knowledge that everyone goes naked on the beaches in Australia," I said confidently. I had no idea if my words were true but they sounded good.

"We haven't ... and I've never been to Australia." I couldn't miss the touch of complaint in mom's voice. I realised that she too must have wondered why dad had never taken her Down Under.

"Dad must have. In Australia I mean." I could see mom didn't like the idea.

"Hah! We can't even get your father to go to the seashore when he's home." Another small complaint!

"Well then I'll let you come with me this weekend."

"You are not going anywhere this weekend!" Mom used her mother's 'obey my order or else' voice. It had been years she'd used that tone with me. I had her on the defensive!

"You must have thought about it from time to time. Wondered what it would be like."

"I never have! Do you think I'd wander around naked and let a bunch of perverts see my body? Drool over me."

In answer I reached over and grabbed my computer from the desk and clicked open the Onancock Nudist Society's July 4th 2011 Bike Ride page. Ninety percent of the page was taken up by a picture of a group of naked bicyclists. A shot from the 2010 bike ride.

Then I started clicking through the slide show.

Mom couldn't hide her interest even while trying to show her disapproval of the pictures she was seeing by throwing out comments as the slideshow ran:

"We shouldn't watch stuff like this."

"Look at her!"

"He's got to be seventy!" Said disdainfully as a picture of an old coot with his balls hanging halfway down his legs flashed by. I continued the slideshow.

"That's gross!" A penis painted red, white and blue.

"They should shut down this site!"

"What would their parents say if they knew?" mom finally asked as a picture of three good looking, college aged, nude bikers appeared on the screen. I stopped the slideshow.

"You can't recognise them... they're all painted, disguised, no one would know them," I answered as both mom and I examined the six bodies on the screen. Three great looking girls, three hanging cocks. Mind you none was as big as mine.


"So, you want to come with me this weekend?" I asked it innocently. A cheeky grin on my lips.

"You ... Are ... Not ... Going ... Anywhere ... This ... Weekend!" Back to the Darth Mother voice!

That just about ended our conversation for the night. A couple of minutes later mom was standing up and ready to leave my room. I knew her mind must be spinning. I let her get to the door of my room before yelling out, "love you mom."

She turned back. And after giving me the evil eye for a second she walked back over to me and gave me a big hug. It was a good hug. A hold on while you squeeze kind of hug. And then, just as we were about to break apart I gave my mother a kiss on the cheek. A second one, one she assumed was going to land on her other cheek, just accidently --NOT- landed smack dab on her lips. Her moist lips.

"Sorry," I mumbled, feigning embarrassment when I pulled my lips away from her. A blush sprang onto her cheeks. I let her get fifteen feet back down the hall before I whistled.

She turned. "What?"

"Are you sure you don't have a secret boyfriend? Those pj's show more than even the bicyclists were showing."

"They do not! Now stop your teasing," she denied. Then stamped her foot.

"You look great mom." I said it softly and simply. There was no sexual tone in my voice. Just admiration.

Now really blushing, mom said nothing until a soft, "thanks honey," escaped her lips. Then she turned and hurried away. But I wasn't quite finished.

"Maybe this weekend I'll find out that I'm not really a nudist. I'll get it out of my system, maybe we both will," I said to her disappearing back. Mom didn't answer.

I fucked my hand that night. And guess who I was thinking of when my cock started to spurt out my sperm?

Lying in bed afterwards I wondered who mom was dreaming of. I wondered if my dream mom was walking naked down some beach. And if I was next to her...

Chapter 2 -- Nightime... June 30th 2011

I woke up the next morning knowing that I was going to be able to convince mom to go with me. I was absolutely certain of it. Mind you I knew it wasn't going to be easy. I'd woken early and I left the house before mom had gotten up. And stayed away all day. I wanted her to stew a bit before I gave her my 'nude beach' sales spiel.

I bought two wigs that day. Some body paint. Some weird sunglasses -- a man's pair and a woman's. A wide brimmed hat. A beard. Fake moustaches. More than enough stuff to disguise two nude bike riders. To disguise a mother and her son.

It was just after eleven at night when I finally got home. I'd been in my room for only about five minutes before mom appeared in my doorway. She found me sitting at my desk facing my computer. All I had on were a pair of boxer shorts. I'd been waiting for her. I'd already started up my laptop and opened the home page of the Onancock Nudist Society.

Mom didn't knock before entering my room. "I want to talk to you," she imperially directed as she marched through the door that I'd purposely left open. When I looked up I couldn't miss the fire in her eyes. She'd clearly been saving it up all day. She didn't even noticed my state of undress.

"Good," I said amiably, "I'll need your help." I knew I had to get her on the defensive right away.

"For what?" she snapped.

"My disguise."

"You are not going anywhere this weekend young man!"

I didn't answer her. Instead I stood up and then grabbed the wig I'd chosen for myself from the desk top. She said nothing as I plopped it haphazardly on my head. I put on the shades. "Help me with the moustache," I invited as I geld out the big drooping moustache out to her.

"You look stupid. The wig isn't even straight," she admonished even as she reached out her hands to adjust the wig.

"The moustache is sticky on the back, you have to--"

"I'm pretty sure I can figure out how to put a party moustache on young man," she said sarcastically. And then she did just that. I stepped back from mom the second I was 'moustached'. "Ta da!" I said as I gave her a muscle builder pose. Mom laughed. Which was good.

A second later I was in front of the wall mirror. "I told you, no one would recognise me in a million years."

"I would," mom answered.

"Here, take my picture," I near ordered as I grabbed my camera from my desk. Two minutes later I'd downloaded the picture she'd taken onto my laptop. The guy staring back at me from the screen could have been anybody! "And remember, I'll have paint on my face ... and on my chest ... and on my..."

"Jimmy!" A plea. Full of frustration. But also resignation. Next was the hard part.

"Your turn now," I said as I turned back to my desk and grabbed the wig I'd chosen for mom.

"I am not--"

I plunked the blond wig down on her head. It was one of those hippy style ones. The long, soft blond hairs almost reached her ass. "You always wanted to be a blond," I said with a smile.

"I did not."

"They do say blonds have more fun," I said as I slipped the oversized sunglasses onto her face. A second later a large, straw brimmed had was on her head.


"Look," I said as I turned her to face the mirror. Mom couldn't keep the smile off her lips nor stifle her laugh! "And when you've got a daub of red paint on the end of your nose ... and on your ..."

"I ... am ... not ... going ... nude ... biking ... with ... you! Is that clear young man?"

Which might sound like a rejection to most people but it didn't to me. Without her realising it, her words had already conceded my participation. It was only left to convince her.

Which is what I attempted to do over the next two hours. Back and forth we went. But I was not going to be denied!

"We never do anything together anymore...

"I'll be leaving home soon ...

"The bike ride will just take an hour, then we'll have the whole weekend to do other things...

"It's the Fourth of July... you're supposed to celebrate...

"They've got some great beaches down there... nature trails...

"What are you going to do this weekend anyway? Stay here alone?

"You shouldn't leave me alone with these nudists... you never know what they might ..."

It was the last argument that ultimately convinced mom. I'd roused her motherly protective instincts. She was definitely not going to leave me all alone in the clutches of perverted nudists! And so, just after two-thirty in the morning it was decided -- she'd accompany me to Onancock. We'd have a weekend by the seashore. Maybe take one of the local ferries. Eat some fresh seafood. Relax. Go bird watching. Celebrate the holiday. Of course she was not going to participate in any nude bike ride. Period. Unstated was her hope that she'd be able to convince me not to either.

I started masturbating the second mom was out of my room that night. I used mom's blond wig. But when I finally exploded I took great care not to get one drop of my sperm onto it!

Chapter 3 -- Onancock ... July 1st 2011

"I'm not going on any stupid bike ride and that's final." We were only a block away from home and mom had already started.

"I know, I know," I agreed, keeping my eyes on the road.

"So why'd you bring both bikes?" she demanded. Both moms and my bikes were riding on the rack hanging on the back of the car.

"I showed you last night. It's beautiful down there. The nude bike ride is just for a couple of hours. Then you and I can explore. We'll have three days."

We talked and argued as the miles rolled past. Many of the same arguments we'd had the last two nights.

"I still don't understand why you want to be nude in front of strangers."

"You've never wanted to?"

"I'm married. You're dad..."

"I'll bet you dreamed of doing it. Last night or the night before," I challenged. I was pretty sure that after our talks of the last two nights that something must have invaded her dreams.

"I didn't," mom denied but with little conviction.


We got to the hotel just after ten that night. The room had only one bed in it. A king size one. Which is exactly what I`d ordered over the Internet. Of course I didn`t tell mom that. I even pretended to call the front desk when we discovered it. And then I had a pretend conversation with the dead line.

"They`re completely sold out. Due to the bike ride and the tourists and everything, we can't get another room," I explained to mom once I'd hung up. "I'll sleep on the couch". She wasn't happy but what could she do. We unpacked. I put both our disguises and the paint cans on the desk in full sight.

The bar/restaurant was jammed when we wandered down some twenty minutes later to grab a bite before turning in. And it turned out just about every single person in the room was there for the bike ride. Nudists who were dressed. And excited. The room was alive.

"I don't believe it," mom muttered as we made our way through the throng. Then added, "and they seem like normal people."

"They are," I countered.

"Perverts," mom hissed back as we found one of the last free tables. A minute later, another couple, in their thirties, asked if they could join us. Then, seconds later another couple grabbed the last two chairs at our table. In their twenties they introduced themselves as Colin and Judy McLeod. From Raleigh. It was their first nude bike ride. They'd been on nude beaches before of course. They were so excited. And Judy, a short brunette with big tits, was hot!

As they continued to gush out their history it suddenly hit me that mom and I had no story prepared. I couldn't tell them our real names and I sure as hell wasn't going to tell them who mom was. Quickly glancing over at mom as the second couple, the Clifford's from Northern Virginia, started to tell us their story, I saw that the same realisation had hit her. I mouthed over an 'it's okay' to her and pointed to myself, trying to let her know that I'd handle it.

When the Clifford's had finished their story all eyes turned toward me. And I could see they were curious. The age difference between mom and I had clearly piqued some interest at the table. I decided not to disappoint them.

"I'm Chris," I started, using my middle name even as I continued to try to come up with a story. "I'm a sophomore at Virginia Tech ... engineering ... chemical engineering. From Alexandria ... I mean I grew up there," I said. My obvious nervousness was palpable and the others at the table could sense it -- they were hanging on my every word. They knew something was coming.

"I'm living in Blacksburg now of course. Mrs. Tyler is too ... I mean Bonnie is too," I said as I let a blush spread across my face. I'd used the Missus on purpose. Eyes opened wide. Four sets of eyes flicked quickly from my face to moms and then back. I definitely had their attention! I spun out my story slowly, giving my audience just enough details to let their imaginations have a field day. And I drew mom into the conversation, making her pick up threads I'd started. Things like:

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