Running Through The Family

Mike loses his virginity then discovers how casual his family are about sex

My name is Mike and I’m here to tell you about my sexual adventures with my family members.

It’s a remarkable story and you can choose to believe as much of it as you want. I never planned it at all, and things started very slowly. I was a shy kid, and I was almost twenty when I lost my virginity. Shameful really. I had been going steady with a girl, Michaela, for about four years. She was religious and was waiting until she got married before she had sex, which I respected. Unfortunately, it seemed that I couldn’t wait and took an opportunity to lose my cherry with a random girl. I was working for a printing company. It was a warehouse job. I graduated high school but was never smart enough for college, but I as physically fit so signed up to this job straight from school. It paid quite well so it was great for me at the time. My second summer working there, it was a hot one I remember, and the company took on a bunch of interns in different parts of the business. They were high school dropouts mostly and taken on by the company to fill a quota of some kind. Anyway, one lunchtime a couple of these interns sat next to me with their packed lunches. Both girls and both around eighteen. One was very quiet and the other extremely chatty. She asked me lots of questions about her job, me and my girlfriend. After finishing her food, she asked me to follow her. I was curious and she had a very insistent manner. She led me through a large open-plan office, which was almost empty at lunchtime, into a kind of stock room.
“Want to fuck me?” She asked. I was taken aback but before I had any time to answer she had already removed her top. Instinctively I did the same. We kissed for a bit and then she took her panties off and threw them to one side. She then undid my belt and pulled my jeans down. I could hardly believe the casualness of everything. I may have been a virgin, but I had a decent idea of what I had to do. I took my cock out and played with it for a bit until it was stiff. She leant back against some shelving and lifted her skirt. I fumbled between her legs but was hopeless and eventually she had to guide my cock into place. I was so excited, and it felt so good. I fucked her for about two or three minutes until I came. I thought she would be disappointed, but she simply said, “That was fun” and we got dressed again. I thought about her all day and all night. I never saw her again. When I got into work the next day, I asked her friend where she was and was told she no longer worked there. Shortest first romance ever.

But that had whetted my appetite. I wanted to do that again. And I wanted to improve. I got a couple of dating apps on my phone and set up profiles for myself. I had a good body so used one of me at the gym as my profile pic. But the bio I put was complete bullshit and I think everyone saw through it. In hindsight it looked like a kid and made the profile. After about a month I had no enjoy and thought about giving up. So, I decided to ask the one person I could trust, my mom. She was very down to earth. I could talk to her about almost anything. She was happy I wasn’t a virgin anymore as she had a dislike of Michaela. Mom was not religious at all and told me I was being led down a path I didn’t want to go down. Well now I was on a path she wanted, and I needed her help.
“Be honest.” She told me. “People see through bullshit. If you’re inexperienced say you are. If you want guidance in dating, say that’s what you want.” Mom knew best. And she had dated a legion of men since dad left. I considered her an expert. So, I set about changing my profile. It took about two days for a response but then they flooded in. I my desperation, I had not set an age range on these apps and I got hundreds of likes and some messages from older women. Some really old, and some in their early thirties. A lot of married women looking for a fling. I was nineteen and seemed quite desperate, so I was easy prey. That suited me.

I picked out a couple of women who looked hot and messaged them back. They both responded. The one I liked the most had just turned thirty. She was blonde and had nice boobs. We arranged for her to pick me up after work and we went for a drive. She parked in a remote spot, and we got in the back. She made me put on a condom, and I embarrassed myself again with my lack of knowledge. There was a bit of foreplay first, but I think she got impatient and, in the end, told me to just fuck her. I lasted a bit longer. Not a great meeting but I had learnt a couple of things. When I got home, I messaged the other woman and set up a date with her. She was mid-thirties and had her own house. That’s what she told me. She lived not far away so I went over there next night. Clearly, she was married, and her husband was just not home. She was very quietly spoken, and we chatted for a while, but she kept looking at the clock. After a while, she led me upstairs to the bedroom and we got undressed. This was the first time I had seen a woman fully naked, and I liked what I saw. She took me to bed and taught me how to lick pussy. Either I was a fast learner, or she was very responsive because she soaked the bed. We did the condom thing (much better this time) and we fucked slowly. Then she asked us to change to doggy which was her favourite. That was new to me too and I quite liked it because I could hold onto her hips or grabs her tits. I know she liked it too because she orgasmed and screamed. That was a much better meet, but I didn’t feel the urge to see her again. She did message a few times, but I kept saying I was sick, and she gave up in the end.

A few days later and I was having an everyday conversation with my mom when she asked how the dating app was going. I pulled a face meaning it was okay. She interpreted it as a complete failure.
“Well, if you really are having trouble, go and see your sister, she will sort you out. And failing that, come back and talk to me again. I’ll see what I can do.” That was nice and helpful. My sister Jane was twenty-three t that stage. Still living at home but we rarely saw her. She had been through some boyfriends too so I was sure her advice would be good. From a younger girl’s point of view. I did have a few more girls’ message but only one appeared to be interested in hooking up for some fun. Her name was Lucy, and she was eighteen. Quite nerdy and shy. The others were a bit more relationshippy and not what I was looking for – at that moment. I decided that before I went anywhere with Lucy, that I would speak to Jane first. I decided that might pay dividends. Luckily for me, she was at home that night. After dinner I went to her room and told her about the apps and how it was all going. I did underplay it like I was have NO success at all.
“And mom said ‘go and see your sister she will sort you out’”
“Did she now? And what do you think that means?” I shrugged being both naive and coy at the same time. What did she think it meant? I thought help with the dating apps. She looked me up and down like I was a piece of meat.
“Show me your cock.?”
“WHAT?”
“You want me to help you out? I want to see what we are dealing with.” That made sense in a perverted way.

I dropped my pants and released my member. She looked. She turned her head to one side. Gave a slight nod of approval.
“Hmm. Okay. That’s quite nice. Come back her in an hour. And have a shower.” I had garnered the royal approval. Not sure what I was coming back for or why I had to shower. I didn’t think I was smelly. But I did what she said. I knocked politely and she called me to come in. She was sat at her vanity in a silk dressing gown. As I entered, she stood up de-robed. She was completely naked underneath. I realised why I had come back now. She had a lovely body and a nice pair of tits. Not too big but soft handfuls. I looked forward to playing with those. Her pubic area was neatly shaved. I looked forward to showing off my newly acquired pussy licking skills down there. Jane signalled that I should get undressed to. Didn’t take me long to catch her up. She walked over and knelt in from of me. This was going to be my first blowjob. She was very good at it. I’m not sure I’ve had a better one since. It was all I could do not to blow my lot in her mouth. As I neared that point, I tapped her on the shoulder.
“Your turn.” She smiled and spread herself on the bed. I never knew a pussy could smell so sweet or taste so good. I was definitely get the hang of it and managed to elicit lots of gentle moans, a few cries of ‘God, yes’ and one almighty ‘oh fuck’. Then she came. Very strongly. Hurriedly, she pushed me onto my back, sucked me for a short while and climbed on top. I lasted a good amount of time. She came again and then we switched to doggy. Her tits were perfect to hang onto and I gave them a hard squeeze as I shot my load into her.
“How did I do?” I asked as we cleaned up.
“You did excellent, little brother.” We can do that again one day. I know who to call when I’m horny.” I left feeling very pleased with myself.

It was a few more days before I saw any action. And boy, did I see it. I got home from work one day, tired and exhausted. Mom was in the kitchen talking to her sister Frankie. I said a polite hello and went straight upstairs to get a shower. The job I had was quite physical and I got quite dirty during a shift. It was nice to get clean and refreshed. When I came back down Mom and Frankie were finishing dinner.
“There’s more in the oven you’re hungry.” Mom said.
“I’m ok, at the moment. Maybe later.” I took a drink from the fridge and joined them at the table.
“Hard day.” Mom asked placing a comforting hand on my hand. I grimaced. “How’s things on the girl front?” I couldn’t believe she was brining this up in front of my aunt. I guess they were all quite open about that stuff just as we were.
“I saw Jane. She offered me a few tips. I’m chatting with a young girl, but we are taking things slow.”
“Aw. That’s nice.” Frankie said in a chirpy but patronising way. “What you really need is good womanly advice and coaching. Isn’t is Gina?” She winked and looked across to my mom.
“I offered.” She replied.
“And he declined?”
“No, I didn’t decline. It’s an option if other avenues fail.”
“Well, it sounds like they are failing now. What say we give you a few pointers?” Again, checking with mom.
“Absolutely.”

And that was how that started. No sooner was the dinner table cleared than Frankie was naked, and mom was topless. I had never looked on either of them sexually before. Mom had great breasts, that much I knew. And Frankie had a good overall figure but was a bit older. Both were mid forties and looking good for their age. I was happy to fuck Frankie. She really wanted it and had no reservations about being related. Very much like Jane was. But it was different with mom. I didn’t want our relationship to change at all. I think she felt a bit that way too. But that didn’t stop us kissing like teenagers as Frankie sucked me off against the kitchen sink. She was insatiable. Much more savage than Jane had been, but I lost a bit of sensitivity after a while, so I stopped her. She spread herself on the kitchen table legs wide open. It was a neatly trimmed pussy she had with lovely big lips. I sucked on them for a while as she rubbed her clit. She came quickly and loud. I thought the neighbours might call the police as she sounded like she was being murder. I put my dick in her and began fucking her with my hand over her mouth. I got a good rhythm and the table shook. Mom offered moral support and played with my balls. Frankie came again but more muted. I was getting closer now, so the two women got on their knees and made a cock sandwich with their mouths. No mayo but plenty of relish. Looking down into mom’s eyes sent me over the edge and I came like a fire hose. Watching them both clean me up was a delight. Frankie was pure filth and I was to discover exactly how much someway down the line. But for this day, we were done. Mom gave me a peck on the cheek, like a well done. The first chapter on my sexual experiences was done.