First Time with Mom and Her Friends

This is a work of complete fiction created only by my own thoughts!

My mother had always taken my temperature rectally. Even now at 19 years old, this is what she does when I am sick. She never did it in a way that was embarrassing or degrading. And as I got older and had sexual urges, I began to enjoy it. Mom never made a big deal about me having a hard-on. My cock was nothing special - about 7" long and 2" in diameter. Circumcised.

I had come home from college for the summer and felt ill. Mom noticed I was not my usual energetic self and asked if I felt ok. I told her I felt unusually tired. She said she was going to take my temperature and went to get the thermometer.

When she came back, she sat on the couch in the study and patted her lap. I dropped my pants and proceeded to lay across her lap. She put on some exam gloves and spread my cheeks apart. Just as she was beginning to apply lubricant to my anus, the doorbell rang. She looked at her phone and saw it was her friends Susan and Courtney.

Mom told them "Come on in! We're in the study. Just come on back."

I was a bit apprehensive about this because I was not used to being naked in front of a group of women, much less with a thermometer in my ass! From the look of surprise as the ladies walked in they were not used to it either!

Susan was in her early 40's with dark hair and blue eyes. She kept herself in great shape. She has beautiful breasts - a C cup and a fabulous ass. I always like to look at her ass. I rarely ever saw panty lines, so I guessed she wore a thong. And the little crease where her upper thigh met her ass cheek was always nice to look at. When she walked, her hips had this mesmerizing sway to them.

Courtney was in her late 40's with blond hair and gentle green eyes. She was also in great shape. It was not too unusual to see her without a bra so I know her breasts sagged a little but had small hard nipples. Their shape was still great and they were smaller than Susan's, so I would guess a B cup. She had a great ass and a habit of bending over at the waist to look at things. This served to push her ass out and caused the clothing she had on to reveal her panty line. As a result, I know she wore small panties - but not thongs.

I should also tell you about my mom, Sandy. She is in her mid 40's. My dad was killed serving in the military when I was 10. Everyone says he died saving a bunch of other guys and I should be proud of him. Mom dated on and off for a while after that, but never really clicked with anyone, so she stopped. She has black hair with deep blue eyes. They are hypnotizing at times when I look at her. Her breasts are an amazing B cup - no sag at all. Amazing shape and areola just a bit larger than a quarter with small but stiff nipples. Her stomach is flat and her ass is always enjoyable to watch. She has this way of standing that just makes her whole body look so amazing. She rocks!

I did not lust after any of them, nor was I unaffected by these amazing women! They were in better shape than many of the girls in college! And they were all genuinely nice ladies! Kind, polite, caring. I have known them all my life as they have always been friends with my mom as long as I can remember.

These were the women that raised me. They all helped me grow and become who I am. So I could not deny they were hot, but I did not lust after them.

As I said, they looked quite surprised to see me laying across my mother's lap, pants down and her spreading my cheeks apart with one hand while she applied lubricant to my anus with the other. They looked at mom and she said to come in and sit down. Mom explained she was taking my temperature because I seemed a bit sick. They said they had never taken a rectal temp before. Mom asked if they would like her to show them how and realized she had not asked me.

Mom asked if I would mind being a 'teaching aid' for them and I said "OK."

They were all very pleased and mom directed Susan and Courtney to put on gloves. I could not help but to look at their asses as they turned away to get the gloves. When they turned back, I could very clearly see their hard nipples and the look of excitement in their eyes. My cock gave several strong throbs that I know my mom felt. I know she felt them because she always placed my cock between her thighs.

Mom has been putting my cock between her thighs for many years now. I don't really recall exactly when it began, but I think it began shortly after my dad was killed. At that point, it was never really sexual. Mom never did anything sexual with me. It may have been erotic, but neither of us acted on it. She seemed to enjoy it and I know it simply made me feel comfortable.

Mom would always look at my erection and say 'Looks all healthy and normal.' then call me to lay across her lap with my cock between her thighs.

At this point, Susan and Courtney were standing beside me. Mom began to explain how important it was to lubricate the anus for the thermometer to slide in easily. She got a bit of KY on her finger and then massaged my anus.

She explained to them that they should take their time and not be rushed. Let my anus relax by taking slow gentle strokes. Then, as they feel my anus relax, remove the finger, apply a little more lube to my anus and slide just the tip of the finger in. Just up to the first knuckle and move it around. Circles, in and out a bit, whatever they want. But wait again for it to relax.

Once you feel it relax, then remove it, apply a bit more lube and again insert to the first knuckle. Move it a bit more to relax me again, and then finally begin to slide your finger in and out, going deeper each time you go in and removing it to just the tip before going back in. Once her finger was buried deep in my ass, she moved it around a bit and then removed it.

A moment later the thermometer was inserted and held in for the required 3 minutes. As the thermometer was working, Susan and Courtney asked many questions about the procedure. I did not really listen as I was looking at them, thinking about their bodies, and enjoying the feeling my mom was creating. She had never done this for such a long period before. And it **excited** me a lot!

Then she asked who wanted to go first.

Susan jumped and said "Me!"

Mom asked me to get up and that is when Susan noticed my mom had my cock between her thighs. She and Courtney turned a bit red when they looked at my cock and my mom's thighs.

Mom said "Yup, it works." and we all smiled and had a little laugh.

Susan then looked at mom and said "Since Courtney and I are wearing skirts, what should we do?"

Mom looked and then said "Easy. Take them off. Then there won't be any stains."

Susan shrugged her shoulders and looked at me saying "Are you ok with that?"

I said "Not a problem for me." and smiled.

She removed her skirt and patted her lap. I laid across it and maneuvered my cock mostly into her thighs. She asked me to lift up, opened her thighs a bit, reached down and grabbed my cock to put it where she was comfortable and told me to relax again. She commented about how hot my cock felt between her thighs and then spread my cheeks apart. As she began to lubricate my anus, I noticed how slim her fingers were. And VERY long. They felt nice as she got to the part of fully inserting her fingers. She asked my mom about the bump she felt. Mom explained that was my prostate and that rubbing it would make me very sexually excited like any normal man. She rubbed it for just a few more seconds and withdrew her finger replacing it with the thermometer. Again, the 3 of them talked about things and I just enjoyed it.

Then, all too soon, it was Courtney's turn. She was very excited but hesitated a little as she started to remove her skirt. She told me that she did not have any panties on and asked if I was OK with that.

She got a very quick "no problem." from me.

As her skirt came down, I could see she was shaved. Totally. I had seen pictures of a bald pussy before but never one in real life. I looked over at Susan for a brief moment and she crossed her arms across her chest and I noted she was playing with her nipples.

Then Courtney sat down and opened her lovely thighs! She reached up and grabbed my cock right away and guided me between her thighs. As I laid forward I saw the crotch of Susan's panties were very wet. Courtney's fingers were not quite as long or slender as Susan, but felt amazing none the less. When she got to the point of inserting her finger all the way, she began to take long, deep, slow strokes in and out.

She asked me if I liked it. I said "Yessssss."

Then, looking at my mom, Courtney asked if I had ever had 2 fingers.

I said "No, can we try?"

I then felt a stretching of my ass as her second finger came in beside the first and began sliding in and out. Courtney took her time and let me relax as she went deeper with 2 fingers. At one point, I pushed back to get them in me. Courtney said "Someone is certainly enjoying this!" Both fingers brushed across my prostate. Mom reminded her to be slow and gentle. This was amazing!

I was panting a bit and Susan offered to "comfort" me. I don't recall what I said, but I soon found her nipple on my face! And I gently took it into my mouth. I caressed it with my tongue and felt it respond to me. I noted the texture as I began to suck and kiss it. After a little bit, it disappeared and I was disappointed. But it was replaced by Susan's other breast and I was happy again!

Without warning, I felt Courtney's thighs part a bit more and the warmth of a hand on my cock. It was Mom. She had stripped completely and was now massaging my cock.

This was amazing! Mom had never allowed this to become sexual at all! But man, did it ever feel amazing! Then the nipple in my mouth was pulled away as Susan stripped as well. She moved a foot stool over and sat directly in front of me with her legs spread wide open. I did not need any further direction and leaned down to lick her. Long, slow, like it would never end. I felt her hands wrap around my head and go through my hair, her fingers explored my ears, pulling me in to her.

Needless to say, I was about to cum and Courtney said she wanted to change places. Her fingers came out of my ass slowly, teasing me as they left. Courtney quickly stripped. My pants had already been removed along the way and now my shirt was also taken off. Mom told me to get on all fours in front of them. Susan moved behind me and took over fingering my ass as Courtney settled in to have her body licked. Mom continued to stroke my cock VERY slowly. After savoring her breasts and pussy, Courtney suddenly put her hand on the top of my head at the same time she pulled her legs up and curled her hips in. She was moving for me to lick her ass. Wow! Again, something I had heard about but never actually done. I went slowly and carefully. I poked and probed her with my tongue as she squealed with delight.

Then mom said she wanted her turn with me but she would be right back, she needed to get something. I was in total shock when she came back in and asked if I was game for toys. She had 5 or 6 dildoes with her and several anal plugs. I never dreamed she had so many toys. And she had what I later learned was a harness. In the harness was what looked to be a limp dildo. It was a bit thinner than my own cock but looked to be just as long. It was purple with a ball at the head. I later learned it was a jelly dildo. It had been a mind blowing experience so far and I wanted more of it.

I said "Yesssssss!"

The ladies picked toys and I was to help each of them as needed. Susan chose a long butt plug that got fat near the bottom. I licked her ass and then, with her direction, slid it in to her. I never thought she would take something this big in her ass, but it went in and she was enjoying it. Then I was asked to put a small vibrating dildo in her pussy.

Mom wanted a very long set of beads in her ass, each bead was larger than the previous one. I never thought mom was so kinky. I had a lot to learn about her. Then she wanted a long thin dildo in her pussy with a big egg shaped head on the end. I licked her a bit and slid it in. It also vibrated and she set it where she liked it. I could hear it vibrate.

At that point, Courtney said she wanted to go first with the strapon. The harness had a place for a butt plug and she chose a rippled plug. I licked her ass and slide it in oh so very slowly. Then a short but fat dildo for her pussy before putting on the harness. By this time, I had spent so much time with multiple fingers up my ass that I was not worried about the strapon but instead I was very excited. Mom came over and nestled in front of me, spreading her legs wide open revealing wetness running down them. The little vibrator was still in her and she pulled my face to her pussy. I moved forward and began a series of long slow licks as I felt her vibrator inside of her.

Susan moved to my side but slid under me, taking my cock in her hand and giving me a lick on the head. Then I felt Courtney come up behind me and put one hand on my hip as the other hand guided the head of the strapon to my anus. She had already applied lube to it and slowly began to tease my ass with it.

I looked up at mom. Her eyes were indescribable. They looked a bit glazed over. Her hands were on the side of my face pulling me in and guiding me. I slowly began licking up the center of her slit with each lick going just a tiny bit deeper. The vibrator was going strong. As I did this, Courtney began to slide the strapon into me. The head spread me wide open, almost feeling too big. Courtney put it in and all the back out several times. Then she finally let the head slide all the way into my anus. Once she was in, she began with slow but long and deep strokes. Then her speed increased slowly, but getting faster all the time.

Susan reached up and felt around my ass while the dildo was sliding in and out. So much sensory input! It all felt just amazing - smells, tastes, sensations of wet, full, friction, fingers on me, women moaning and just the lust of the group of us.

I decided to reach back with my tongue and try to please mom's ass. Even though the beads were there, I managed to make her squeal. Then she said I should play with the beads as I licked her ass. As I did this I felt Susan's mouth engulf my cock. It was so amazingly warm and soft.

I knew I was going to lose it quickly and I removed my mouth from mom's ass just long enough to say "CUMMMING..."

Courtney pressed as deep in my ass as she could get, Susan also sucked my cock as deep in her mouth as she could and mom pulled my face deep into her ass and begged me to pull out the beads at the same time! I began pulling them out slowly - letting them stretch her anus open as each one came out. It took a lot of concentration from me, but I wanted to make her cum.

Then I could take it no longer...

It seemed like I shot cum forever...

Susan swallowed it all. Mom convulsed in my face and I could feel Courtney shiver in my ass. It was totally over the top amazing!!

After we all came back down, mom explained that she had never let it become sexual before, but she really enjoyed it. Susan, Courtney and I all agreed it was terrific. Then the ladies looked down at my cock and saw I was still hard. They smiled at each other and asked if I was game for more play time.

I smiled and said "Hell yes!"

I will say looking back on it, it was so amazing to be able to learn about sex in an open environment with experienced women. I only dated girls my age a few times before I realized that they did not have enough sexual experience for me. And then I only dated women. Who knew and understood about sex. My couplings with mom, Susan and Courtney continued for many years and up to today. Thank you ladies. You have made my life totally amazing!

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Thank you all for taking the time to read my story. I hope you enjoyed it. Feedback is very much welcome. This is my first story.