Measuring my cum Pt. 14 by aspenfox

“I’m really not sure Jacob,” she had said, “About you seeing all these women yet. They all sound very experienced and you’re not. Maybe we should wait a bit longer and see how we can get along between the doctor and us, and maybe your aunt Jean might agree to help.”

I didn’t have a problem with that, and in my easy going way I just nodded and said “Ok, mom.” I was no fool and knew I was onto a good thing here, getting mom’s pussy and ass as I wanted. Anything else was just a bonus!

Mom & I continued our fucking session regularly over the next few days, and I just couldn’t get enough of her glorious full backside which she let me fondle and play with to my heart’s delight anytime I wanted!

One evening not long after we had read the doctor’s note, she said “I’ll ring Dr Taylor and see if we get another session with her as it was such a turn on for us both last time. Let’s get her thinking she will introduce us to intercourse.” I liked the way mom used the word ‘intercourse’ instead of ‘fucking’.

After returning from college the next day, mom described the conversation she had with the doctor on the phone.

Dr Taylor had been quite pleased to hear that mom was willing to ‘take things further,’ which of course, meant mom was agreeable to the doctors suggestion to let me penetrate mom as part of my treatment. The doctor obviously did not know we were already well past that.

“When we see the doctor, you must play completely innocent, Jacob,” mom said, as she broke off re-telling of her phone conversation with the doctor. I nodded my head.

Mom continued, “Dr Taylor also asked me if I owned any suitable underwear, and to bring it along at the session, as she thought it may help in stimulating you.” I smiled hearing this. “Of course I knew what the she meant,” continued mom, “But I played a little innocent saying ‘you mean something sexy?'”

“Yes”, replied the doctor.

“I’ll see what I can do — would black stockings, bra and panties do?”

“That sounds just fine Marge,” said the doctor. They then confirmed the time and both said they would look forward to seeing each other and hung up.

The session had been set for the next day at 4.30 pm. Mom said she would leave work a little early, go home to shower and change and then pick me up from college at 4 o’clock.

Hearing mom describe the call with the doctor had an immediate effect on me, and my cock was soon buried inside mom’s eager and willing pussy as she bent over the kitchen table. Without much ceremony, I had lifted her skirt and yanked her panties to one side before burying my cock deep in her. I thrust in and out as she slapped her big fleshy butt back against my balls and groin. I swore as we fucked and called her a dirty bitch, amongst other things. It was an enjoyable part of our fucking now, swearing and using dirty language, which she liked and encouraged me to use, and she responded in turn, which spurred me on further, until I spurted inside her.

During the next day at college I had a semi hard on thinking about what we might all end up doing in the doctor’s office later in the afternoon.

Mom picked me up on the dot at four. She looked nice with her hair done and make up. She was wearing a business suit with a skirt that was just below knee length. She looked like she’d come from work, but I knew she had been home first. I kissed her on the cheek as I fastened my seatbelt. As we drove off, I let my hand wander down over her thigh and under the hem of her skirt to her stockings over her knee. I stroked my hand upwards over the silky material, exposing the tops of her stockings and naked thigh, and briefly stroked the exposed skin there.

“Now, now tiger,” mom said, smiling, without taking her eyes off the road. “Be patient, you’ll see a lot more of me very soon. Just make sure you’re nice and hard for momma,” and she licked her lips, letting her tongue linger outside them momentarily.

Fuck, what a tease! I was hard in my pants. I chuckled in response and looked at the road in front, hitting the window wind-down button on my door side as I did so. The wind blew back my hair and cooled down my face and lust, somewhat. I was looking forward to the rest of the afternoon and evening.

We were let in by the same mid-thirties looking blonde as last time. She welcomed us with a smile and ushered us in. She wore a tight fitting white nurse type outfit, which had quite a low cut top. The tops of her tits were clearly visible like last time, and my dick responded with a twitch at seeing them again. I followed directly behind her as she walked in front of mom and I, watching her ass sway sexily. Fuck, she was hot! There were no other patients in the waiting room, and the receptionist led us straight to the doctors consulting room, knocking loudly on the door as she did so.

Dr Taylor stood up from behind her desk and welcomed us with a broad smile. She told the receptionist, whose name was Cynthia, she could go home early, just like last time.

The doctor wore a white coat, but it was unbuttoned at the front, and I noticed she was wearing a black skirt and dark brown v-neck sweater underneath which showed off an ample cleavage.

“Marge, Jacob, how very good to see you again,” she said beaming at both of us.

Mom and I reciprocated with smiles that contained an edge of cheekiness, as we were about to lead the good doctor on with some pretence in connection with our sexual activities so far.

The doctor led us straight into her inner consulting area and I looked around remembering it as before – it had a much more cosy and informal feel to it compared to the doctor’s main consulting room. It was more homely and even intimate. There were matching lampshades, a luxurious beige carpet with a large roomy black leather sofa and a separate matching sofa chair. At one end of the room a very comfortable looking milky chocolate coloured leather bound couch/examination table was placed in the centre space so you could walk around it, where I guessed people could lie down. There was also a door to another room, which I remembered was the rather nice shower/bathroom.

“I have no other patients today, so we can relax and take our time,” said Dr Taylor. “Please do sit down.”

Mom and I sat down next to each other on the large black leather sofa.

“May I offer you a glass of red wine?” said Dr Taylor moving towards a drinks cabinet. “I often have a glass after work to relax.”

Mom and I both said, “Yes,” almost in unison.

The doctor brought over two full glasses and placed them on the low coffee table in front of the sofa.

She then took a glass for herself and sat down opposite us. She had removed her white coat before returning to the sofa.

She crossed her legs, showing us her black stockings and low-heeled shoes.

“So how have you been getting on since we last met?” asked Dr Taylor keenly.

Mom answered first, “Well we’ve been collecting samples as before, but I’ve had a think about what you said last time, and I think I’m ready to go to the next stage of the treatment you recommended doctor.”

“Good,” replied Dr Taylor. “I take it you are both agreeable to penetration, for medical reasons, of course?” she asked directly.

Mom and I both nodded.

“It is rather unusual doctor, and I do feel little awkward about it,” mom added, “But if, as you say, it is required to resolve the problem Jacob has, then I am willing to act as a ‘body donor’ so to speak. I am a little hesitant, but I hope you will be able to help us perform the act so we are both able to deal with it in an adult way.” Mom spoke very convincingly, although it was a pretence.

“Yes, of course,” replied Dr Taylor. “I do understand your hesitancy, Marge. But do take it from me that penetrative sex is what Jacob requires in order to balance the bacteria present in his body, and it will lead him to be completely normal in due course. This whole matter will remain entirely confidential between us, so you need not worry in that sense, as no one else will know.”

“Oh, that is a relief,” replied mom, continuing her ‘act’.

“And what did you think of the note I gave you last time?” continued the doctor. “I believe, I mentioned Jacob would benefit from mixing of his genital fluids with a wide range of women, such as the ones I suggested, who are clients of mine and also very discreet.”

“Well, doctor, replied mom hesitatingly, “I did think it over, and for now I’m not so comfortable with him seeing anyone else. Perhaps in a few weeks, but I just can’t bear the idea of him going with some strange women yet.”

“I see,” said Dr Taylor, looking slightly disappointed. “I do understand.”

“But,” continued mom, I do have a sister, Jean, who I may be able to persuade to help us.”

The doctor’s eyes lit up momentarily. “Oh yes?” replied the doctor, “Do tell me more about Jean.”

“Well Jean is now a widow and lives on the west coast. She is a couple of years younger than me and I may be able to persuade her to help us, perhaps with some support from you. My sister is a very straightforward lady, who might like to help if the recommendations came from someone in authority and held in professional esteem, such as yourself.

“I see,” said Dr Taylor. “Well I’m sure I could give you a letter to send her, explaining the medical reasoning of the treatment required for Jacob, or perhaps you could, bring her to see me, whichever suits you best.

“Thank you doctor. I will let you know,” replied mom with a smile.

All three of us had been taking sips of the wine as we sat and talked and I was feeling quite relaxed due to it. I was sure it was having a similar effect on Dr Taylor and mom.

“Jacob, you’ve been a bit quiet, so far,” said Dr Taylor.

I smiled a response “Oh just happy to listen,” I said. “I’m just pleased everyone is so keen to help me,” I added truthfully.

The doctor beamed a smile back at me.

“Well, now,” she replied, “Perhaps we should make a start. The purpose of this session is to help you and your mom to begin the process of penetrative sex so that by allowing the genital fluids to mix, your medical condition is treated. I hope that by helping you both to break the ‘barrier’ so to speak, here in my presence, you will be able to continue the treatment at home. Is that understood?”

Mom and I both nodded in agreement.

“Whatever I suggest you do,” continued the doctor, “Please try to act as naturally as possible during the sex act and leading up to it. I am also going to suggest some foreplay so as it get you both best aroused, and as the facilitator to the treatment, I will give you instructions and may participate to a certain degree. Are you both happy to follow my instructions and for me to participate in the treatment as I see fit? This may involve certain mutual touching and verbal encouragement, which normally occurs during sex.”

“Yes, that will be fine,” said mom

I nodded, and felt my dick twitching in anticipation.

“Also, I think it would be appropriate to use normal everyday words which men and women use for our body parts and the act of sex, which may be considered rude in the wrong context, but for our purposes the context is entirely appropriate and suitable. Are you both happy with this?”

Again, mom and I both nodded. This sounded like it couldn’t get any better!

“Good. I am so pleased we are all happy with this arrangement, which you must remember is purely for medical reasons,” said the good doctor.

“Now, Jacob, I want you to go into the bathroom, take a quick shower and then come out wearing the white bathrobe I’ve left in there for you. There are plenty of towels, so just help yourself.”

I remembered how clean the doctor liked everything to be, so I happily got up to, oblige, leaving mom and the doctor to continue drinking their wine and I assume, decide what would happen when I emerged from the bathroom!

Entering the bathroom, I noticed how luxurious it was. There were very fancy looking tiles on the floor and walls, a walk in shower with multiple shower jets and curved clear glass sides which looked big enough for at least 3 people, a large jacuzzi style bath as well as a toilet and bidet. There were plenty of fresh white towels on a warmed towel rail and a couple of white bathrobes made of towelling fabric hanging on two hooks behind the door. This was certainly not the type of bathroom I expected to find in a doctors surgery, but it was great nonetheless!

I took my clothes off and placed them neatly on a cabinet, and entered the walk in shower. The multiple power shower sprays hit my body from different angles, and were intense and invigorating, and I cleaned myself all over in no time, paying special attention to my dick, balls and ass crack.

I towelled myself down. My dick was feeling a little ‘filled’ in anticipation, making it look longer whilst hanging down, but is wasn’t quite erect. I gave it a quick feel and stroke to try and relax it, and then pulled on the white bathrobe.

As I entered the inner consulting room again, was met with a most delicious sight. Both ladies had their backs to me, and turned around as they heard me come into the room, but not before I had a chance to look at them momentarily ‘from the rear’, so to speak

Mom had taken off her clothes and was wearing just a black half cup lacy bra with her boobs almost hanging out, black mid-sized lacy panties which clanged to and emphasised her large butt wonderfully, black stockings and black stilettos. Fuck she looked hot!

The doctor too had taken off her clothes and was also in black bra, panties and stockings, although not quite as sexy as mom’s. This was the first look I had of the doctor without any clothes and although she was much stockier in build than mom and so a bit less shapely, her large ample boobs looked gloriously suckable, and her big wide panty-wrapped butt looked enticing.

“Wow, you guys look good,” I said, as I entered the room.

“Thank you dear,” said mom. “The doctor had suggested I try to dress up suitably to try to stimulate you, and I think the wine has taken away my shyness.”

“I also thought it best to try to contribute and help the stimulation,” said Dr Taylor smiling, and I know you like ‘bottoms’ from what your mother has told me, so I did not think it amiss to go down to my underwear as part of this session.

“That’s fine doctor,” I said, “I do appreciate your attention to detail towards my needs.”

“Now,” said the doctor, I would like to try the first penetration, in a position such that you do not need to look at each other, which may make it easier to perform – the doggie position. Marge I would like you to kneel on the sofa with your hands holding the top edge of the sofa, and your bottom sticking outwards toward the coffee table. I think this will also help get Jacob stimulated and hard.

Mom walked over to the three-seater leather sofa and positioned herself as instructed. Fuck she looked damned hot with her white skin contrasting the black lingerie and black leather in the background!

The doctor dragged the coffee table out of the way and walked me over so I stood a couple of feet behind mom’s ass which was sticking out towards the edge of the sofa seat with the doctor standing next to me.

“How do you like the sight of your mom’s ass in that position Jacob?” said Dr Taylor.

“It looks very arousing,” I said. My dick was tenting up my robe at the front.

“Are you comfortable Marge” continued the doctor.

“Yes, very,” replied mom.

The doctor undid the belt on my robe so the front fell open and my dick shot out semi hard.

“Ah good,” said the doctor. “I see you are stimulated.” The doctor wrapped one hand around my shaft and started wanking my dick to get it harder. Then after a minute or so of doing this she pulled off my bathrobe completely, and threw it on into one corner, leaving me totally naked. My dick was semi erect with mom still positioned doggie fashion on the sofa a couple of feet in front of me.

“That’s better,” said the doctor. “Now you can proceed more naturally.” She looked quite pleased at my nakedness, and I was secretly getting quite a kick out of being like that in front of her, with mom so sexily positioned just a few feet away.

The doctor then with her right hand gave my balls a brief cup and squeeze and started to pump my dick again, and with her left hand she started to caress and grope my ass cheeks. Fuck! It looked like she was getting some pleasure out of feeling me up now! I realised mom had been right in suggesting the good doctor was a lot more ‘hands on’ than we had originally thought!

After another minute or so of the doctor feeling up my dick, balls and ass, she said, “Now Jacob, I am going remove your mother’s panties and you may play with her ass a little.”

The doctor moved over to mom and slipped off her black lacy panties, sliding them down her hips, knees and legs and then off over her feet, as mom positioned herself to ease the process.

I now had mom’s beautiful large, fleshy ass cheeks in front of me. I had seen them like this before of course, but the doctor did not know this, as the whole aim of this session was to get the doctor thinking she was the one to introduce us to fucking proper, and join in with us.

“Go on, play with your mom’s ass cheeks,” said the doctor encouragingly.

I moved so I stood directly behind mom’s ass as she knelt, with my dick still half erect and gave mom’s ass a good grope and feel.

“Does that feel nice?” asked Dr Taylor.

“Oh yes doctor,” I replied. “It feels fabulous.”

“And you Marge, do you like it?”

“Well, yes, I guess so. It does feel rather nice, although a little strange knowing Jacob is doing it,” said mom, play-acting a bit.”

“You’ll get used to it and more,” replied the doctor. “Now Jacob, I want you to kneel down and kiss and lick your mom’s ass as I pull open her butt cheeks.”

The doctor stood next to mom, slightly to one side, and gently prized open mom’s fleshy ass cheeks so that I could see her pussy and asshole clearly.

Needing no more encouragement, I knelt down as instructed and kissed the fleshy part of moms ass cheeks the doctor hands were not on.

“Lick mom’s pussy as well,” instructed the doctor. “It is all part of the foreplay.”

I lapped at mom’s pussy for a while licking her labia lips and the pink flesh inside her cunt.

“Now, lick your mom’s asshole.”

Fuck, this doctor was hot and dirty! My dick was now rock hard as I moved my tongue around mom’s rosebud. This was one of my favourite things to do with mom! I just loved rimming! I let my tongue go deeper into mom’s asshole as she squirmed in delight as I did so. The whole thing was incredibly hot and horny, especially as Dr Taylor held open mom’s ass cheeks as wide as she could with her hands and encouraged me.

“Now lick from asshole to pussy and then pussy to asshole, and back again.”

Fuck!

I did as instructed as I darted my tongue in and out of mom’s asshole and then down to her pussy, darting it in and out and licking around, and then back to her asshole again, and then in reverse.

My dick was now raging hard and pulsating up and down.

The doctor must have sensed or seen this as she then said, “Now, Jacob, ease your prick into mom’s pussy.”

I stood up and adjusted myself to the right height by bending my knees slightly.

The good doctor still held mom’s ass cheeks open for me with her hands as I brought my cock head to the opening of her cunt.

I plunged in, in one stroke I was so desperate. Mom gasped. The doctor said, “Steady now son, not too fast.” I pulled back letting mom’s muscular pussy walls claim their grip on my dick. Then I thrust in again and pushed forward.

That’s right Jacob. In and out, not too fast and not too slow, just do what comes naturally,” continued the doctor encouragingly.

I continued pistoning mom’s cunt and it felt glorious. The doctor let go of holding mom’s ass cheeks open as I was now well and truly in and she instead kept one hand on my ass as I thrust forwards and backwards. It kind of felt strange and nice at the same time!

The idea that I was now fucking mom in front of the doctor was really turning me on, and I was sure mom was feeling the same, although she did not let on. Her face was buried in the top edge of the sofa and her arms were partly over the sides of her face so we could not see her expression, but she let out some groans of pleasure as I continued to pump her.

“That’s right Jacob, fuck your mom, stick your hard dirty cock into her juicy cunt and let all those lovely juices mix and make you better,” uttered the doctor.

I continued my thrusts and then noticed the doctor had removed her hand from feeling my ass as I pumped and saw she was unclasping her bra. Fuck!

As her bra came off, I saw the doctor’s large pendulous boobs from the corner of my eye as she stood next to me, and again started pushing and feeling my ass cheeks as I thrust into mom.

The doctor’s tits wobbled and jiggled roughly and I noticed two large pinky-brown areoles and nipples, as I looked sideways momentarily.

“Go on fuck her hard Jacob and watch my titties at the same time.” Fuck this was amazing.

The doctors tits and dirty encouraging words were fuel o my raging fire of lust now, and I increased the pace of my thrusts and even slapped month ass cheeks a few times as I gripped her love handles.

Then, incredibly the doctor left my side and shot around to the back of the sofa so she was now facing me, and placed her hands on the top of the sofa near where mom’s hands were. She then bent forward ever so slightly and started moving herself from side to side so that her tit’s hung down and wobbled and jiggled sideways as she did so. Mom’s head was still buried in the sofa so she could not see this, but it was an incredible sight!

As I continued pumping mom, the sight of Dr Taylor’s pendulous, melon like boobs jiggling and wobbling and hanging down almost like udders as she swung them, pushed me over the edge.

I knew I would not last much longer now as and after just a few more thrusts I blew my load deep into mom’s pussy with a loud “Ahhhhhh…..,” as I did so, followed by several grunts as I spewed inside her, each groan timing with a spurt of my cum.

Mom also groaned loudly as I came, indicating she must have at least orgasmed too.

I became light-headed and I closed my eyes, still holding onto mom’s hips as the last of my cum waves eased and my dick became limp. Fuck, that had felt so good…..”