Mom Picks Out a Girlfriend For Me

Mom Picks Out a Girlfriend For Me

"Hey Mom?" I said, answering the knock at my bedroom door.

"How are you, dear?" My mom said as she poked her head through my door.

"I'm fine, just playing Terraria. What's up?"

"Could you come with me to the living room please?"

"Sure thing." I said, getting up out of my gaming chair and following her downstairs to the living room.

"Adam... there's no easy way to say this, so I'll just come out and say it: Dad and I are worried that you might be gay." My mom said as she sat down on our big brown couch.

I sat up in my deck chair. "What?!" I gasped. "Mom, I have no idea where you got that idea from. I'm sorry if I worried you, but I'm not gay."

My mother, as beautiful as she was, was the world's most pious Catholic. Her biggest fear was catching one of her daughters sinning in bed with a man (or worse yet- her son). The thought of her good little boy with a dick up his ass was too much to bear.

"I know," said Mom. "And we're just going to make sure that is not the case."

I sat down on the couch across from her. "And umm how is that, Mom?"

"You know Madison from down the street? The one who's parent's held that big barbecue last year for the Fourth of July?" She grinned. "Well... she has a little crush on you."

"Huh? Madison Johnson?! The one who's parents are big shot lawyers?"

"Yes that one." Mom chuckled. "I spoke with her parents and we've all agreed- you two are going to date!!!"

I shot back up from the couch. "What?! You can't just tell me who to date."

"I can.... and I am. Your father already gave his blessing."

"I'm not gay mom, I promise. I don't know why you're doing this?"

A moment of silence, then my mom responded "Honey, a boy as good looking as you, 20 years old and still has never had a girlfriend? Now I might have been born on Sunday, but I wasn't born last Sunday."

Shit, how do I explain that?! I thought. "Mom, I love you and nothing would make me happier than to have a girlfriend as cute as Maddie. But there are some things that I need to do for myself. I can't have my mom bringing women to me to date!"

"Why not?"

"It's an invasion of privacy! And I don't know... it's unmanly! What man's mother chooses who they can and can't go out with?"

"Well, so long as you live under my roof- its my way or you're sleeping under the highway."

"This is so emasculating."

"Don't worry, you'll thank me later. Besides," my mom chuckled. "It's about time you got your dick wet!"

"Mom!!"

"Oopsie! Mum's the word!"

It was decided. On Friday night I would be taking Maddie out for a date at Sapphire Wednesdays. I thought about what even to say. All these years single, I was too busy working on school and gaming, I definitely missed out on things. Other kids were getting head in the backseat during after-prom or getting drunk at parties; I was playing Yu-Gi-Oh. At college I had some friends but only a couple. Making friends, and especially meeting women, was hard. I've never gone to a party and have never even been drunk, in fact. I stayed in my room and worked on my essays. I do like women though... don't I? Just because I've never kissed one doesn't mean that I'm gay. Sure! Plenty of men haven't touched a woman until their twenties! I'm only 20, I've still got time! And as annoying as this whole setting me up on a date situation was... I couldn't deny that Madison was pretty cute. What scared me most though... was the fact I'm a virgin.

***

"Damn, look at you! Long, tan and handsome. My god, you are a serious looker!"

"Thanks mom, I just hope this goes well." I sighed.

It was true. I really did hope things went well. While I had only ever had limited interactions with Maddie- she was definitely my type. Smart, tall... a fat ass that pressed tightly against her jeans.

"Well I'm going. Wish me luck!" I said, leaving the front door in my snazzy outfit. I did not dress up often.

"Good luck hun!" My mom cheered.

I picked up Maddie down the street and together we went to the Sapphire Wednesday's by the Brendan Fraser Memorial Mall. She was dressed in an adorable little denim jacket and was wearing these long black boots. I've never seriously considered asking a woman to step on me before... but now I was tempted. I even opened up the door for her so that I could get a peek at her big round bubble butt. Luckily, it wasn't that long of a wait. When we sat down at the table we started talking and getting to know each other.

When in school, I was deathly anxious around girls my age. I never dated. Madison had not dated much either. She had only a few close girlfriends and had always been very self conscious and ashamed that she didn't have the ideal body that she saw on Instagram or heard about on the rap songs they'd play on TikTok. (She was also apparently the type to trauma dump on a first date, but hey- nobody's perfect). She was very pretty to me though. Her short blonde hair, long legs and athletic build. I'd be lying if I said I had never peeped a glimpse at her bubble butt whenever her family invited us over for holidays. Her chest wasn't exactly massive... but I didn't mind that. I'm more of an ass guy anyway. Neither of us were popular in high school but where I was playing Smash Bros with my friends, she was competing in academic challenge and in Key Club. God I hate academic clubs. Pretentious shit for people with nothing better to do, so that they can pad their resumes. After dinner I drove her home.

"I'll be honest with you, I had a really good time. I've never had such an enrapturing conversation about prevalent character tropes in Nintendo games before with a girl... well with anyone. You are really fun to talk to!"

She smiled at my compliment. "Thank you, truly. You are too, I've never felt someone listen to me as much as you have. Not just hear the words I was saying but actually listen." she said, blushing.

I didn't know what to say, so I said "Thanks, no problem. Any time." Damn my awkward tongue.

Once at her place, I opened her car door for her and carried her food to the door.

"It's so beautiful here," I said. "I can understand why you love Rowan trees."

"Yeah, they're pretty," she said. "Like you."

"Thanks I guess?" I nervously laughed. "I think you mean handsome."

"No," she said "pretty." I suppose I was kind of thin.

We starred into each other's eyes and just stood there. I was too nervous though and wimped out when I had the chance to kiss her.

"Have a good night!" I said, running back to my car.

"Thanks... you too." She said, a little bit dejected.

I felt embarrassed not kissing her. But it was probably for the best. As I drove away, I noticed her dad peering through the blinds at me.

***

"Okay," I said. "It went well." My mom had interrogated me the next morning. Prying every detail from me about the evening. "Relax. Nothing happened. We just flirted a little.'"

I could sense my mother's disappointment. "That's it?! Not even a kiss??"

"No? But there's plenty of time for that. No need to rush things."

"Son, I haven't been on a date in decades. And as a good Christian woman, I have always stayed faithful to your father- but when I was in college I at least kissed every boy I went out with. Almost always on the first date too."

There was a long pause. "Gross."

"Oh well. When you're young your passions overrun your senses. Do you know how to have sex?"

Silence.

"Oh boy. Looks like I have my work cut out for me." My mother sighed. "You see, when a man likes a woman his penis gets hard. It feels really good for things to touch it, so he'll want to stick it in a woman's wet hole that she has between her legs. This is a fun activity for married couples to do but sometimes young adults will do it before they get married. This is wrong and a sin. But... inevitable, especially for young men who are having their hormones going wild. It's not as bad, and actually somewhat ok, for a man to have sex with women before he gets married. Men have stronger urges than women."

Holy shit. I thought. My mom's really sexist?

***

Mom looked at me. "You mean your sexual endurance?"

"Yeah." I said, embarrassed. "What if I cum too soon and embarrass myself?"

"How many times a day do you masturbate?"

My face was already beet red from the embarrassing conversation, oh hell I might as well be honest. I haven't any shame left. "Once a day."

"Only once a day? For a young man like yourself? God you're only 20, you should be doing it three times a day!!!"

I looked even more embarrassed, although I wasn't sure that was even possible until now. "Well, it's hard keep interested. Usually just one is enough. I'm too busy with other things to have five orgasms in a day."

"Cheeze-Itz and rice!" my mother laughed. "Well I recommend you start doing it more often now, so that you don't embarrass yourself in front of your little girlfriend when she finally decides she can't keep it in her pants anymore. How old is she, 19? Women at that age are whores, putting everything in their pussy that they can."

I did not appreciate the way she was talking about Maddie... but was too afraid to say anything sticking up for her.

"Don't get me wrong though, Maddie seems like a nice girl sweetie. Of course they all seem like good Christian girls until they're laying on their back spreading their legs for you." my Mom said in a tone of voice that could only have been jealousy.

Mom was silent for a while. "Tell me, how big is it? Your penis. Your father's was a massive seven inches, but my brother's I saw it a couple times and it seemed to be about a pitiful five. I figure yours is pretty average then. Hardly matters I suppose, its more about how you use it than the size."

"God, Mom."

Mom grinned. "Do not use the Lord's name so nonchalantly!" She paused for a second. "Besides, you should be thanking me."

"And why is that?"

"Because I'm about to get you some alone time, so that you can deflower your cute little girlfriend." My Mom said with the biggest fucking devilish grin on her face.

***

Mom came up with a clever, yet simple, plan to get Maddie and I alone together. She invited Mr. and Mrs. Johnson over to dinner while Maddie and I were "going on a 3rd date" to discuss our future. They were after all responsible for us dating in the first place. While they'd have dinner with my parents at my house- Maddie and I would sneak over to hers. We would then be free to do as we wished. And just incase Maddie's parents left early, I would keep an eye on my phone for a heads up text from Mom. It was simple, yet effective.

***

"Mr. Johnson, please take a seat!"

"Don't mind if I do!"

"Martha! Your home is so beautiful! Is that a marble entertainment center?"

"Yes!" My mother gushed, "It's an import! From Italy! Oh yes, also dinner should be finished in about fifteen minutes! Sorry, for running a little late. It's my famous Albanian Pasta!"

"Ooooo, Albanian?" Mrs. Johnson asked.

"Yes! The noodles are a little thicker and the meat used is venison meat!"

***

Maddie and I got back to her house and immediately made a dash for the stairs with a certain giddiness to our steps. I told her about the plan and she immediately without hesitation agreed. I apologized for the fact that it was necessary, but my Dad-a work from home engineer-would never have let us fool around in my room. My mom was quite the odd one, but hey I wasn't complaining! Her love was about to get me laid!

Maddie and I sat on her bed and she smiled at me. "Honey, I... I want to. Umm well, I want to have sex with you. I've thought about it for a long time and you're just so hecking amazing and I want you. I want to be yours. And I'm willing to do anything to make that happen. I know boys are always thinking about one thing in particular, my mom told me so. And I want to give it to you- as a sign of my love."

"Woah... I... I love you too." I was a little hesitant using the L word, but I was about to have sex for the first time and didn't want to say anything that might possibly jeopardize my chances. Besides, eventually it would be true anyway. "You're an amazing woman and the only person to make me feel this way. You're kind, caring and smart with a great future ahead of you. Being a NASA engineer? That is the *coolest* possible profession I can think of for my partner to have."

"Thank you dear," she said as she got up to dim the lights. "Besides, I think you'll be very happy with what you see underneath these." She said, shaking her big ass in the yoga pants she was wearing. They were form fitting and clung intently to leave no room for the imagination. It was so sexy.

"Would you like to kiss me?" She said after taking a seat next to me on the bed.

I leaned into her body and she held me tight.

***

Mrs. Johnson said, "I knew that your son was the best candidate for our daughter, Madison. We know that... well... all young men have, or want to have, a lot of sex. We don't want our daughter to be debased when some random man that she'll only be with for a year, takes her purity away from her. We know your family well and just how devout you all are in your faith."

Mr. Johnson continued from there, "We think this is a necessary evil. And just want what's best for our daughter. Your son is always such a gentleman with us, so I know we have nothing to fear from him. In fact, your son is such a gentleman that he did not even try to impose himself by kissing our daughter after their date!"

"What are you saying?"

"We want your son to marry our daughter." The Johnsons said in unity.

"Goodness gracious," gasped Mom. "I'm not used to being the most liberal person in the house."

***

I could feel her breasts rubbing against my chest. I tried to be respectful but I could feel my dick starting to rise in my pants. I knew I shouldn't be getting these urges but I couldn't help myself. Madison looked into my face and then she kissed, sliding her tongue down my throat. We just lost control. My hands went to my new girlfriend's chest and I rubbed her orange sized tits.

Maddie began stripping. She got down to her bra and panties. Then when she unhooked her bra, her tits gently popped out. Her nipples were tiny, like dimes. They were already hard. Madison then pulled down her grey Calvin Klein panties. Her pubic hair was completely shaved off, I knew then that she had been expecting this. I got up and pulled down my pants.

Maddie walked over to and laid down on the bed. She got on her back and just laid there. I got on top of her and positioned my dick between her thighs. I pulled them apart and I moved the head of my dick into place right in front of her sopping wet pussy hole.

I took a deep breath. "Maddie... I'm still a virgin... at 20."

"Oh, well" said my girlfriend. "So am I..."

"Are you ok doing this, hun?"

"Yes." she said. "We're both adults and I'm not a prude. Please, I've been waiting for this forever!"

I didn't waste another second. I thrust my dick all the way into my girlfriend's virgin vagina. God, did she let out a painful grunt as I slid all six inches into her. There was no foreplay. I stroked as fast and hard as I could. My balls were slapping hard against my her round ass. She stretched her legs up into the air before bringing them behind my back and then locking them in place. I barely noticed as I continued to pound her virgin pussy.

She grunted. "Ah, are you enjoying your present?"

"Fuck yeah!" I said, wantonly thrusting my hips against hers.

"I love you."

"I love you too babe" I said, unconvincingly.

There was so many painful grunts at first and a little bit of blood from her hymen but eventually they turned into cries of love, as we locked eyes. I couldn't believe how tight it was! She had me in her gorilla grip as I punished her tiny pink coochie with my cock. She was a whore, my whore. Eventually, I lowered my mouth and started to lick one of her hard nipples. This pushed her over the edge.

I could feel her contracting around my cock. She just cried incoherent nonsense. We couldn't have been fucking for more than fifteen minutes. I was trying hard not to cum but I could feel it in my balls. I was so enamored by her warm, tight pussy that I didn't even bother trying to pull out. My body tensed up and I shot load after load of hot cum into her fertile sex. Maddie let out a gasp as she felt my seed hitting her vaginal walls. Her pussy clenched me tight and I dripped even more sticky cum into her cervix. I just laid there, on top oh her, for close to five blissful minutes. I then finally felt myself shrink up.

"Thank you... thank you." She said weakly.

Once we got ourselves cooled down, we cuddled for a little bit then showered together. Then later that night, it was time for round two! This time Maddie mounted me and slid down onto my cock. It was euphoric reaching up and squeezing my her cute oranges. Then she got loud. Being the selfish 20 year old I was, I put my pleasure and orgasm over hers. One thing I did find out though: Maddie HATED cum.

This time I actually did manage pull out in time and sprayed cum all over her stomach. She did not like this and was grossed out by the sticky liquid and made me grab a towel immediately. Which was fine with me, that just means next time I get to squirt my love juice into her pussy. I HATE pulling out. Eventually, though all good things must come to an end and I drove away just as her parents were about to get home. My mom, saint that she was, had talked them into watching a movie.

The next day Mom told me that the Johnsons wanted me to marry their daughter. I was a bit apprehensive at first. Until one day when Maddie sent me a long, romantic sext about how she wants my cock exclusively for herself. She wants me to knock her up after our wedding and then never stop making her pregnant. Just one baby after another. She was going to be my sex toy, and I was going to be her breeder.

From that point forward, life was awesome. I never had to beg my fiancé for sex. She never said no and loved to be of service. And because of her praise kink, all I had to do was say good girl and then sex was like Cloud Nine for her. Thanks Mom and Dad. And Mr. and Mrs. Johnson of course.