by Janet

Gender: Female
Age: 42
Race/ethnicity: White
Current location: Kentucky
Highest education received: Some college (not currently in college)
Occupation: Secretary
Relationship status: Divorced
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Fooled around with a girl friend
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? None

Really Big Surprise

How long ago did this hookup happen? 6 months ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling, fuck buddies

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? J is 25 years old 6′ tall, 180 lbs athletic build. Brown hair blue eyes and a neatly trimmed beard. He moved back to our home town after 5 years. I’m 5’4″ petite 105 lbs (measurements 32B-24-34) with my ass and legs as my best feature. I was looking for someone younger to have a good time with. I met him when he came into my office to pay his water bill.  It started out with small talk and his phone number then lead to something much bigger.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We decided to go out to a bar in the next town. I was 20 years older than him and felt nervous that I was too old. We had a few drinks and danced the whole night. As the night went on we both became very touchy feely with each other. I wore a small white and blue summer dress that showed off my legs and butt. He had a country style button up shirt with a pair of jeans that showed off his cute butt. By 11pm we couldn’t keep our hands off each other. He had his hand in my panties fingering my wet pussy, and I had my hand on the big bulge in his pants.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We ended up in his truck leaving the bar. We end up in a near by hotel with a jacuzzi tub. He started undressing me down to my white g string. Kissing me while cupping my breast and teasing my hard nipples. He had taken off his shirt to reveal a tone fit chest and abs. I make my way down to his belt as I’m opening his jeans up he stops me. With a big smile on his face he pulls out the most massive dick I have ever seen. I was shocked, amazed and alitte scared all at once. With my hand over my mouth and a shocked look I reached out and grasped the middle shaft. My hand and fingers could not encircle his thickness. His length surpassed my forearm from elbow to wrist. I started stroking his now fully erected dick with both hands while sucking the head of his dick. After a few minutes he lead me over to the bed and laid me down at the end and planted his face between my legs. I felt his finger explore my pussy as he sucked and teased my clit. Orgasm after orgasm shuttered through my body as my legs started shaking and a flood poured from my little pussy. He then took a quick break from my pussy to ask if I wanted him to use a condom. I told him I had some in my purse. He leaves me helpless naked laying in a pool of my juices. He comes back and is having trouble putting on a condom on his monster. After fitting it over his huge mushroom head he laid me on my back and started rubbing his dick around my pussy lips. Using my juices along with a bit of Ky jelly to lube his massive dick. I remember looking down and wondering how he was going to fit that monster in my little pussy. He was surprisingly gentle and slow. I felt my pussy spread and streach around his thickness. He pushed and pulled his dick in and out taking short slow strokes. As I became more accustomed to his size he began to go deeper and faster. Finally he bottomed out, and I let him know he reached the end of my pussy, further than anyone or anything had ever gone. I reached down to realize he still had  4″ that would not fit. He started pumping me into a orgasm. After several minutes of getting use to his size he pulled out to find the condom has broken. I told not to worry about a condom I was on the pill. He turned me around and mounted me doggy style but this time he was not as gentle. Pumping my pussy as I’m screaming with delight. I lost count of the number of orgasms. With every stroke I could feel my clit rub against his dick adding to each orgasm. I then stopped him and made him lay on his back. His dick stood straight up like a tower. I gave him a kiss on the tip of his dick and climbed to the top and settled my worn pussy down as far as I could go on his dick. Several inches still lay unattended as I started riding up and down. I had to lean up near his stomach to keep from his dick going too far. He soon took charge picked me up and laied me on the bed never taking his dick out while he pumped me in to the most intense orgasm I had ever had. He pulled his dick out and laied it on my stomach. I felt his balls against my pussy lips and his head lay past my bellybutton under my breast. He started stroking with both hands as I feel his balls contract against my labia as he came on my breast, stomach and neck. We collapse on each other and lay down reflecting on the past hour. We later wash each other off in the jacuzzi tub and end up having a quicky the next morning.

Did you have an orgasm? Did your partner(s)? We both had orgasms, me more than him.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We tried using a regular condom, he is too thick for regular condoms. Later we tried magnum xl, theyfit and mysize brand when having sex with multiple people.

What were your REASONS for having this hookup? Looking for someone who is up for sex at a moment notice.

Were alcohol or drugs involved? If so, how much? Alcohol

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We became close friends, and fuck buddies. He and I have explored our sexuality with others. I have experience and opened up to female sex partners with J. He has become more open to mmf sex, rather than mff or mf sex.

To whom did you talk about the hookup? How did they react? My friends know and some have joined us in sex. Most don’t believe his size so I have a pic on my phone or I have had him show in them in person. First person to know was my best friend Tammy. She and I had experimented before now I have both a guy and a girl who share my sexual experiences together.

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? No it opened my life to new things.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best was how I haven opened up to new exciting experiences, and j can’t think of a worst. I look at myself different in a sexual way. I have changed my way of life.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? Having a huge dick isn’t everything. J introduced me to a way of life by showing me that I’m not constricted to sex on a one on one bases. I feel free since our first encounter.

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