The first time I actually met Adriana, I picked her up outside her condo building to take her to dinner. I'm a pretty confident guy but I admit I had butterflies this time. For starters, she was a 42 year old recently separated mother of two teenage girls; she had a career, owned a home and I naturally felt the pressure. Especially since I was just 22 at the time.
I had dated older women before in college but 33 was the standing record. The 20 year age gap was... something. I come from a traditional household and my feelings were like a cocktail recipe - 2 parts fantasy, 1 part confusion, 1 part taboo and a splash of primal urge. Shake well over reality and that was my mental state while I waited at the door.
Adriana came out wearing the perfect pair of jeans and a blouse donning a tasteful amount of cleavage. Considering how endowed she was, even tasteful cleavage was a mouthful in this case. Here hair was straight jet black with eyes to match and blushed through her tanned cheeks as she softly said, "Hi, Jake." Even her 3" heels were only able to bring her to about 5'5". I was a college hockey player and my athletic 6 foot frame made her look all the more petite. I led her to the car and we were on our way.
I'm not proud of it but we had originally met online. No, not Tinder or any of the other low-rent apps but a solid subscription based service that was geared towards dating as opposed to simply hooking up. So naturally my expectations were honorable. We were a couple of adults going on a first date, nothing more.
The restaurant was highly rated with a small intimate layout. We were seated by the chef himself and had drinks in our hands moments later. She was intensely pretty. Dark expressive eyes, curvy in all the right places and incredibly sweet to boot. The conversation was natural and unforced. We covered a lot of ground and got to know and like each other quite well in a short amount of time.
However, even great conversation couldn't completely get my mind off of how sexy she was. Adriana was old enough to be my mother and yet young enough to carry my children, something entirely new for me and my level of attraction for her was reaching an alarming height. But how did she feel towards me? She was clear about wanting a relationship and, while I was more than willing to give it to her, I was about to graduate from college; what could I offer a grown woman with two kids?
Still. The connection was there, all the same.
We stepped out of the restaurant and onto the sidewalk holding hands. I looked down at her big brown eyes and kissed her gently on the lips. She held me tight and kissed me back hard leaving us lip-locked on the sidewalk for what felt like five minutes. We got in the car and, before I could turn the engine over, we were making out.
"I really like you, Jake..." she said panting. Her hands were on my chest, gracefully slipping under the opening of my striped dress shirt.
"I really like you too." I replied. We made out passionately for quite a while longer. Her body felt amazing. "Where do you want to go?" I asked.
Adriana didn't immediately reply. Instead moved her hand from my stomach and over my jeans. When her hand grazed over my erection, she took a deep breath. "My kids are home," she whispered.
"Well," I thought for a moment, not wanting to suggest my lame college apartment and mood killing roommates. "What about a hotel?"
"Mmmm..." she moaned in the affirmative. After we made out for a little while longer, she asked "Are me moving too fast? I like you a lot and I don't want to spoil things..."
"I feel the same way. I don't think we should."
On the way up to our room, we held hands staring silently into our reflection on the elevator door. It was a moment to reflect on what had just happened and what was coming next. We stepped off the elevator without regret and, moments later, there we were. Alone in our room.
She sat on the bed waiting for me. Upon reaching her, she pulled me into a long, slow kiss. The next kiss was shorter and the third was shorter still. Each kiss faster and faster until we were in our underwear - me in blue boxer briefs, her in black lace. We kissed deeply one more time. "You're so sexy..." she whispered before getting on her knees and removing my cock from my underwear. Fully erect, it popped out from the tight garment dramatically. She moved closer staring longingly into my eyes. She kissed my chest lightly as her fingers ran down the bare shaft then wrapped around it as her kisses moved down to my stomach. By the time her mouth made it to my cock, her tiny hands were gently massaging my sac. I felt the warm embrace of her mouth as it took me inside. Adriana moaned quietly as she pleasured my now pulsating penis. I breathed heavily while trying not to orgasm. After nearly two minutes I, out of fear of climaxing too early, carefully moved her head off of it and bent over to kiss her.
Grabbing her by her lush ass, I lifted her up and onto the bed. Breathing hard and deep, she sat up and unclasped her bra. Her voluptuous D's said hello with two throbbing hard nipples pointed at me like a pair of pistols. I stared into her eyes and, without breaking eye contact, ran my fingers up her thigh and caressed her vagina through her saturated panties. I pulled her butt to the edge of the bed, removed the black lace off and got on my knees. Her pussy was as wet as I've ever seen. The froth was thick, rich and metallic in flavor. Her clitoris, as small as it was, was swollen and sensitive - I felt her thighs tighten around my head as my tongue parted her lips.
When I got back to my feet, it hit me like a ton of bricks.
"Shit..." I said.
"What is it??" she asked, sitting up.
"I forgot to get condoms." I said, completely embarrassed. Though, in my defense, I wasn't expecting this on the first date.
"Oh..." she replied. She kissed me deeply and pulled me back onto the bed.
"I really want to be inside you..." I said softly.
