My first time with an older woman and my first time giving a creampie

In 2011 I was beginning my junior year of college. I was gaining more confidence as I made my way through young adulthood and was starting to notice more attention from women in my social circle and classes. I was in a committed relationship, but my eyes were starting to wander as I reflected on being halfway through my time in college. Hearing the gossip of my friends casual sexual encounters gave me a case of FOMO I couldn't shake. It ultimately led to me breaking off my relationship at about the six month mark. She was crushed and I felt terrible, but I knew I'd always wonder 'what if?' if I didn't have a bit of a hoe phase.

Although that would be easier said than done. I found myself too worried about ruining a friendship to get too flirty with anyone in my friend group and I didn't have enough practice picking up women at bars. Tinder wasn't a thing for another year, but I had heard about OkCupid and decided to give it a try. Honestly, I think that was the peak of online dating. I found answering the questions very fun and the match percentages were spot on. My options were somewhat limited in smaller college town, but I set a wide radius and eventually began messaging with Anna, a 97% match about an hour away. The kicker? She was 41 and I was a fairly inexperienced 22 year old.

Her pictures showed a petite frame with raven hair and pale white skin. She was in great shape for her age and reminded me a bit of Mary-Louise Parker from Weeds. I couldn't believe she responded to my first message. I told her that she was my highest match percentage within 60 miles and I just had to say hi. We chatted for a few days, very friendly but vanilla. I learned she was recently divorced and was just looking for casual fun to take her mind off of it. I was honest that I was an amateur in the world of casual dating, but open for an opportunity to change that. She seemed hesitant because of the age difference. "I'm the one pursuing you," I messaged, "I don't think you'll be taking advantage of me." That seemed to be all she needed to hear. She invited me over for a movie night that weekend.

The evening came and I started to get nervous halfway through the drive there. I'd never met someone from the internet before. What if she wasn't really getting a divorce and her husband came home and flew into a rage? What if I was being catfished? My heart was pounding as I knocked on her door. She welcomed me in with a hug and a hello. I was immediately enchanted with her voice - a British accent! I can't believe she hadn't mentioned this. She led me to the living room. She was wearing jeans and a t-shirt but looked just like her photos if not better. As we made our way down the hall, I could see the divorce wasn't a lie either. Moving boxes scattered around. Outlines on the wall where family photos once hung.

"I love the accent," I told her as we took a seat on the couch. She gave me a grin and a thank you, but I could tell it must be something she heard often in her small rural town. I asked how she ended up here and she gave me a short answer about her ex that made it clear she didn't want to talk about the past tonight.

"Have you seen American Werewolf in London? I found the DVD, I thought that might be a good date movie." I hadn't - we sat down to watch it.

The movie was uneventful, mostly watched in silence. Occasionally one of us would pipe up to comment about something on screen. When it was over we chatted about it for a bit until there was a lull in conversation. I had kind of expected her to make the first move, but we both seemed hesitant. I finally broke the silence, "I'd really like to kiss you,"

"I've been waiting for you to," she said.

I leaned in for a kiss that quickly turned into a passionate make out session. It wasn't long before she was straddling me, kissing me deeply and running her hands through my hair. I'm already rock hard and she could tell as she grinded slowly against the bulge in my denim jeans. My hands made my way under her shirt and I unhooked her bra. She stopped me. "Let's go to the bedroom."

It was a big, dark house, a little creepy. She led me up two flights of stairs to her bedroom that was almost as dark save for a small lamp on a night stand. I grabbed her waist and brought her to me again. We kissed as we made our way to the bed. She immediately begins to get undressed and I don't hesitate to follow her lead. We kiss more before she gently pushes me back on the bed and gives my cock a few strokes before wrapping her soft lips around the tip. I'm in heaven. She swirls her tongue around the tip of my cock before deep throating the length of my shaft. She cups my balls and holds her head down for a few seconds before coming up for air, leaving my cock soaked in her spit that she proceeds to use as lube, slowly stroking my shaft while placing her lips back around the tip. She was a pro.

I'm in completely ecstasy at this point. I let out several moans and a few 'holy shit'-s. She seems to enjoy the encouragement. I start to worry that I might not last long at this rate. She sits up on her knees, still slowly jerking my cock and reaches over to her night stand, pulling out a bottle of lube. She lets go of my hard cock to squeeze out some lube onto her hand and gently lowers it down between her legs. In the dim light this is the first time I notice she has a full bush - neatly trimmed but not at all shaved. This was an unusual sight for me in real life, the four other women I had been with at this point kept it completely bare, but I was mesmerized by Anna's bush. She grabs my cock and gets up to squat down on top of it. I'm so in the moment I barely snap out of it to say "I brought condoms," before she lowers herself onto me. "That's ok," she let's out in a quiet whisper.

Her pussy felt incredible. Sex without a condom was something I had done with my first serious girlfriend, but it had been over a year since we had broken up and I forgot how incredible it could be. She gently bounced up and down before relaxing into a nice grinding rhythm. I put my hand on her lower back and ease myself up, scooting back against the headboard to go in for a kiss. We passionately make out while she rides me. I have one hand cupping her ass and the other is gently massaging her breast. Anna had small tits to match her petite frame, but they were very perky, no signs of sagging with age. I break away from the kiss to and lean down to her chest, giving both her nipples a gentle lick before taking one in my mouth and slowly sucking it. She grabs a handful of hair on the back of my head, pushing my into her chest.

We continue this embrace for another minute or two before I feel my cock starting that familiar twitch. I lean in and whisper in her ear "I'm not ready to cum yet, let me taste you."

She wordlessly stopped the grind and slowly lifted herself off of me, rolling over in the bed. I roll over on top of her, kissing her cheek, then her neck, down her chest, stomach the top of her thighs before diving in. Her bush was soft and I liked the feeling against my lips. She tasted incredible and I was so hungry for her it was like I was making out with her pussy. Her thighs closed in on my cheeks, letting me know I was hitting all the right spots. Anna was quiet but breathing heavily and letting out small moans. Her legs relaxed, and I came up for a breath of air, bringing my hand up to her pretty pussy, gently caressing it with my thumb before slowly inserting two fingers and returning my tongue to her clit. She let out a breathy "Yes."

After a few minutes I'm ready to be inside of Anna again. I slowly pull my fingers away, kissing her thighs, back up her stomach and chest as I crawl towards her. We share a deep kiss. Some of the college age girls I'd been with to this point were hesitant to kiss after I'd gone down on them, but not Anna. I grab her cheeks as we kiss and I feel her hands roam my chest as I slide back inside of her. I break away from the kiss and angle her legs up to give her a fierce pounding. Beads of sweat start to form on my forehead and chest. I give her a few more passionate thrusts before letting go of her legs and leading them spread around me. She sits slightly up and reaches over towards the nightstand, pulling a small lipstick sized vibrator out of the same drawer she had grabbed the lube from earlier. "Do you mind?" she asked. "Not at all." She lowers the vibrator down and I can feel the rumble all through my shaft as I slowly thrust. This was a new experience for me and it was such a turn on.

I pick up my pace and look down to see her in the dim light, eyes rolling back, biting her lower lip. She looks so incredibly erotic and it's starting to send me over the edge. "I'm about to cum," I moan out. "Wher-" before I can even finish she responds, "inside me." This sends me over the edge and I begin to release a powerful load of cum inside of her. "Oh, YES," she lets out the loudest she's been all night. We cum together. I shoot three or four ropes into her. I'm having the most powerful orgasm I've had in my life, I can't believe how good this feels. The sensation overwhelms me and I collapse onto Anna in a sweaty mess, she embraces me with her arms around my back. We share a few gentle kisses and I slowly pull myself out, rolling over to her side.

She lays her head on my chest, "wow." I just nod. "Don't worry, I'm fixed," she says. I was so caught up in the moment I hadn't even considered that.

We stayed in a sweaty embrace until I started to doze off. She kisses me on the cheek, "Don't worry, you can stay the night," before getting up to make her way to the bathroom. I enjoy the view as she walks away.