This past weekend, I took a 4-day, 3-night roadtrip with my girlfriend, Heather, and her 18-year-old daughter, Ava. Heather and I have been together about 2 years and how we met is probably worth its own story, but the important background is that this is the first time I would spend any significant time with Ava.
To set the scene, Heather is a hot 39 year old blonde. I'd call her a MILF since she's had 3 kids but you wouldn't know it by looking at her. She's 5'8" and has been mistaken for Ava's older sister multiple times. She's got a nice ass and the most perfect natural 34B breasts I've ever seen. Her nipples are constantly hard and, anytime she goes out without a bra (which is often), they will clearly show through her top.
I didn't give Ava's looks any thought until recently. She has a nerdy alternative aesthetic, with dark hair, glasses, piercings, and a couple of tattoos that she has gotten in the last few months. Honestly, she's not really my type as I typically go for hot blondes (hence Heather).
Recently, I wouldn't exactly say Ava's "blossomed", but she has been dressing less conservatively and showing off her assets including her perky 32C breasts. She's a 5'9" volleyball player and is fit, which means her ass is damn near perfect. I remember when I noticed it just last month...it was the first time I had seen her in leggings and my jaw almost fell to the floor I was so shocked.
Our roadtrip was celebrating the teen's recent graduation from high school. Ava and I didn't know each other very well before the trip, but we were friendly. There was maybe even a little bit of light flirting from her side.
Before we went on the trip, I had questions for Heather about how this was all going to work out.
"Ok, what am I going to wear to bed?" This was probably the 6th logistics question I asked Heather about a week before we picked up Ava.
She sighed. "What's wrong with what you have on now?"
I looked down and thought about if I had any problems lounging around in a soft, black cotton t-shirt and black boxer briefs.
"Don't you think Ava might be uncomfortable seeing me in my underwear?"
"You and Ava are basically family at this point. She thinks of you like a step-dad." She put her hand on my face, and smiled. "Just don't overthink it". And I tried not to.
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On the roadtrip we requested rooms with 2 queen beds each night, Heather and I in one bed and Ava in the other. I thought Ava might be pretty shy sharing a room with me, but it went as well as I could have hoped for. She didn't even react when I came out of the bathroom in my boxer briefs, even though I couldn't help but wonder if my bulge was too obscene.
~~Thursday: Night 1~~
The first night, Ava changed in the bathroom and came out in her "pajamas". I put pajamas in quotes because all she wore was a pair of her boyfriend's boxer briefs (damn, what an ass!) and what I think most would call a "cami". The cami was black, silky, and with a bit of lace over her cleavage. Cute, bordering on sexy, but not overtly.
Heather had let me know ahead of time that we wouldn't be having sex on the trip and I completely understood that she didn't want to risk getting caught and making her daughter uncomfortable. I for one was just loving life sharing a room with 2 objectively beautiful women: eye candy galore!
We settled into our beds: Heather and I in one and Ava in the other. I spooned Heather and it didn't take long for me to start to get hard. Again, I wasn't expecting anything, it just happens when I'm holding her and feeling her soft skin. After a few minutes, Heather reached back and was lightly stroking my cock through my underwear and I was quickly fully erect. The idea of doing any type of fooling around while Ava lay just a few feet away entered my mind and would not go away.
Since I wanted to respect Heather's wishes, I wasn't going to make any moves, but she took care of that for me. She slipped her hand into my boxer briefs and started stroking me. At this point, there was no turning back. I gently caressed her breasts and felt her nipples get even harder under her thin nightgown.
I was ready to see how far Heather would go. I placed the elastic of my underwear under my balls to be more unencumbered. I'm sure many of you know the move. Heather continued to keep me hard with her hand, but at this point, I didn't need any help. I lifted her nightgown and slowly, to keep the noise to a minimum and to give Heather a chance to stop me if she wanted to, placed the tip of my cock at the entrance to her pussy.
The light from the bathroom was on and I could see that Ava had her back to us. There was very little movement, just her steady breathing, but I still kept my eyes on her as I ever so slowly entered Heather. Heather's breath was getting ragged as I filled her up and paused, enjoying the sensation.
I had never had sex with someone else in the room before and the fact that the 18-year old daughter of my girlfriend was so close was unlocking a kink I didn't know I had. Could she hear us? I was pumping slowly in and out of Heather and we were being as close to silent as we could be, but the thought that she might know what was happening was turning me on.
Fueled by the scenario, it didn't take me long to reach the point of no return and I got close to Heather's ear to let her know. She nodded. I looked back at Ava as I started to come, unable to contain a quiet grunt. Heather let out a small gasp herself, but Ava remained still as I emptied myself into her mom. Leaving my cock to soften inside Heather's warmth, we both relaxed and drifted off to sleep.
~~Friday: Night 2~~
On the second night, Friday, Ava left one of her bags that had her boyfriend's boxer briefs in the car. I offered her one of mine so that she didn't have to run out and she surprisingly accepted. I conveniently forgot to mention that I had comfortable athletic shorts she could sleep in and was glad I did because I was definitely enjoying the view of her volleyball player's ass stretching the fabric of my boxer briefs.
Like the first night, the three of us went to bed at the same time. This time Ava wearing a top that was a bit more risque. It was a similar style with lace at the top, but instead of covering her stomach, it ended just below her breasts. I quickly got into bed when I saw what she was wearing as I knew looking at and thinking about Ava's flat stomach would leave me hard.
I had been thinking about the previous night and was hoping Heather was up for some more fun tonight. Earlier in the day when we had a moment alone, Heather had smirked and said "That was hot" when I asked her what she thought of the previous night. I felt comfortable to once again spoon her and this time I was already hard, partially thanks to thoughts of Ava's body. After a few minutes, Heather reached back and, in a replay from Thursday, stroked my cock.
I lifted my head from the pillow and looked towards Ava. I could see in the dim light that this time she was facing us, but it seemed like she was already asleep. I once again took my cock out and entered Heather while looking at her daughter.
I wasn't as careful and slow this time and Heather moaned softly. Honestly, I didn't want to be as careful and a part of me, maybe even a large part, wanted Ava to see me fucking her mom. I was also horny as fuck and I lifted one of Heather's legs so I could pound her more easily.
I still wasn't satisfied though and I decided to press my luck. I withdrew my cock and pushed Heather onto her back. While still mostly under the covers, I got on top. Heather hissed "Nooo", but she was smiling as she said it. I sank into her again and she felt even wetter than before.
Thursday, even if Ava was awake, it would have been difficult to see what was going on. This time, it looked and sounded like two people having sex. Quiet sex, but sex nonetheless. I looked over and Ava was still facing us. I couldn't tell whether she had her eyes opened, but I imagined she did and that she was touching herself. With that thought in mind, I quickly came, grunting more loudly than Thursday.
~~Saturday: Night 3~~
On the third and final night, Saturday, Ava was in the bathroom getting ready for bed. Heather had clothes strewn on our bed, so after my shower, I laid down in the middle of Ava's bed on top of the covers and played around on my phone. Soon, Ava came out of the bathroom wearing another pair of boxer briefs I had given her. I had been anxious to see her top and was a bit disappointed when I noticed it covered more than each of the previous two. It was a thin, white, thin, short sleeve shirt.
As Heather replaced Ava in the bathroom to shower, Ava came to her bed (which I was laying on) and fiddled with items in her toiletry bag. She was standing there for about a minute before I looked over. She was bent over in my direction looking down, and I could see down her shirt. The top few buttons were undone and her breasts were clearly visible. A few thoughts ran through my mind: "Wow", "They're bigger than I thought", "So pert and perky", "I didn't know her nipples were pierced", and "How long have I been staring". By the time I got to the last thought I looked up and noticed Ava looking at me and smiling.