Missed Opportunities

After college I had been spending a lot of time with April. After her kids went to sleep we would play cards and watch movies. Sometimes she would bring up the idea of starting something physical but aside from flirting to some very mild cybering it had never gone anywhere.

One evening we were chatting online and she tells me that she showed my picture to a friend of hers. Her friend Tonya was interested in meeting me, and she said the three of us could hang out sometime.

The next time I went out to visit she invited Tonya over too. The kids were already asleep, and we were in the kitchen at the table. April was already dressed for bed and though Tonya was still in her regular clothes, I guess she was staying over that night. Tonya wasn't shy, and she was flirting a lot during cards. After about a half hour April said she had a headache. I offered to leave but she suggested watching a movie in the dark instead. April had a long couch. Tonya sat down on the end and had me sit next to her. April took up the rest of the couch by propping a few pillows next to my leg and laying down.

About half way through the movie Tonya gently put her hand on my leg. I tried not to react but the thought of her hand being that close started to get me hard. I was a little worried about what April would think. Tonya reached over with her other hand and pulled my hand to her breast. She had a bra on but I could still feel how hard her nipple was through it. I pulled my hand back, shot her a look, and pointed over to April. Tonya grabbed my head, pulled my ear up to her mouth, whispered "she's asleep", and started to kiss my neck. I stopped her and looked over to where April was laying and said her name but got no response.

When I turned back toward Tonya, she was already pulling me in for a long deep kiss. She put my hands on her breasts and started moaning as I touched her. My hands went under her t-shirt so I could undo her bra. She stopped and pulled off her shirt! She moved me closer to her end of the couch and climbed on top of me. My face was buried in her perfect and large beautiful breasts. I was kissing them, sucking at and flicking her nipples with my tongue and started to forget about April being just a few feet over from us until Tonya moved off my lap.

I nervously looked over to where April was but guessed she was just a sound sleeper. Tonya was unzipping my jeans and pulling my cock out. Before she could do much I pulled down her pants a little and put my hand inside her panties while she was giving me a handjob. They were soaking wet... I easily slid a few fingers inside her while she continued working my cock. I glanced back when I thought I heard movement from where April was and then got interrupted by Tonya changing position. She had her mouth all over my cock. I hadn't experienced anything like it since breaking up with my long-term college girlfriend about six months earlier. I was struggling not to cum while she expertly worked me with her hands and her mouth. I didn't want to get anything on April's couch but obviously I had already given up on caring about being caught. I decided to change things up to avoid the inevitable.

I made her stop and stood up. Tonya yanked my jeans down to my ankles and went back down on me. I resisted the temptation to let it keep going and gently pushed her back onto the couch. I was on my knees in front of the couch and started fingering her and used my other hand to play with her nipple again. I realized the position I was actually in. I had my fingers in Tonya's pussy. April's hand was hanging over the couch just inches from my hard cock, and I could have easily moved my hand over to start massaging April's breasts. If she was awake and feeling better, I had wanted a threesome for so long.

Tonya whispered "You really need to fuck me, like right now." I kissed her to buy myself a moment to think and honestly considered going for it. But I didn't have any condoms on me, and I didn't want to wake April up to that sight. Tonya was pulling me closer and trying to grab my cock to get it inside of her. I whispered, "I can't..."

I pulled up my jeans and sat down beside her. I pulled her in to kiss her a few more times as things cooled down. I zipped up my jeans and explained that I couldn't do that to April and that I didn't have a condom on me. The movie had ended awhile ago and I needed to get back to my place which was about a half hour drive.

The entire way home I was kicking myself for not giving in, and I needed to cum in the worst way. It was almost midnight by the time I got home. I took a shower and still couldn't sleep. I laid there and fantasized about April waking up and touching my cock and what might have transpired if I had brought protection and had both women that night. I got myself off and fell asleep but it didn't end there...

April was online the next evening asking if I had a good time. I told her I did. She said, "You do realize I was never asleep, right?" She had faked the headache to move things to the living room. She was breathing deeper while she touched herself and stayed quiet to give Tonya a chance to get things going while convincing me that she was just out. April actually had the condoms ready. If I had agreed to sleep with Tonya, April was going to reach up with a condom and say something like "when you're done fucking her, you're going to fuck me too". The plan was to then move everything up to April's bedroom. I guess when I said that I couldn't and slowed things down, April decided to abort and kept "sleeping" as I said my goodnight and left.

Later on that week I brought up trying to make this happen to April, but she had changed her mind. She was acting jealous and said she didn't want to be in bed with Tonya. She told me if I went off and slept with Tonya on my own time she wasn't sure we could still be friends. Less than a year later I wasn't even talking to April anymore so I had missed both my chance at a threesome and sleeping with Tonya after that night.