When I first wrote about my relationship with Stefan, I incorrectly wrote that our first time having bareback sex was a trip we took in May of the first year we were together. I meant to correct that before I published the story but forgot and I did not expect to write another story about us. But because of responses I received I decided to write about some other moments between us. Our first time having bareback sex actually happened in March of that first year. May was our first long weekend out of town together. For those who haven't read the other stories, I was 34 when this happened. I am 5-10 and was about 155 then. (I'm about 160 now.) I had and still do have short dark hair with brown eyes. Very masc guy and professional. Stefan was 20 with short dark blond-brown hair and blue eyes. He was masc, about 5-6/5-7 and 125-130. His legs were smooth because he shaved them because he was a cyclist. When we met he only shaved a little past his shorts but after being together for a couple months he started to shave all the way up his legs.
This is the story about how our first bareback time happened.
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Stefan first mentioned having bareback anal sex shortly after he returned for the spring semester of the first year we were together. We were laying on a blanket in a very secluded spot on the farm my family owned several miles outside of town. It was a very warm day in early March. I had intended to only make out with him and maybe explore a little oral sex, but one thing quickly led to another. I rimmed him after I worked on his cock, which caused Stefan to beg for me to slide my cock into him. There wasn't a person near us for miles, which Stefan knew, so he began to moan, coo, and tell me how much he wanted me inside of him. Luckily, I had brought a couple of condoms. I pulled one out of my jeans that we had discarded next to us. We made love for at least 30 minutes that day, enjoying the breeze blowing over our bodies and exploring several positions. Because bugs weren't out yet, it was near perfect.
Stefan wanted me to cum on his stomach that day. "Baby, I love to look at you when you spray all over me," he whispered into my ear, right before I pulled out, removed the condom, and shot on him. Then he said the words that made my heart stop as I held him against me: "I would love to have bareback sex with you in front of a roaring fire on a cabin floor. I wanna feel you explode inside me. The thought of that happening drives me insane."
We then talked a lot about what it meant for each of us if we had bareback sex. I explained to Stefan that I considered it to be a big step in a relationship, and I reminded him how we had said from the beginning that our situation was just about having fun because he was going to graduate in a year and head off to med school.
In truth, I had been wanting to have bareback sex with him for a very long time. In fact, from the first time we were together. It already felt incredible to be inside of Stefan while wearing a condom. I could only imagine what it felt like to be inside of him bare. I still hadn't told Stefan that I was in love with him, although I was deeply head over heels in love with this very sexy boy. I didn't want to cause him to lose focus on medical school or anything else. Hell, he wasn't even out of the closet, and at that point no one had a clue we were dating/having sex several times a week. And it wasn't like I was out that much either.
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Stefan brought up having bareback sex again the week before his spring break. It was a night he had come over right after I got in from work. It had been one of those encounters where we undressed one another as we made our way to my bedroom. Before we got into bed, I pushed him against the wall, his back to me. My cock was already lubed from an incredible blow job he had just given me in the doorway, the saliva was starting to lube his ass as I pushed up against him.
"Oh, baby, fuck me right now like this," Stefan moaned while I kissed his neck and rubbed his shoulders. "I want you inside me right now."
I pulled away to reach for a condom in the table next to the bed, what was quickly becoming "our bed".
"No, baby, I want you inside me bare," Stefan said in this little purr that drove me insane whenever he used it on me. "Please."
"Stef, we can't," I said as I reached for a condom and opened it. I could tell by the change in his expression that he was disappointed. I still fucked him while he stood up against my bedroom wall. We eventually wound up on our bed, fucking first doggie and then missionary. When I told him I was getting close he said: "Baby, cum while you are inside me...Please baby." He then pulled my lips to his and I moaned into his mouth while I came into the condom, my cock deep inside him.
"Oh Stef that was wonderful," I said in between breaths, collapsing onto him and kissing his left shoulder.
His hard cock was pressing into me, so I reached down to stroke him while I gave his neck little kisses. Stefan started to play with my hair, his breathing increasing each time I stroked his cock. I kissed down his chest and stomach until I reached his cock, tracing my tongue up his shaft and all over his head. I had his cock in my mouth for less than a minute until he began to shoot. I drained him before I pulled my lips off his cock. I loved the way he tasted. I kissed his body as I moved back toward chest. Although Stefan was smaller than me, I liked it when I rested my head on his chest.
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Stefan played with my hair for a few minutes before saying: "Rick, I'm serious about having bareback sex. It's something I really want to do with you."
"I believe you, Stef," pausing for several seconds, "but before we can consider that, we need to be tested."
"Why? I've only had sex with one other guy, and he used a condom the entire time...Haven't you been safe?"
I told Stefan that I had experienced bareback sex with two other guys, both of whom were longterm boyfriends. The first guy and I had never had bareback before one another, so we didn't bother to get tested. But before the other guy and I had bareback sex, we were tested.
"How long does the test take?" he asked.
"You should know the results before you leave the office. But they will want to "counsel" you about why you should only practice safe sex. The time I was tested, they wanted to talk to both of us about how to practice healthy sex."
"What was that like?" he said. "I mean you said you are not out that much at all but you had to have a talk with a stranger about something like that?"
"It was a little embarrassing, but I didn't mind because it's all confidential. We actually went out of town to be tested because we were more worried about seeing someone there who might suspect something," I said with a half laugh.
There was a short pause, then Stefan said: "I would want to do it that way...leave town."
"Well, if you are really serious about this there is a place about three hours away. I don't think anyone will recognize us, but we can sit in different areas of the room to keep it undercover," I said with another laugh.
"I might actually sit with you there," Stef chuckled and he kissed me on the cheek with his soft lips.
I then worked my way to the top of the bed, so we were nose to nose, laying on our sides. I looked deeply into those beautiful eyes and gave him a long kiss. Stefan's right foot began to trace up and down my left leg while we kissed. After he pulled away from my lips I said: "I would love to have bareback sex with you Stef. I could think of nothing more intimate or intense than to do that with you...But I will warn you, it might cause us to get closer."
"That is what I am hoping," Stefan said, kissing me again. By then our cocks were stiff again, pressing together as we tightened our embraced during the kiss.
"OK," I said, between kisses to his neck, checks and ears, "when would you like to do this?"
"How about this Saturday?"
"I thought your spring break began on Friday. Don't the dorms close?"
"Not for me. I requested to live in the dorms over spring break. I told them I had some special research projects and I got one of my professors to write a note that I needed to be in the dorms over spring break. I told him that I wanted to use that time to study and he was cool with it."
"So you're just going to study over spring break?"
"Actually, I was hoping you would want me to stay here." He grinned that smile that made my heart melt and my cock surge with hardness.
"Fuck yeah, that would be awesome...No chance anyone at the dorm will wonder where you are?"
"Nah, they only have a list of people who are allowed to be in the dorm, I'll need to swing by a few times, but no one will think a thing...So can we get tested on Saturday? Please???"
"Wow, you are eager Stef. Almost as eager as I am," I said as I held him in my arms and kissed him with an amazing amount of passion. Stefan traced his right foot over the back of my legs as I reached for another condom to make love to him again.
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